‘Petty Despots’: The Condottieri Tyrants of Quattrocento Italy


* The images from the Appendix referenced herein are instead spread throughout the text of this essay for easier reading. Enjoy!

When the term ‘Italian Renaissance’ is used, most people think of figures like da Vinci, Michelangelo, Botticelli, and Petrarch; this association with a flourishing of the arts and Western culture is understandable, yet it misses much of the complexity and dynamism inherent in the period, especially during the fifteenth century. That period – known historically as the Quattrocento – was a time of rapid change, political tumult, and dynastic struggle throughout the Italian Peninsula. These geopolitical evolutions were just as radical and revolutionary as were those occurring in the cultural world at the time; in fact, without the political developments of the Quattrocento, many of the cultural aspects of the Renaissance may never have gotten off of the ground. To gain a better understanding of these changes and their impact on society, one must understand the very different political situation in Italy prior to the Renaissance.

Italian history for the few centuries before the Quattrocento was largely dominated by two powerful forces: the Papacy and the Holy Roman Empire of the Hohenstaufens. These factions were mutually reliant on one another for legitimacy as well as rivals for the overlordship of the Italian Peninsula. This conflict defined the late Medieval period in Italy, culminating with the Guelf-Ghibelline wars and vendettas in the twelfth and thirteenth centuries. This all changed in the fourteenth century, however, as the Papacy relocated to Avignon, spiraled into a destructive schism, and lost much of the temporal power formerly emanating from its traditional seat in Rome. With respect to the Holy Roman Empire, a previously dominant power in Italy, the historian Jacob Burckhardt states that “The Emperors of the fourteenth century, even in the most favourable case, were no longer received and respected as feudal lords, but as possible leaders and supporters of powers already in existence.”[1] Upon the return of the Popes to Italy in 1376 and the resolution of the Great Western Schism with the election of Pope Martin V in 1417, the Papacy once again sought to retake its temporal role in Italian politics. However, the Italian world into which this newly invigorated Papacy was returning to assert its traditional role was not at all the same one which it had left in the early fourteenth century. During the period of the ‘Babylonian Captivity’ of the Church, the political situation in Italy had devolved away from a more unified, hierarchical, feudal-type system into a patchwork of independent city-states, statelets, and kingdoms which often were involved in intractable conflicts with one another. The power vacuum created by the flight of the Popes to France and the aloofness of the Holy Roman Empire allowed for the flourishing of local civic identity, the creation of territorial rivalries, and the internecine Italian conflict which came along with them.

In such an atmosphere, ambitious mercenary warlords known as condottieri came to the fore of the political and military worlds, selling their services and their manpower to a wide variety of territorial states, from Florence and Milan to Venice and Naples. These men were not just super-recruiters of armed corps, they led their troops in battle and controlled the tactics, strategy, and logistics of their companies.[2] Indeed, in many ways the condottieri were Quattrocento entrepreneurs, not only due to their independence in contractual matters, but also because they often used their military prowess, cash earned from condotta contracts, and prior family ties to carve out their very own territorial states for themselves and their offspring. This claiming of the right to rule could originate either from existing claims on territories which ran in the family line or could be crafted out of whole cloth by an aspiring condottiere; regardless of the place, these claims were always made at the expense of a general overlord, be it the Papacy or the Empire. Oftentimes these condottieri claimed territory of a local rival to expand their own personal sphere of influence, a tactic which inevitably led to further armed conflict.

At the same time as this political and military dynamism reigned in Italy, there was a flourishing of the classics and a rediscovery of the works, especially literary, of the ancients. This new humanism, which would come to define the Renaissance and presage the Enlightenment, was driven by the widespread reading of classical manuscripts and the scholarship which accompanied it. Writers in the fourteenth, fifteenth, and sixteenth centuries all relied heavily on classical examples, allegories, and texts in their own writing and theorizing, especially when it came to political issues. The long shadow of the Roman Empire cast itself across the entire Italian Peninsula and thinkers, writers, philosophers, and leaders of the time were all living within its cultural context and often near its literal remains. One major topic of interest to these humanists was the idea of ‘tyranny’, a concept quite relevant to the tumultuous political situation in Italy during the Quattrocento as leaders (and even states) were made and unmade in rapid succession, often with great violence. These thinkers wanted to better understand what constituted tyrannical rule, what the proper role for princes or civic leaders should be, how these rulers should behave, and how they gained the legitimacy to hold their titles. All of these important questions were explored through the dual lenses of the classical world and the dynamic polities of the Renaissance. The best way to interrogate this period and understand the vast changes which characterized it is via example; two such exemplars of the condottiere ‘tyrant’ lived during the Quattrocento and were contemporaries, neighbors, enemies, and – via marriage ties – relatives. Federico da Montefeltro of Urbino and Sigismondo Pandolfo Malatesta of Rimini both could be considered ‘tyrants’ of one stripe or another, yet they also could be seen as just rulers with legitimate title. Their interpersonal rivalries, military exploits, cultural patronage, and territorial diplomacy came to define much of what was special and unique about the Quattrocento period in Italy. One cannot, however, delve into these fascinating personages and their governance styles without first understanding the contemporary conceptions of tyranny and legitimacy espoused by the era’s leading humanist philosophers.

Part I: The Idea of Tyranny in Renaissance Italy

Historical Background

The major writers and theorists of tyranny in the late-Medieval and early-Renaissance periods had myriad real-world examples to work with, but two important historical institutions took the forefront in their minds and provide the background for any investigation of tyranny in the Quattrocento: the Papacy, particularly in the centuries preceding the Quattrocento, and the Roman Empire, especially the figure of Julius Caesar.

The development of Italian tyranny in the Medieval period, a process which culminated in the territorial statelets of the condottieri in the Quattrocento, was helped along most by the Papacy. As the Church became an increasingly influential temporal power after the Donation of Pipin in 756, it extended its rule across much of Central Italy, especially in the regions known as the Romagna and the Marches. These fiercely independent, heavily mountainous regions eventually became home to some of the most important condottieri states of the Quattrocento, but what created the conditions for those tyrannies to rise? The easiest answer can be found in the actions and governance of the Papacy over these and other territories under its control. Given the typically advanced age at which Popes were elected, as well as the often wildly different factions which succeeded each other at St. Peter’s, papal governance was inconsistent and weak. As the historian John Larner says, “Every change of pope involved a change in policy, and a change in administrative personnel, and it was difficult to build up any long-term loyalties to personalities or programmes, doomed to be ephemeral by the nature of the state.”[3] Papal government was often feeble and unable to control the intense factional disputes within Italian communes; vendettas and internecine conflict ravaged these regions for decades, if not centuries, due to this power vacuum. Because of this political uncertainty and the frustration it caused in the citizens of the Papal States, people looked elsewhere for leadership and stability to tamp down the civic violence which harmed their communities.[4] They could not, however, look to the other major source of legitimacy within Italy – the Holy Roman Empire – as it had largely been pushed out of the Peninsula as a serious force in the late thirteenth century. The communes of Italy were confronted with a disastrous mix of anarchy – where aristocratic families fought each other for power, prestige, riches, and control – and overweening papal interference. These conflicts were nigh-intractable, so civilians sought a source of local, protective government which could provide calm in an otherwise roiling sea of chaos. Enter the tyrant. According to Larner:

With the failure of the papacy, men must have looked to single-person government as the answer to perpetual aristocratic anarchy. Nor was this all. These men, warriors who had risen to power by their ruthlessness, their skill in war, their cunning, were precisely the men required by their communes to protect them from the novel impositions of papal government.[5]

These warlords were the forerunners of the Quattrocento condottieri tyrants; they seized power without legal justification, ruled by violence, and based their governance on the use of force and their own strength.[6] These earlier Italian tyrants would provide much of the historical basis for the ideological analysis of the Renaissance humanists, but a more ancient example also rang true and influenced their writings.

The Roman Empire, the greatest territorial state to ever emanate from the Italian Peninsula, was the easiest and most common historical reference point for most of those who resided in Italy during the Renaissance. Given its domination of the landscape, the physical remnants it left, and the rediscovery of classical Roman texts, the Empire was a cultural touchstone unlike any other. It just so happens that the progenitor of that Empire, Julius Caesar, was seen as the archetypal tyrant for centuries and was depicted as such by luminaries like Cicero and John of Salisbury.[7] What these men stated about Caesar was unequivocal in its condemnation of his tyranny; John of Salisbury, in his book Policratus, states about Caesar that “Nevertheless, since he had seized upon the government by violence he was regarded as a tyrant”.[8] Cicero himself had similarly harsh words for his contemporary in multiple works; in his treatise on duty, Cicero says that “This has recently been shown by the rashness of Caesar who violated all laws, human and divine, for the sake of that dream of power which his mistaken judgment had conjured up,” whereas in his De Officiis he calls Caesar a “tyrant” directly.[9] These conceptions of Caesar’s tyranny largely passed through the ages unchallenged – until the Renaissance. New humanist scholars sought to collate, describe, and analyze the history and ideology of tyranny as it presented itself in Italy so as to create new models for the Peninsula’s secular rulers. Three men in particular – Coluccio Salutati, Bartolus of Sassoferrato, and Niccolò Machiavelli – challenged and interrogated the classical interpretations of tyranny to craft novel approaches to the age-old question: what is a tyrant?

Renaissance Conceptions of Tyranny and Just Rule

The aforementioned humanist scholars – Salutati, Bartolus, and Machiavelli – conceived of tyranny in two primary frameworks: legalistic and moralistic. Both were important to gain a proper understanding of not just tyranny itself, but also what would make a potential tyrant into a just and moral ruler. The legalistic framework is far more formal and explains much of what makes a tyrant outside of his own behavior, which is covered by the moral framework. First off, Niccolò Machiavelli states that there are three major forms of government – principality, aristocracy, and democracy – which can each be perverted into a corrupt version of itself; principality into tyranny, aristocracy into oligarchy, and democracy into anarchy.[10] As we are concerned with tyranny, our focus will be on discussing principalities and the issues relevant to those states. Machiavelli describes the difference between hereditary and elected princes, claiming the former are generally more corrupt and lead inevitably through their incompetence or malice into tyranny.[11] Although these terms help clarify what form of government a tyranny springs from, they do not define what a tyrant actually is or how one could be so classified. For that, one must look at the writings of Salutati and Bartolus.

These men lived and wrote in the period just before the Quattrocento, so their conceptions of tyranny are neutrally applicable when it comes to the law. Both men begin their treatises on tyranny – “De Tyranno” for Salutati and “De Tyrannia” for Bartolus – with the classical definitions of the term and the etymology of the word ‘tyrant’ itself. Bartolus states that the word “is derived from the Greek word τύροϛ, in the Latin fortis or angustia, wherefore powerful kings were called tyrants. Later it came about that the word was applied to the worst of kings who exercised a cruel and wicked rule over their peoples, that is oppression (angustia), because they oppress (angustiant) their subjects.”[12] The two humanist scholars then continue their works by discussing the definition of ‘tyrant’ proposed by one of the most famous men in the history of Christendom: Pope Gregory I. Gregory the Great, as quoted by Salutati, states that:

Properly speaking a tyrant is one who rules a state without the forms of law…but everyone who rules superbe [autocratically] exercises a tyranny of his own sort. Sometimes a person may practice this in a state through an office which he has received, another in a province, another in a city, another in his own house, and another through concealed malignity, within his own heart. God does not ask how much evil a man does, but how much he would like to do.[13]

Bartolus breaks down Gregory’s definition into its constituent parts, a few of which bear on the Quattrocento definition of tyranny. He states that “As a king or Roman emperor is a lawful and true and universal ruler, so if anyone gains this office unlawfully he is a tyrant in the strict sense,” and follows this up by claiming – with Scriptural backing – that one “is a tyrant because he does not rule according to law.”[14] Bartolus also parses Gregory’s words to resolve whether there is a certain minimum amount of territory ruled over that qualifies someone as a tyrant. He determines that one cannot be a tyrant if he controls only a neighborhood or a few small outlying areas, instead a tyrant must control a polity at least the size of a city, or perhaps larger.[15] Salutati sums up Gregory’s position – and the broad sweep of the legalistic framework – writing that: “The special quality of the tyrant is, that he does not rule according to law; and this may happen in either one of two ways: He may have seized upon a civil government which was not his own, or he may rule unjustly or, speaking more broadly, may pay no attention to the principles of right.”[16] Salutati’s summation touches on the most critical part of the legal framework surrounding the idea of tyranny: that of legitimacy and the validity of one’s title.

Bartolus discusses the importance of legitimacy as well, specifying that a manifest tyrant may become so by having defective title to his realm.[17] As is his wont, Bartolus breaks down in extreme detail the multiple ways in which a ruler can claim power but still have issues with the legitimacy of his title. There are three primary methods which Bartolus describes, all of which are relevant to the tyrannies of Quattrocento Italy. First, “if the city or fortified place (castrum) in which he lives has not the right to choose its own ruler, and one acts there as ruler, he is a tyrant because he is ruling contrary to the law, and he is subject to the lex julia majestatis.”[18] Another means by which one can become a tyrant of defective title is through continuing on in a legitimate office once one’s term has expired or if the overlord who appointed him rescinds the appointment or chooses an alternative official.[19] This would be illegitimate as it removes the power of decision from he who would rightly have it. Finally, there is also a way to become a tyrant of poor title even if the city or territory does have the right to appoint its own ruler; this occurs when the tyrant uses fear or violence to compel or coerce those who elect the leader to choose him over other options.[20] Legitimacy is a constant theme in the humanistic writings about tyranny and forms the basis of the legalistic lens through which to view the condottieri rulers of the Quattrocento. This focus echoes the historical circumstances on the ground quite well; as discussed earlier, Italy was in a state of geopolitical flux, with the two main legitimators – the Pope and the Holy Roman Emperor – vying for power and competing with each other and the local rulers of Italy. The most important temporal power that each faction had within Italy was legitimation: the power to appoint rulers, approve titles, and create new ones. As shown in the works of Bartolus and Salutati, trying to rule with a defective title would cause serious problems for a prince, both internally with respect to their subjects and externally with respect to their peer rulers. Tyrants, as normally understood, were to be overthrown and their edicts ignored; thus, the power to legitimate the titles of various rulers was essentially the power of life or death over a dynasty or prince.

There is one more issue with respect to the legalistic framework: Can one overcome a defective title and avoid being labeled as a tyrant? Opinions differ on this front. Bartolus, in “De Tyrannia”, did not envision a way for a tyrant of defective title to rectify that outside of gaining legitimacy from a proper overlord like the Pope or Holy Roman Emperor. Salutati, on the other hand, has a more nuanced view of the question and espouses it by using the classic exemplar of a ‘tyrant’, Julius Caesar. Clearly, Caesar did not have the right to rule as sole dictator, as he usurped power from the Senate and defended it in a brutal civil war; this makes him a tyrant of defective title by definition. But Salutati does not indeed think that Caesar was a tyrant and points to his deeds and popular acclaim as legitimating forces. Salutati lists the positive characteristics and accomplishments of Caesar, as well as the popular reaction to his rule: Caesar was granted – by the people – titles like ‘Father of the Fatherland’ and ‘Perpetual Dictator’; he was given statues around his temples, a special raised seat in the Senate, and a decoration for his home; and he had a month of the year named for him.[21] Salutati continues by asking an important question: “Can a man raised to power constitutionally and through his own merits, a man who showed such a humane spirit, not to his own partisans alone but also to his opponents because they were his fellow citizens – can he properly be called a tyrant?”[22] His answer to that inquiry is ‘no’, an answer which will play a large role in the conception of tyranny in the Quattrocento.

If the positive actions, attitudes, and deeds of a ruler can transform him from a tyrant into a legitimate ruler, can the opposite also happen? That is, can the deeds of a ruler – one with legitimate title – turn him into a tyrant? According to our humanists, the answer is yes; this is the moralistic framework for interrogating the idea of tyranny. For Bartolus, these sorts of rulers would be considered ‘tyrants of conduct’ versus the prior ‘tyrants of title’. He specifies what sort of rule would constitute tyranny, saying “It should be specially noted that an act of tyranny consists specifically in the oppression of one’s subjects. He is called a tyrant who impoverishes and brings suffering upon his own people.”[23] Bartolus continues by stating that the acts of tyrants include not only oppressing one’s subjects, but also acting to one’s own advantage versus in the interest of the common good.[24] In one chapter of his work on tyranny, Bartolus goes through a list of actions which characterize tyrannies, a list he adapts from Plutarch; the initial register written by the Roman would have indicted nearly all rulers in Trecento Italy, so Bartolus modifies it slightly to excuse those actions he deems justified or lawful. The revised catalog includes such actions as deliberately causing the ruin of capable or wise men, fomenting internal divisions and strife within the polity, forbidding lawful assemblies, purposefully impoverishing his subjects, engaging in unjust wars, and adhering to one faction while punishing all others.[25] For Bartolus, these actions would cause an otherwise legitimate ruler to descend into the pit of tyranny, but not all scholars felt the same way. One of those contrarians was, unsurprisingly, Niccolò Machiavelli.

Machiavelli also believed that the actions of a ruler could constitute tyranny, but he certainly had a different conception of ‘the good’ than did his predecessor Bartolus. For instance, in a passage in his “Discourses” referencing the apocryphal founders of Rome, Machiavelli states a truism that could sum up much of his political philosophy: “It is a sound maxim that reprehensible actions may be justified by their effects, and that when the effect is good, as it was in the case of Romulus, it always justifies the action. For it is the man who uses violence to spoil things, not the man who uses it to mend them, that is blameworthy.”[26] Not only does Machiavelli think that ‘the ends justify the means’, he asserts that sole rulership can often be good: “Wherefore the prudent organizer of a state whose intention it is to govern not in his own interest but for the common good, and not in the interest of his successors but for the sake of that fatherland which is common to all, should contrive to be alone in his authority.”[27] In the privileging of the common good over personal interests, Machiavelli and Bartolus agree. That leads to another question: What is the common good and what sorts of actions make a good ruler? In what many consider his seminal work of political philosophy, The Prince, Machiavelli lays out a laundry list of traits which exemplify a good, just, and successful ruler; these often fall afoul of more typical conceptions of princedom coming out of the long Medieval tradition of the ‘mirror of princes’ literature. In the Medieval conception, princes were supposed to be upright, pious, generous, kind, and fatherly representatives of God and the people; in the Machiavellian conception, cruelty, deception, miserliness, and fear can all be justified if done in the right manner and for the right reason. In Chapter XV of The Prince, he writes that “it is necessary for a prince wishing to hold his own to know how to do wrong, and to make use of it or not according to necessity.”[28] After espousing a veritable inventory of positive and negative personal characteristics, Machiavelli declares:

…it is necessary for him [the prince] to be sufficiently prudent that he may know how to avoid the reproach of those vices which would lose him his state…And again, he need not make himself uneasy at incurring a reproach for those vices without which the state can only be saved with difficulty, for if everything is considered carefully, it will be found that something which looks like virtue, if followed, would be his ruin; whilst something else, which looks like vice, yet followed brings him security and prosperity.[29]

In the next several chapters of The Prince, Machiavelli delves into a variety of princely traits, from liberality to cruelty to faithfulness. His opinion on these issues follows the maxims laid out above; a ruler should act in ways that would preserve his position and that of his principality while avoiding actions that would lose him his state, regardless of the traditional morality of those actions. Occasionally the traditionally moral and the proper princely actions dovetail, as with Machiavelli’s exhortation to avoid being “a violator of the property and women of his subjects”[30] and his attitude towards keeping one’s subjects “satisfied and contented”[31]. Other times they most certainly do not, as in the instances where Machiavelli extols deception and faithlessness in negotiations: “our experience has been that those princes who have done great things have held good faith of little account, and have known how to circumvent the intellect of men by craft, and in the end have overcome those who have relied on their word.”[32] Both Machiavellian and traditional morality can be found in the examples of the Quattrocento condottieri, oftentimes within the same personage and state.

One characteristic of the good ruler on which all scholars could agree was patronage of high arts, culture, and humanistic literature. Renaissance princes found the concept of glory or fame to be of crucial importance, partially due to the blossoming of humanism during this period. As works previously thought lost to posterity were rediscovered, they helped to change the popular conception of the relationship between the past, present, and future. More and more, major political figures came to fully comprehend the importance of creating a lasting legacy beyond their own offspring; this crafting of fame would see its full flowering in the patronage of the arts and of literature, two mediums which stand the test of time. The Courts of the Quattrocento would compete with each other for glory and fame, as well as the scholars, writers, and artists who could provide it.

Coluccio Salutati does an excellent job of summing up the two frameworks – legal and moral – through which people of the Quattrocento understood tyranny: “We conclude, therefore, that a tyrant is either one who usurps a government, having no legal title for his rule, or one who governs superbe or rules unjustly or does not observe law and equity; just as, on the other hand, he is a lawful prince upon whom the right to govern is conferred, who administers justice and maintains the laws.”[33] When these seemingly clear definitions are applied to the condottieri rulers of the Quattrocento, however, things become far more complicated; reality often defies even nuanced definitions like those of Salutati, Bartolus, and Machiavelli.

Part II: The Condottieri ‘Tyrants’ of the Quattrocento

The complexity of the contemporary definitions of tyranny was mirrored by the men who were labeled with that term during the Quattrocento; the two examples presented below showcase the wide variety of personalities, predilections, and governance approaches that were taken by rulers in the period. Federico da Montefeltro and Sigismondo Malatesta were complicated figures who cannot be easily categorized as ‘tyrant’ or ‘not tyrant’. They each were sole rulers with princely powers in their domains, had various issues of legitimacy of title, had their own moralistic failures and successes, and encouraged and led a flourishing of the humanistic arts in their principalities. Perhaps most importantly, they were both immensely triumphant in the arts of war, something which helped them finance and solidify their temporal power and territorial reach. These condottieri lords fought against and with each other at various points in their overlapping careers, and were tied together by bonds of family, marriage, and contract. Both spent their lives and careers in Central Italy, had deep – and sometimes controversial – relationships with the Papacy, and involved themselves in the same Italian conflicts. Despite these similarities, the two men – who led Urbino and Rimini – were supremely different; these distinctions allow them to serve as real-life exemplars of the theoretical discussions of tyranny engaged in by humanists like Salutati, Bartolus, and Machiavelli.

The best way to understand the disparate, yet parallel, lives of these condottieri ‘tyrants’ is through comparing them on the same basic terms. Dividing the aspects of their lordships into three categories – internal affairs, external affairs, and intellectual and cultural life – allows one to grasp more fully the various dimensions of tyranny exhibited by each man’s reign. The first category of internal affairs covers important factors like the legitimacy of title, the treatment of subjects, the control of territory, personal traits, and how each gained his domain. With respect to external affairs, this includes their military careers as condottieri, their diplomatic and martial dealings with other Italian (and outside) powers, their political marriages and alliances, as well as the enmities they created. Finally, intellectual and cultural aspects deserve their own section; this contains the patronage of art and literature, the use of architecture as an aspect of rule, the humanistic leanings of the lords, their propaganda campaigns, and – perhaps most crucially for the Quattrocento – their attitudes towards religion. By looking at the careers and actions of these men in detail, one can see how tyranny was both commonplace and hard to define in Quattrocento Italy, how it impacted the politics and development of the region, and how different approaches to governance could succeed – to varying degrees – in crafting a lasting legacy, if not a stable dynasty.

Federico da Montefeltro, Duke of Urbino

Figure 1: Portraits of the Duke and Duchess of Urbino, Federico da Montefeltro and Battista Sforza; Piero della Francesca, Portraits of the Duke and Duchess of Urbino, Federico da Montefeltro and Battista Sforza, 1470, tempera on wood, 47 cm x 33 cm (18.5 in x 12.9 in), Uffizi Gallery, Florence, Italy.

The first example of a condottieri ruler whose career represents aspects of the Quattrocento conception of tyranny is the one who has had the most favorable historical picture painted of him: Duke Federico da Montefeltro of Urbino. This duchy was picturesquely described by the writer Baldassare Castiglione in his famed work, The Book of the Courtier: “On the slopes of the Apennines almost in the center of Italy over toward the Adriatic Sea is situated the little city of Urbino…Although it is among mountains, and not such pleasant ones perhaps as some others which we find in many regions, still heaven has so favored it that the countryside roundabout is very fertile and fruitful.”[34] In the passages following that depiction of Urbino, Castiglione extols the virtues of the former duke of that city, Federico da Montefeltro. Federico was born in 1422, most likely the bastard son of the then-ruler of Urbino, Guidantonio da Montefeltro, although his birth story is shrouded in mystery; over the centuries several different paternity and maternity stories were posed about Federico’s birth, but it is probable that he was the illegitimate son of Guidantonio and an unknown woman.[35] These paternity questions would be used by Federico’s rivals in Italy – including Sigismondo Malatesta – to diminish his legitimate claim to power in Urbino, something which could push him more firmly into the tyrant camp. As an illegitimate son – he was legitimated by papal fiat in 1424 – he was seen as a secondary figure by his family and was given as a hostage in various negotiations to both Venice and Mantua; in these impressive Renaissance courts, Federico was treated well and educated as though he was a part of the local ruling class. He took over as Lord of Urbino from his legitimate half-brother Oddantonio after the latter was assassinated by citizens angry with his cruelty, high taxes, profligacy, and hedonistic lifestyle.[36] Upon his succession, Federico “agreed to comply with the wishes of his subjects” and made agreements with them to promise good governance.[37] The specifics of the agreement read almost like a checklist for virtuous lordship; Federico swore to grant a general amnesty, lower taxes, reform government practices and bureaucracy, pay outstanding ducal debts, institute a health service for the town, and create a more formal education system for the citizenry.[38] These contractual promises made with the citizens of Urbino, as well as the conciliatory approaches Federico made towards the Pope, were an important part of the legitimation process for Federico to have rightful and proper lordship over Urbino.

Federico also gained acclaim – and legitimacy – from his governance of Urbino; besides the promises he made – and kept – when taking power, Federico calmed the civil unrest in the territory within two years after his accession, earned significant funds from his condottiere career, and spent that money wisely and for the benefit of Urbino’s citizens. [39] According to his contemporary and friend, the humanist writer and bookseller Vespasiano da Bisticci, Duke Federico treated his subjects as though they were his children, a paternalistic attitude that was seen as the height of benevolence at the time.[40] He was open to speaking to his subjects at any time and about any grievance, letting them dine with him and speak freely in his presence.[41] Federico also was forgiving of many civil and criminal offenses if the perpetrator confessed and repented – the lone exception being blasphemy, something which showcased his pious nature.[42] Vespasiano states that “The country he ruled was a wondrous sight: all his subjects were well-to-do and waxed rich through labour at the works he had instituted, and a beggar was never seen.”[43] These descriptions of his governance reflect the attributes of his character that were most prevalent: honesty, loyalty, humility, openness, intelligence, generosity, and sound-mindedness. In his personal life, the Duke was just as faithful; he was not an infamous philanderer as were most of his contemporaries (he only fathered four bastards) and he married twice, both for love as much as politics.[44] His second wife was Battista Sforza, a cultured and intelligent woman who would help him run his state as well as create a prominent and opulent court life.[45] His love and respect for her as a peer was serious and comes through even in painted diptychs (Figure 1, see Appendix) which he had displayed prominently in his Ducal Palace. Federico’s most important and unique quality, the one which won him admirers at the time and through the ages, was the same one which catapulted his condottiere career into the stratosphere: his good faith.

In the profession of condottiere, loyalty and willingness to stay faithful to one’s contractual commitments was crucial to lasting success and the creation of positive alliances and relationships. Duke Federico had both in spades, largely due to his legendary constancy; in an anecdote relayed by Vespasiano, Federico was approached by the Venetians with an offer of eighty thousand ducats (a very handsome sum) to turn on his employers at the time – a political league comprised of Florence, Milan, and Naples – a gift he refused. In response to the Venetian messenger’s statement, “Eighty thousand ducats is a good price simply for staying at home,” Federico replied, “To keep faith is still better, and is worth more than all the gold in the world.”[46] This faithfulness made the Duke of Urbino a highly sought-after commodity in the world of Quattrocento warfare; his nearly-unblemished military record assuaged any other concerns a prospective employer may have.[47] Federico earned money as a condottiere for nearly thirty-four straight years, providing a steady stream of income for his duchy and its citizens; according to the scholar Geoffrey Trease, “Military service was the invisible export that balanced the budget.”[48] Federico fought with patience, tact, and calculation, often taking time to ensure success before attacking – unlike some of his more rash contemporaries. His strategizing did not necessarily make him immune to the acts of brutality and cruelty which were unfortunately commonplace in Quattrocento warfare; the vicious sack of a Tuscan town named Volterra was an orgy of violence, rape, pillage, and plunder before it was put to a stop by the Duke.[49] Still, Federico’s service, gallantry, and military success were honored by rulers across Italy and Europe more widely, as he earned accolades from the Papacy, Naples, Milan, Florence, and even England[50]; these honorifics he often displayed on his emblems, including the crossed keys of St. Peter and the golden rose of the Pope, the Order of the Ermine from Naples, and England’s Order of the Garter.[51]

These high honors tell one just as much about Federico’s diplomatic ability as they do his martial proficiency. Urbino was a small duchy, only forty miles by forty miles[52], and was located right in the middle of far larger and more powerful territorial states – including the Papal States, Naples, and Florence – and their disputes. Federico’s approach was to balance the powers of Italy against each other to achieve some semblance of calm for his duchy, something at which he was quite successful. The Duke was well-known as a shrewd diplomat who protected the prerogatives of his native Urbino, as well as the interests of his allies and employers, against the encroachments and challenges of his rivals. One such notorious rival was Sigismondo Pandolfo Malatesta, the lord of nearby Rimini, who constantly fought Federico over territories disputed between the two statelets; Federico’s tact, discipline, and faithful personality helped win allies to his cause against Malatesta. Montefeltro’s diplomatic acumen was not only used for positive means; documents have been uncovered which tie him directly to the infamous Pazzi Conspiracy, in which the plotters attempted to murder the Medici family in Florence.[53] The historian Marcello Simonetta darkens the bright portrait that contemporaries painted of the Duke, stating that “Federico did not entertain any moral scruple, and pursued his project of creating a monument to culture – and to himself. He epitomized refined taste and ruthless politics.”[54]

The most important ally that supported Federico through most of his life and career was the Papacy. The Duke had long-standing ties to the Papacy through his family lineage and served the Popes often as condottiere; he was Captain-General to three Popes and was awarded the title of Gonfalonier of the Church, bearing the Papal flag and insignia into battle on many occasions.[55] Federico used these ties and his service to his full benefit, receiving major favors from Pope Pius II, including grants of further territories, explicit protection of the Church, and actions taken against his rival Malatesta; after Pius’s death in 1464, Federico remained close to the Papacy and was legitimated as Duke in 1474 by Pope Sixtus IV.[56] The relationship with the Papacy was critical for the continuation of the Montefeltro line as legitimate rulers of Urbino, as the Popes were one of two greater sources of legitimacy in Italy; keeping as much as possible on their good side was necessary for the dynastic continuity of the Montefeltro clan. Although he was closely allied with the Papacy, Federico was still Duke of Urbino first; he actually turned on the Papacy for a time in 1469, allying with the successor to his late rival Sigismondo Malatesta in order to protect Rimini from papal annexation.[57] This change of heart and the successful military defense of Rimini against the Pope’s armies exemplifies Federico’s astuteness in political affairs, as he felt the Pope would be too powerful if the Papal States gained this territory and resolved to keep a balance of power so as to secure his own dynastic position – if Rimini fell, Urbino may have been next.

Figure 2: Portrait of Federico da Montefeltro and His Son Guidobaldo; Pedro Berruguete, Portrait of Federico da Montefeltro and His Son Guidobaldo, 1476, tempera on wood, 138.5 cm x 82.5 cm (54.5 in x 32.5 in), Galleria Nazionale delle Marche, Urbino, Italy.

Federico of Urbino was not only widely praised for his internal governance and his martial prowess, he also created one of the era’s greatest court cultures, patronized many humanistic scholars, and assembled the most impressive library of the Renaissance. The Duke’s obsession with cultural and intellectual pursuits began at a young age, during his education at the Gonzaga court of Mantua under the famed humanist tutor Vittorino da Feltre[58]; at this court the young Federico learned the liberal arts alongside the martial ones, and da Feltre wrote that that Federico was his favorite pupil.[59] The Duke of Urbino backed up his passion for the arts with his wallet, spending more money in less time on the arts than any other prince in Quattrocento Italy; for instance, he spent over twenty-five-hundred ducats on tapestries alone.[60] He patronized an assortment of famous and influential figures, including painters like Piero della Francesca (the artist of the diptych in Figure 1) and Justus of Ghent, architects like Leon Battista Alberti and Luciano Laurana, and a wide variety of scientists, mathematicians, astronomers, and writers.[61] According to the historian Jonathan J.G. Alexander, “The purpose of Federico’s artistic patronage was…emphatically an exercise in public relations, not just the private whim of a cultivated art lover.”[62] The most outward-facing of Federico’s humanistic cultural projects was his ancestral home and the seat of his power, the Palazzo Ducale, which Castiglione called “the most beautiful to be found in all Italy.”[63] Although the building itself existed before Federico’s accession, he carried out a massive renovation; not only did he contract with Laurana for the work, he was deeply involved in its day-to-day progress, as can be seen in an extant letter he wrote to the architect detailing his expectations.[64] The letter showcases Federico’s knowledge and interest in architecture, and the Palazzo he envisioned exemplified that care. The Palazzo was as much a political project as it was an architectural one, and was directly related to contemporary ideas about tyranny and architecture. The theorist and architect Leon Battista Alberti “wrote that a wise ruler builds a palace and situates it in the center of town where it is accessible to the citizens. A tyrant, on the other hand, builds a fortress which may be physically inside the town, but is separate by virtue of being walled off and inaccessible.”[65] Urbino’s Palazzo was designed precisely to fit the mold of a just and legitimate ruler, as it was relatively open and combined power with accessibility, crafting a truly Renaissance image.[66] This openness was welcoming to the citizens of Urbino, symbolizing Federico’s rule itself, and allowed his subjects access to nearly the entire Palazzo but for the private residence of the family.[67]

The crowning achievement of Federico’s humanistic court was not the Palazzo itself, but the treasures which resided within it: the Montefeltro library. According to Vespasiano, Federico “alone had a mind to do what no one had done for a thousand years or more; that is, to create the finest library since ancient times.”[68] The library contained over nine hundred manuscript volumes, covering classical works, Medieval philosophy and theology, literature and poetry, Scripture, and contemporary treatises on a wide variety of topics.[69] As per Marcella Peruzzi, a scholar of the Montefeltro library, “Each and every artistic and cultural product at Urbino was programmatic: nothing was left to chance.”[70] Federico also commissioned artworks that glorified the library and presented himself as a cultured, literary figure who through his good governance and cultural excellence was a legitimate ruler. This can be seen in the portrait of the Duke with his son and successor, Guidobaldo (Figure 2), where Federico is depicted reading a book in his library while surrounded by the insignia and emblems of power – his armored helmet, a hat associated with the Church, and the scepter of power held by his son. Many of the works in the Urbino library were specifically commissioned by the Duke to glorify and legitimate his rule, a common practice at the time. In the words of Peruzzi, “Each commission carried with it a precise message; that delivered by the construction of a library concerned the role that humanistic culture, whose focal point was not only man but also God, should have in matters of state governance.”[71]

Although he had his issues with legitimacy, many contemporaries and historical scholars see Federico da Montefeltro as the archetype of good governance of the Quattrocento in the Salutati and Bartolus mold; Vespasiano sums this up well, saying “It is long since Italy had known a prince so worthy of imitation in every respect as the Duke of Urbino.”[72] The other example of a Quattrocento condottiere ruler was Federico’s polar opposite in nearly every respect.

Sigismondo Pandolfo Malatesta, Lord of Rimini

In terms of his historical reputation, Sigismondo Pandolfo Malatesta, the Lord of Rimini, is the antithesis of his counterpart in Urbino; if Federico da Montefeltro was defined by his positive characteristics, Malatesta was distinguished by his negative associations. Most of these negative images which make up the so-called ‘Black Legend’ of Sigismondo Malatesta come from a single source: Pope Pius II. Pius absolutely despised Malatesta and did everything within his power to destroy the Lord of Rimini, including damning him to Hell – while he was still alive – in the only reverse canonization in the millennia-long history of the Roman Catholic Church.[73] In a papal bull replete with invective castigating Sigismondo for heresy, blasphemy, murder, treason, and incest, Pope Pius II states:

We excommunicate him again, call him anathema, and judge that he is to be cut from the body of the militant church like a putrid limb; and we forbid him to have any contact or commerce with the entire church of Christ, as if he were a sick and infected sheep. Unless he comes to his senses before leaving that muddy prison of the body, we allow his soul to be tortured by cruel demons and burned in the eternal flame.[74]

Pius, in his Commentaries, accuses Malatesta of several heinous acts and traits, saying that “in cruelty he surpassed all the barbarians,”[75] and listing several alleged incidents of rape, necrophilia, sodomy, and murder – even alleging that Sigismondo murdered his elder brother and his first two wives.[76] This is the reputation which has dogged the name of Sigismondo Pandolfo Malatesta through the centuries, but is it true? Was the Lord of Rimini truly the perfect avatar of Quattrocento tyranny? As is expected, the truth is far more nuanced and interesting than the myth.

Figure 3: Medal, Bust of Sigismondo Pandolfo Malatesta (obverse) and Bust of Isotta degli Atti (reverse); Matteo de’Pasti, Medal: Bust of Sigismondo Pandolfo Malatesta, circa 1447 (model), copper alloy, 8.4 cm diameter x 294.21 g weight (3.3 in diameter x 10.38 oz weight), Metropolitan Museum of Art, New York City, USA.

Sigismondo Pandolfo Malatesta, born in 1417, was, like Federico da Montefeltro, the illegitimate son of a ruler – in this case, Pandolfo Malatesta, Lord of Fano.[77] Upon his father’s death in 1427, Sigismondo was put under the guardianship of his uncle Carlo, the Lord of Rimini, where he was educated in the Mantuan style – Elizabetta Gonzaga of Mantua was Carlo’s wife – and raised to eventually become a lord himself.[78] Legitimacy was an issue for Sigismondo throughout his life, and it started early; he was legitimated by Pope Martin V in 1428, a prerequisite for inheriting any Malatesta domains.[79] The legitimation happened just in time, as Carlo died only a year later; as the elder heir, Sigismondo’s pious and saintly brother Galeotto was named Lord of Rimini, but he was ill-suited for the job.[80] Galeotto was ascetic to the extreme and was far more interested in religious life than he was in the politics of Quattrocento Italy; this was the reverse of his younger brother. Sigismondo was tested early on in his brother’s brief reign, as he was tasked with defending Rimini from invading papal armies at the tender age of thirteen – he was successful, presaging an impressive military career.[81] Galeotto died in 1432, making Sigismondo the rightful ruler of Rimini, but his problems were just beginning. Sigismondo was confronted with further territorial incursions, this time from a rival branch of the Malatesta clan. He was successful in fighting off these would-be usurpers and kept Rimini independent, acts which gained him the support and love of the citizens of the seaside town.[82] These attempts at dispossessing him would not be forgotten by Sigismondo; he spent much of his life working towards legitimation of his dynastic title and independence from the Papacy.[83]

One event which deeply influenced the young ruler of Rimini was the visit of the Holy Roman Emperor, Sigismund, to Rimini in September 1433. During this visit, Sigismondo and his younger brother Domenico were knighted by the Emperor, and the former changed his name after the honor – the Italian name Gismondo became the new Sigismondo to pay tribute to the Emperor’s visit and more formally associate the Malatestas of Rimini with the Empire.[84] It would turn out that this would be the only imperial honor ever granted to Sigismondo, despite his lifelong attempts at gaining a clear title and proving his dynastic legitimacy.[85] This knighting and Sigismondo’s fixation on the important event helps to debunk a commonly-held myth about the ruler: that of the origin of his intertwined ‘SI’ emblem. For centuries, scholars believed (and many still do) that the letters ‘SI’ represented Sigismondo’s self-obsession; it was thought that the ‘S’ stood for Sigismondo and the ‘I’ for his third wife and long-time mistress Isotta degli Atti, the intertwining of the two meant to elevate Sigismondo and his wife to emblematic status.[86] In fact, the intertwined letters stand for the first two letters of his new name and serve to tie him further to the Emperor in an effort to create legitimacy.[87] This quest for legitimacy would dominate the rest of Sigismondo’s life; he tried to gain it through many means which the humanist scholars of tyranny would find familiar. According to the scholar Helen Shahrokh Ettlinger, Sigismondo understood the humanist conceptions of tyranny and legitimacy and tried to, through demonstrations of his virtù, “lay the groundwork for eventual independent and legitimate rulership by [his] own efforts.”[88] Malatesta attempted to rule his subjects justly, and by all local accounts he succeeded; despite the vitriolic rhetoric of Pius II, the people of Rimini seemed quite pleased with their Lord and did not rebel against him even through a series of defeats, embarrassments, and excommunications later in his life.[89] Due to his exploits as a condottiere, his taking of important trade routes and the concomitant taxes and tariffs which went along with them, and his treacherous behavior with respect to payments owed others, Rimini became more prosperous (even as Sigismondo himself was chronically short of funds).[90] This increased economic vitality and independence was crucial to the success of the Malatesta project of gaining greater legitimacy and autonomy for themselves and Rimini.[91] Sigismondo’s fame and his patronage of the arts also helped improve the contemporary reputation of Rimini, previously known mostly for its port, its sleepy seaside location, and its Roman heritage – it boasted an arch commissioned by the Emperor Augustus, a glorious reminder of a history that Sigismondo would seek to surpass.[92]

One of the biggest hurdles facing Sigismondo in his quest for fame, glory, and legitimacy was his own volatile and unreliable personality, which manifested itself in his personal, professional, and military life. This does not fully vindicate the stories crafted by Pius II, but they would have been believable given the evidence which did exist in fact. Sigismondo was most of all a deceiver, something which he was seemingly quite proud of[93]; in literary works he commissioned to exalt his virtues, he allowed the writers to represent him as a trickster, foreshadowing the Machiavellian conception of the good ruler as having the duplicity of a fox.[94] Another portion of The Prince that Malatesta prefigured was Chapter XVII, where Machiavelli discourses on “whether it is better to be loved or feared,” coming down on the side of fear if one must choose.[95] Sigismondo’s opinion on this age-old question is preserved in an epic poem – the Hesperis – by the writer Basinio, a member of the Riminese Court, which states, “When people criticize you [Sigismondo] for being both too lenient and sometimes appearing too severe and cruel, you usually respond that cruelty is unbecoming in a prince but that in order to be victorious the commander of an army has to be feared more than the enemy.”[96] This approach is almost exactly what Machiavelli was advocating in his treatise more than half-a-century later. In fact, Sigismondo’s life was essentially a near-perfect exemplar of the Machiavellian conception of the prince, complicating his status as a potential tyrant. The Malatesta clan throughout history was associated with violence, turbulence, inconsistency, vigor, fortitude, licentiousness, and intellectual and cultural curiosity; “In Sigismondo Pandolfo Malatesta, the Malatesta characteristics reached their ultimate and most brilliant development,” for better and for worse.[97]

A good study of Sigismondo’s personality features and flaws comes from exploring his romantic liaisons and marriages. The Lord of Rimini was married thrice and was betrothed four times; he was initially engaged to be married to the daughter of a fellow condottiere, the Count of Carmagnola, but broke off the commitment after the Count’s death – he did, however, keep the already-paid dowry for himself.[98] His first two consummated marriages were political affairs, as he wed Ginevra d’Este of Ferrara in 1434 and then Polissena Sforza of Milan in 1441.[99] Both women died – Ginevra after a difficult childbirth and Polissena after a bout of plague – and Sigismondo was accused by Pius and several of his contemporaries of murdering both.[100] Malatesta did have several mistresses and multiple bastards during each of those marriages, but there is no serious evidence that he had anything to do with either of his wives’ deaths; it is likely that the charges were invented as part of a scheme to diminish Sigismondo’s power for the profit of the Pope and several of Malatesta’s rivals – including Federico da Montefeltro and Francesco Sforza of Milan.[101] Sigismondo’s third and final wife was the love of his life, Isotta degli Atti. The two met and began an extramarital affair when she was fourteen years old; the odd part of this was not the fact of the affair itself, as this was normal for the age, but of its widespread publicity and its embrace by Sigismondo in his public life.[102] He even went so far as to commission a commemorative medal depicting his own face on the obverse and that of Isotta on the reverse (Figure 3); this was marked with the starting date of their romance, even though Malatesta was then married to another woman. Another uncommon aspect of the love affair and eventual marriage was the lack of political utility therein; Isotta’s family was a well-established Rimini clan, but there was no political upside to the match.[103] Marrying specifically for love was extremely rare among the nobility of the Quattrocento – everything was seen through a political lens – but Sigismondo was not exactly enamored with being ‘normal’.

Sigismondo’s mercurial personality was of prime importance when it came to his dealings outside of Rimini; his career as a condottiere, his interactions with other Italian powers, and the disdain with which he was seen by the end of his life all stemmed directly from his volatile and deceitful behavior. As stated by Jacob Burckhardt, “Unscrupulousness, impiety, military skill, and high culture have been seldom combined in one individual as in Sigismondo Malatesta”[104]; he was correct in this assessment, particularly when it came to external affairs. Sigismondo’s career as a condottiere was mixed, even though his prowess in the realms of strategy, tactics, military engineering, and battlefield leadership was nigh-unparalleled[105]; still, his various employers had serious issues with getting him to follow their orders and his acerbic personality made working with him very difficult.[106] When it comes to his actual record in battle, Sigismondo was indisputably one of the best condottieri of the Quattrocento. He was triumphant in the Tuscan Wars of 1448 and 1453, conflicts which set the stage for the rest of the century in Italian politics, and was heralded for defending Florence from the Aragonese of Naples, as well as liberating the city of Piombino from a severe siege in 1448.[107] The liberation of Piombino was a major victory for Sigismondo, as he was outnumbered – he commanded between eight and nine thousand men to Aragon’s fifteen thousand – bucked conventional wisdom (including that of Montefeltro) to wait until the right moment to attack, and won the day by outflanking his opponent.[108] Sigismondo’s military skill – and his potential for brutality – was also evidenced by his sack of the fortified city of Crema during the Second Tuscan War, where he “burned fields, destroyed houses, and took prisoners and livestock; he devastated every part of that land, then dried out its marshes. Its walls had never before fallen under any attack, even an imperial one. The inhabitants obeyed [him] as their conqueror and many other difficult places caved under [his] efforts.”[109] Several contemporary sources praise Sigismondo for his ingenuity in military affairs, including his unique use of artillery, his invention of various siege engines and explosives, and his excellent use of cutting-edge military engineering, particularly in field fortifications.[110]

Nevertheless, according to the author Anthony D’Elia, “Despite or perhaps because of his successes, however, Sigismondo spread himself thin, had too many different employers, and consequently lost trust.”[111] Given the difficult geopolitical position of Rimini, “a small state ringed with greedy neighbours,”[112] Sigismondo’s personal attitude and frequent faithlessness made him enemies that his state could not survive. He strove, as did Federico da Montefeltro, to balance the powers of Italy against one another so as to retain and expand his territorial state – a state which was surrounded by more powerful counterparts: The Papacy to its south, Florence to its west, Milan in the northwest, and Venice in the north.[113] Sigismondo’s personality and behavior made it impossible for him to succeed in this goal in the long-run. His inconstancy was one of his only constant traits; Sigismondo betrayed more employers and potential allies than any other condottiere of the Quattrocento. He often took money from an employer and remained at home or used the funds for his own political purposes, as well as switching sides when a better deal came along – in this, he was the complete opposite of his counterpart in Urbino. Although some betrayal was understood to be part and parcel of the condottiere life[114], Sigismondo took this to the next level and was not known to follow the conventional code of honor that many of his peers took seriously.[115] Sigismondo repeatedly put his own territorial aspirations above the goals of his employers, something which irked them and lowered his reputation over time[116]; other condottiere like Federico da Montefeltro took a longer-term view, subordinated their immediate personal wishes to the condotta contract, and ended up gaining allies when it did eventually come time to satisfy his personal objectives. Helen Shahrokh Ettlinger sums Sigismondo’s problem up well: “There can be little doubt, of course, that in an era of skillful statesmen, Sigismondo lost a great deal of respect through his own stubbornness and lack of self-control.”[117]

The most important blunder of Malatesta’s career, and the one which launched his downfall in Italian politics, was directly as a result of this greed, deception, and short-term thinking. In 1447, Alfonso of Aragon, the King of Naples, contracted with Sigismondo to fight against the Florentines for a sum of thirty thousand ducats; Malatesta pocketed that cash and spent his time making inroads on Montefeltro territory instead of working to accomplish Aragonese goals.[118] He tried to explain this away to Alfonso by claiming that attacking Urbino’s lands would cause Federico – then employed by the Florentines – to leave the field and return to defend his patrimony.[119] Alfonso rejected this argument and exhorted Sigismondo to live up to his contract and join the fight. Unfortunately for him, Sigismondo took his advice, but joined the Florentines instead of his initial employer in Naples.[120] Once joining the Florentines, Malatesta had his great success at Piombino, which both “made his reputation as a shrewd military tactician and brave warrior,” as well as sealing his ultimate fate.[121] Alfonso never forgot this betrayal and held his grudge for the rest of his life; this redounded to the detriment of Sigismondo when Alfonso made certain that the Lord of Rimini was excluded from the 1454 Peace of Lodi, which guaranteed a period of armistice between the major powers of Italy.[122] As Sigismondo was specifically excluded from the treaty, Alfonso had total license to attack his possessions and work to destroy the Malatesta dynasty; the other powers of Italy acceded to this request as the powerful Naples was a much more important ally than was the inconsistent and volatile petty despot living on the shores of the Adriatic.[123]

Sigismondo had similarly bad relationships with many of the other leaders of the time, from Federico da Montefeltro to Francesco Sforza to Pope Pius II. He further lost respect and gained antagonism from his Italian counterparts for his dalliances with foreign powers; in Quattrocento Italy, it was generally agreed that keeping external threats – including the Holy Roman Empire, France, and Spain – at arm’s length was the best approach to maintain the relative autonomy of the Italian states. Sigismondo lost a long-time ally in Francesco Sforza for just this reason; the Lord of Rimini supported the French dynastic claim of the Angevins to Naples and invited that foreign power into Italy to pursue those claims.[124] This specifically bothered Sforza because that same French line had serious claims to his own domain, the duchy of Milan; given the immense importance of legitimacy in Quattrocento Italy, Sigismondo’s action was an attack on the very foundations of Sforza rule in the north. The Lord of Rimini further inflamed tensions with his Italian counterparts by his flirtations with the most dangerous enemy to Western Christendom: the hated Turks. After his initial excommunication by Pius II, Malatesta was lacking allies in his mission to defend Rimini and his remaining territories; he thus tried to form an alliance with the man who sacked Constantinople and destroyed the remnants of the Byzantine Empire, Ottoman Sultan Mehmet II.[125] This was not just a random idea which Sigismondo never followed up on. In fact, he attempted to facilitate the threatened Ottoman advance into Italy by sending the Sultan maps of the peninsula’s coasts and treatises on Italian warfare[126]; this was an unforgivable sin in an era where Turkish domination of Italy was a clear and present danger. Finally, Sigismondo truly made himself a powerful enemy when he took up arms against the Pope and refused to follow his edicts. The ‘Black Legend’ of Pius II was discussed earlier, but it would never have been written if not for Sigismondo’s antagonism. As detailed above, most of the moral charges against Malatesta were factually inaccurate and wildly exaggerated; Sigismondo’s ultimate heresy was political, not religious.[127] Malatesta refused to evacuate Papal territory which he had conquered[128], and may have used heretical ideas like those of Jan Hus to contend that the Pope had no business acting in the temporal realm.[129] These assertions were impossible for the Pope to countenance, but he needed further charges to justify the exceptional treatment which he had planned for Sigismondo – charges which he found evidence for in the Lord of Rimini’s humanist fascination with classical paganism.

Sigismondo Malatesta was a prolific patron of the arts, architecture, and culture in Rimini and across Italy, but his efforts often fell afoul of the religious attitudes of the time. According to Anthony D’Elia, “Pagan themes are ubiquitous in the brief cultural flowering of mid- fifteenth-century Rimini…in Sigismondo Malatesta, the Renaissance engagement with classical antiquity takes its most extreme form.”[130] The Lord of Rimini patronized a wide variety of humanists, from literary figures like Valturio and Basinio to painters like Piero della Francesca and architects including Leon Battista Alberti; he had a particular interest in philosophy and translation, particularly from the Greek. Rimini, despite its small size, was one of the major Renaissance centers of Greek learning and Hellenistic culture in Italy[131]; Sigismondo “made the study of Latin and Greek literature central to the culture”[132] of his court. Malatesta would involve himself quite often in the disputations and discussions of classical works and philosophical problems which characterized his court, showing that he had a level of curiosity and intelligence which seems at odds with the ‘Black Legend’. He commissioned several important works of literature, especially the Hesperis of Basinio, which mimicked the style and language of Greek epic poems like Homer’s Iliad and Odyssey.[133] These works were not only Hellenistic in style, they were unabashedly pagan in verse[134]: the Hesperis especially includes invocations and comparisons to the gods of Greece and Rome. This classical imagery and form were also present in the works he commissioned – and wrote himself – to glorify and adore his beloved Isotta.[135] Much of the imagery of these poems was taken directly from the odes and poems of Greek antiquity. Sigismondo was not only a fan of Greek literature, but likewise of their classical philosophy and its more modern forms; he commonly was thought to prefer the Neo-Platonism of the Byzantine philosopher Gemisthus Plethon to Christianity.[136] He was so enamored with Plethon that he took the time, while on a semi-crusade against the Turks in Greece near the end of his life, to save the philosopher’s bones from desecration and bring them back to Rimini for interment in a place of honor in the city’s cathedral – an act that did not help his standing with the Church.[137]

Of all of the Quattrocento rulers, Sigismondo was the most obsessed with his image, fame, and legacy; in this respect, he was truly a man of the Renaissance. During the Renaissance, patronage of art was as much a political project as it was a cultural one; Sigismondo was no exception to this rule, as he used his patronage and the iconography he promoted to try to build legitimacy in his court and his dynastic titles.[138] Following the advice of none other than Petrarch, Sigismondo sought to legitimate the reputation he earned through martial means by the use of humanism and patronage which embellished his image as a beneficent, just, strong, courageous, and wise lord; this became part of “a new model of the ruler based on Roman virtù rather than on Christian virtue.”[139] Fame was a major part of Sigismondo’s conception of legitimacy, a sentiment echoed by his court poet Basinio, who said, “Fame is the god of men. It rolls through many mouths and great peoples, is carried to great cities through time, and is reborn in every age.”[140] The fame and glory of Sigismondo’s court would be seen not only as a reflection of the power of Rimini, but would also serve to promote himself in comparison to his peer rulers in the eyes of those greater powers which controlled the political destiny of Italy.[141] Sigismondo habitually distributed the fruits of his humanist patronage, sending fellow rulers copies of literary works from Valturio and Basinio along with medals which promoted and glorified Sigismondo’s image of power.[142] Medals were a bigger part of Sigismondo’s efforts at image-making than they were for most of his peers. His use of the relatively new art of medal-pressing was innovative and would be replicated throughout the centuries; Sigismondo did not only press images of himself onto medals (as seen in Figure 3), he also created medals to commemorate his major architectural works and personal successes.[143] The Malatesta medals were often more straightforward and comprehensible than were the efforts of his peers. He used text, avoided overwrought symbolism, and stuck to relatively simple imagery to convey his message.[144] These medals, many of which are still in good condition over five hundred years later, were meant to carry Sigismondo’s fame through the ages and keep his name alive[145]; clearly this was a successful gambit, not only because the medals survived but also because so many of his peers and later rulers would mimic this method.

Sigismondo created his own image, but also piggybacked off of Rimini’s classical past and the Quattrocento fascination with antiquity and humanism; according to Ettlinger, “more than any other Italian lord of this period, Sigismondo understood how to reuse the past to fashion an image for the future.”[146] One such example of this cooption of the past was in Sigismondo’s self-created genealogy connecting him to one of ancient Rome’s leading figures: Scipio Africanus. Scipio was a scion of the Roman Republic, marrying military skill to republican virtù; his exploits in the ultimate defeat of Hannibal and Carthage in the Second Punic War were legendary and made him a hero at the time and in the millennia since.[147] Scipio was re-popularized by the writings of the famed Italian humanist Petrarch, who penned an unfinished epic to the Roman icon; this made Scipio into somewhat of a cult hero of the courts of Quattrocento rulers, especially those who made their reputations as condottieri.[148] Sigismondo adopted Scipio as an ancestor, tying the ancient’s legitimacy and virtù into his own Renaissance story; this was just another ploy for legitimacy on Malatesta’s part. Perhaps the most lasting and unique appropriations of classical pagan antiquity for the purpose of political image-making and power projection were Sigismondo’s building projects, which “drew together the splendor of the Roman past and the prosperity of the Malatesta present, to display visually the links between himself and his people.”[149]

Figure 4: Tempio Malatestiano, exterior; Leon Battista Alberti, Tempio Malatestiano, circa 1450, marble and stone, unfinished, Rimini, Italy.

Through the course of his career, Sigismondo Malatesta commissioned several building projects, running the gamut from military fortifications like walls and towers to civilian infrastructure including hydraulic engineering.[150] The two most influential architectural works he willed into being were as important for their physical design as they were for their political imagery: the Castel Sismondo and the Tempio Malatestiano. Both of these buildings were meant to glorify the Malatesta family, project Sigismondo’s power, and build on his legitimacy as a good and just ruler of Rimini.[151] The Castel Sismondo, rebuilt by Sigismondo between 1437 and 1444, was both a military fortress as well as the site of one of the Renaissance’s most fascinating courts.[152] The castle, named after the Holy Roman Emperor Sigismund who knighted Sigismondo and his brother in 1433, was a masonry representation of Malatesta power and legitimacy – hence its imperial associations. The fortress was a marvel of Quattrocento military engineering, with sloped walls, a polygonal design, and a wide and deep moat; these characteristics were expressly meant to put a stop to the artillery barrages that – as Sigismondo well knew – were devastating more traditional Medieval castles all across Italy.[153] Much of what was written at the time about the Castel Sismondo was praise for its innovative military design, but just as important was Sigismondo’s total reorientation of the city of Rimini around his newly remodeled court. Although the castle already existed within the cityscape of Rimini, Sigismondo chose to destroy several blocks worth of buildings – including a convent and the bishop’s residence – around it so as to create an open forecourt linking the city with the fortress.[154] This clearing process completely changed the landscape of Rimini, orienting the entire city around the powerful, unassailable position of the Malatestas; this was part and parcel of Sigismondo’s projection of an image of independence, justice, and legitimacy to his subjects.[155] The new piazza in front of the Castel Sismondo was used by the citizens of Rimini for festivals, markets, and other civic events, further imbuing the Malatesta dynasty into the urban fabric.[156] According to Ettlinger, “To achieve his purpose of establishing a new center testifying to the hereditary right of the Malatesta to rule, Sigismondo created not just a residence but an extended complex that would link the authority and potency of the Malatesta and the city of Rimini irrevocably in the minds of his subjects and peers.”[157]

Although the Castel Sismondo was the focal point for Malatesta governance and defense of Rimini, a much smaller building would be far more influential in later architecture and would come to define the image of Sigismondo Malatesta as a pagan prince: the Tempio Malatestiano (Figure 4). The longstanding Church of San Francesco in Rimini was transformed by Sigismondo’s vision into a classical temple replete with pagan iconography, classical imagery, and antiquity-inspired inscriptions.[158] The church, which served as a Malatesta burial site for generations, was recreated as a shrine to the mystique, power, and legitimacy of the dynasty; this overhaul “brought San Francesco onto the stage of the theater of state that Sigismondo had begun to construct with Castel Sismondo a decade earlier.”[159] The renovation was one of the major complaints of Pius II in his reverse canonization and excommunication of the Lord of Rimini, as he stated that the church was filled “so full of pagan works of art that it seemed less a Christian sanctuary than a temple of heathen devil-worshippers.”[160] The façade of the Tempio was designed in conjunction with Leon Battista Alberti, one of the leading architects of the day and the exemplar of the Florentine style so deeply associated with the Renaissance; it was the first serious attempt at a recreation of a Greco-Roman structure in the Quattrocento and served as the launching point for the coming classical revival.[161] The outside of the Tempio, seen in Figure 4 in the Appendix, is a masterpiece of classical inspiration. It has large arches which deliberately evoke the Arch of Augustus Rimini was famed for, inscriptions in period-accurate Roman script, and was built with marble that would not have been out of place in ancient Rome; if one could not see the older church structure underneath, it would look as though the building was indeed a relic of some ancient past.

Although the interior of the church was not altered in form, it was certainly revamped in substance and style; the use of imagery widely considered pagan would come to define the Tempio and Sigismondo himself. More modern interpretations of the iconography of the Tempio dispute the outright pagan explanation and instead focus on the imagery as a means of keeping the memory of the Malatesta family alive through the centuries, with an explicit emphasis on the dynasty’s legitimacy and just rulership.[162] In this way, the Tempio is a further embodiment of Sigismondo’s lifelong quest for acceptance and authority. The interior of the Tempio consisted of several separate chapels, each of which had a theme that blended Christianity, classical antiquity, and secular power; images of the sun, the muses of liberal arts, and the planets sat side-by-side in groupings that could be interpreted as Christian or pagan, depending on the viewer.[163] The iconography of the sun could represent Justice or Christ[164], the planets recalled both the pagan gods and the passage of time[165], and the muses of liberal arts spoke to Sigismondo’s cultural and intellectual patronage. Two specific examples of the imagery of legitimacy, both of which reference the Holy Roman Emperor Sigismund, are useful to detail further. The first is quite possibly the most important artwork in the entire Tempio: a fresco of Sigismondo Malatesta kneeling before St. Sigismund painted by the renowned Piero della Francesca. This image is simultaneously Christian and secular, as the features of the saint reference the features of the Emperor Sigismund, who shared his name.[166] The fact that Sigismondo Malatesta is represented as kneeling before the saint reinforces the claim that the Holy Roman Emperor was his overlord and the fount of his legitimacy; the fresco has been interpreted as “an expression of Sigismondo’s hopes for a noble title and a ‘perpetual inheritance’.”[167] The second representation also related to Saint Sigismund, who appears in the chapel of Sigismondo Malatesta as the personification of Justice.[168] He is not depicted keeping guard over Sigismondo’s own chapel, but instead gazes across the aisle to the Chapel of the Ancestors, where the prior generations of the Malatesta line are buried.[169] This is meant as an explicitly political message, linking all generations of Malatesta to the concept of Justice, the most important aspect of legitimate and good rule.[170] In this one building, secular and religious imagery interacted and reinforced one another, all serving the ultimate purpose of glorifying the Malatestas and proving their legitimate claim to rule Rimini by right.[171]


Tyranny was not as simple a concept in Quattrocento Italy as it seems to be today. As we have seen, many different factors and models were used to differentiate tyrants from just rulers, some of which were actually contradictory. Thinkers of the Renaissance used legal, moral, and cultural frameworks to understand and interrogate the idea of tyranny, as well as to apply it in the real world. Each of these factors mattered when it came to tyranny, although the theorists of the Renaissance did not agree on their relative importance or even what side of the coin to be on. From the ideas of Coluccio Salutati and Bartolus of Sassoferrato in the fourteenth century to the theories of Niccolò Machiavelli in the sixteenth century, views of just rule evolved and shifted over time, even if the base aspects of legitimacy were unchanging. The Quattrocento specifically is a great prism through which to question the basic assumptions and characteristics of tyranny and just rule, as it was the apex of the small Italian city-state ruled by a condottiere lord; after this the influence of smaller statelets subsided with the increasing power of the Pope, the Holy Roman Empire, Spain, and France within the Italian Peninsula. The Quattrocento was indeed the age of the petty despot, and the last time this governing model would reign supreme in Italy. The intrinsic complexity of the era and the men who lived and ruled during it can be lost when taking a brief glance at their biographies or even the contemporary representations of them. If one was to take the most popular primary sources at face value, Federico da Montefeltro would emerge as a perfect duke, while Sigismondo Malatesta would be reviled as the epitome of evil and heresy. As we know from the investigation above, the reality is far more nuanced than the myth. Montefeltro had issues with his own legitimacy, had a mean streak himself, and patronized arts for the sake of political power and imagery; Malatesta was a military genius, was not the monster he was depicted as by Pius, and embraced the culture of antiquity without abandoning Christianity completely. Both of these men embodied aspects of good rule, as well as aspects of tyranny; their biggest issue was also the most important factor of the politics of the Quattrocento – legitimacy. Montefeltro would likely be seen by Bartolus and Salutati as a better, more just ruler than Malatesta, whereas this would be reversed in the mind of Machiavelli, who would have seen Sigismondo as the ultimate representative of his political theories as laid out in The Prince. It is clear that the lives of these men – cultural, moral, and legal – did not fall into black-and-white, Manichaean categories. Each tried his best to provide a stable legacy for his dynasty and to embody the concept of the just ruler, even though they took wildly divergent paths to reach their objectives. Categorizing these rulers into simple groups of ‘tyrant’ and ‘not tyrant’ is impossible if one is to be faithful to the history. Machiavelli himself had this right, as he does not once use the word ‘tyrant’ in The Prince, instead opting for ‘new prince’, a far more neutral term. This is a useful message for us to remember in the modern day, as the temptation towards Manichaean thinking is strong; we would do far better to illuminate issues through nuance than obscure them through overly simplistic thinking. In that, we would truly be continuing the project of the Renaissance humanists.


Alberti, Leon Battista. Tempio Malatestiano. Circa 1450. Marble and stone, unfinished. Rimini, Italy.

Alexander, Jonathan J.G. “’Perfection of Illustration and Ornament’.” In Federico da Montefeltro and His Library, edited by Marcello Simonetta, 15-17. Milan: Y.Press SRL, 2007.

Bartolus of Sassoferrato. “De Tyrannia.” In Humanism and Tyranny, translated and edited by Ephraim Emerton, 126-154. Cambridge, Massachusetts: Harvard University Press, 1925.

Berruguete, Pedro. Portrait of Federico da Montefeltro and His Son Guidobaldo. 1476. Tempera on wood, 138.5 cm x 82.5 cm (54.5 in x 32.5 in). Galleria Nazionale delle Marche, Urbino, Italy.

Burckhardt, Jacob. Civilization of the Renaissance in Italy. Translated by S.G.C. Middlemore (1878). Kitchener, Ontario, Canada: Batoche Books, 2001.

Castiglione, Baldassare. The Book of the Courtier. Translated and edited by Friench Simpson. New York: Frederick Ungar Publishing, 1964.

D’Elia, Anthony F. Pagan Virtue in a Christian World. Cambridge, Massachusetts: Harvard University Press, 2016. E-Book.

Da Bisticci, Vespasiano. “Federigo, Duke of Urbino (1422-1482).” In The Vespasiano Memoirs: Lives of the Illustrious Men of the XVth Century, translated by William George and Emily Waters, 83-114. Toronto: University of Toronto Press in association with the Renaissance Society of America, 1997.

Da Montefeltro, Federico. “Letter Patent to Master Luciano Laurana.” In The Renaissance in Europe: An Anthology, edited by Peter Elmer, Nick Webb and Roberta Wood, 204-206. New Haven, Connecticut: Yale University Press, 2000.

De’Pasti, Matteo. Medal: Bust of Sigismondo Pandolfo Malatesta. Circa 1447 (model). Copper alloy, 8.4 cm diameter x 294.21 g weight (3.3 in diameter x 10.38 oz weight). Metropolitan Museum of Art, New York City, USA.

Deiss, Joseph Jay. Captains of Fortune: Profiles of Six Italian Condottieri. New York: Thomas Y. Crowell Company, 1967.

Della Francesca, Piero. Portraits of the Duke and Duchess of Urbino, Federico da Montefeltro and Battista Sforza. 1470. Tempera on wood, 47 cm x 33 cm (18.5 in x 12.9 in). Uffizi Gallery, Florence, Italy.

Ettlinger, Helen Shahrokh. “The Image of a Renaissance Prince: Sigismondo Malatesta and the Arts of Power.” PhD dissertation, University of California Berkeley, 1988.

Fenucci, Fabrizio. “Notes on Federico da Montefeltro’s Emblems.” In Federico da Montefeltro and His Library, edited by Marcello Simonetta, 81-87. Milan: Y.Press SRL, 2007.

Larner, John. The Lords of Romagna: Romagnol Society and the Origins of the Signorie. Ithaca, New York: Cornell University Press, 1965.

Machiavelli, Niccolò. “The Discourses.” In The Renaissance in Europe: An Anthology, edited by Peter Elmer, Nick Webb and Roberta Wood, 139-148. New Haven, Connecticut: Yale University Press, 2000.

Machiavelli, Niccolò. The Prince. Translated by W.K. Marriott. New York: Fall River Press, 2017.

Mallett, Michael. Mercenaries and Their Masters: Warfare in Renaissance Italy. London: The Bodley Head Ltd., 1974.

Pernis, Maria Grazia, and Laurie Schneider Adams. Federico da Montefeltro & Sigismondo Malatesta: The Eagle and the Elephant. New York: Peter Lang Publishing, 1996.

Peruzzi, Marcella. “The Library of Glorious Memory: History of the Montefeltro Collection.” In Federico da Montefeltro and His Library, edited by Marcello Simonetta, 29-40. Milan: Y.Press SRL, 2007.

Salutati, Coluccio. “De Tyranno.” In Humanism and Tyranny, translated and edited by Ephraim Emerton, 70-116. Cambridge, Massachusetts: Harvard University Press, 1925.

Simonetta, Marcello. “Federico da Montefeltro: The Self-Portrait of a Renaissance Man.” In Federico da Montefeltro and His Library, edited by Marcello Simonetta, 18-28. Milan: Y.Press SRL, 2007.

Trease, Geoffrey. The Condottieri: Soldiers of Fortune. New York: Holt, Rinehart and Winston, 1971.

[1] Jacob Burckhardt, Civilization of the Renaissance in Italy, trans. S.G.C. Middlemore (Kitchener, Ontario, Canada: Batoche Books, 2001), 6.

[2] Michael Mallett, Mercenaries and Their Masters: Warfare in Renaissance Italy (London: The Bodley Head Ltd., 1974), 79-80.

[3] John Larner, The Lords of Romagna: Romagnol Society and the Origins of the Signorie (Ithaca, New York: Cornell University Press, 1965), 43.

[4] Larner, The Lords of Romagna, 44.

[5] Larner, The Lords of Romagna, 57.

[6] Larner, The Lords of Romagna, 77.

[7] Coluccio Salutati, “De Tyranno,” in Humanism and Tyranny, trans. and ed. Ephraim Emerton (Cambridge, Massachusetts: Harvard University Press, 1925), 94.

[8] Salutati, “De Tyranno,” 94.

[9] Salutati, “De Tyranno,” 94.

[10] Niccolò Machiavelli, “The Discourses,” in The Renaissance in Europe: An Anthology, ed. Peter Elmer, Nick Webb and Roberta Wood (New Haven, Connecticut: Yale University Press, 2000), 140.

[11] Machiavelli, “The Discourses,” 141.

[12] Bartolus of Sassoferrato, “De Tyrannia,” in Humanism and Tyranny, trans. and ed. Ephraim Emerton (Cambridge, Massachusetts: Harvard University Press, 1925), 126.

[13] Salutati, “De Tyranno,” 76.

[14] Bartolus, “De Tyrannia,” 127.

[15] Bartolus, “De Tyrannia,” 130-131.

[16] Salutati, “De Tyranno,” 78.

[17] Bartolus, “De Tyrannia,” 132.

[18] Bartolus, “De Tyrannia,” 132.

[19] Bartolus, “De Tyrannia,” 132.

[20] Bartolus, “De Tyrannia,” 133.

[21] Salutati, “De Tyranno,” 99.

[22] Salutati, “De Tyranno,” 100.

[23] Bartolus, “De Tyrannia,” 129.

[24] Bartolus, “De Tyrannia,” 140.

[25] Bartolus, “De Tyrannia,” 142-144.

[26] Machiavelli, “The Discourses,” 143.

[27] Machiavelli, “The Discourses,” 143.

[28] Niccolò Machiavelli, The Prince, trans. W.K. Marriott (New York: Fall River Press, 2017), 64.

[29] Machiavelli, The Prince, 65.

[30] Machiavelli, The Prince, 77.

[31] Machiavelli, The Prince, 80.

[32] Machiavelli, The Prince, 73.

[33] Salutati, “De Tyranno,” 78.

[34] Baldassare Castiglione, The Book of the Courtier, trans. and ed. Friench Simpson (New York: Frederick Ungar Publishing, 1964), 2-3.

[35] Maria Grazia Pernis and Laurie Schneider Adams, Federico da Montefeltro & Sigismondo Malatesta: The Eagle and the Elephant (New York: Peter Lang Publishing, 1996), 14-15.

[36] Pernis, The Eagle and the Elephant, 24-25.

[37] Pernis, The Eagle and the Elephant, 25.

[38] Geoffrey Trease, The Condottieri: Soldiers of Fortune (New York: Holt, Rinehart and Winston, 1971), 310.

[39] Pernis, The Eagle and the Elephant, 25.

[40] Vespasiano da Bisticci, “Federigo, Duke of Urbino (1422-1482),” in The Vespasiano Memoirs: Lives of the Illustrious Men of the XVth Century, trans. William George and Emily Waters (Toronto: University of Toronto Press in assoc. with the Renaissance Society of America, 1997), 107.

[41] Vespasiano, “Federigo, Duke of Urbino,” 108-109.

[42] Vespasiano, “Federigo, Duke of Urbino,” 108.

[43] Vespasiano, “Federigo, Duke of Urbino,” 108.

[44] Trease, The Condottieri, 314-315.

[45] Trease, The Condottieri, 315.

[46] Vespasiano, “Federigo, Duke of Urbino,” 95-96.

[47] Marcello Simonetta, “Federico da Montefeltro: The Self-Portrait of a Renaissance Man,” in Federico da Montefeltro and His Library, ed. Marcello Simonetta (Milan: Y.Press SRL, 2007), 21.

[48] Trease, The Condottieri, 316.

[49] Simonetta, “The Self-Portrait of a Renaissance Man,” 22.

[50] Trease, The Condottieri, 316-317.

[51] Fabrizio Fenucci, “Notes on Federico da Montefeltro’s Emblems,” in Federico da Montefeltro and His Library, ed. Marcello Simonetta (Milan: Y.Press SRL, 2007), 81-86.

[52] Trease, The Condottieri, 316.

[53] Simonetta, “The Self-Portrait of a Renaissance Man,” 24.

[54] Simonetta, “The Self-Portrait of a Renaissance Man,” 24.

[55] Trease, The Condottieri, 316-317.

[56] Pernis, The Eagle and the Elephant, 34-35.

[57] Vespasiano, “Federigo, Duke of Urbino,” 91-92.

[58] Jonathan J.G. Alexander, “’Perfection of Illustration and Ornament’,” in Federico da Montefeltro and His Library, ed. Marcello Simonetta (Milan: Y.Press SRL, 2007), 16.

[59] Pernis, The Eagle and the Elephant, 20.

[60] Pernis, The Eagle and the Elephant, 67-68.

[61] Pernis, The Eagle and the Elephant, 68.

[62] Alexander, “’Perfection of Illustration and Ornament’,” 16.

[63] Castiglione, The Book of the Courtier, 3.

[64] Federico da Montefeltro, “Letter Patent to Master Luciano Laurana,” in The Renaissance in Europe: An Anthology, ed. Peter Elmer, Nick Webb and Roberta Wood (New Haven, Connecticut: Yale University Press, 2000), 204-206.

[65] Pernis, The Eagle and the Elephant, 60.

[66] Pernis, The Eagle and the Elephant, 60-61.

[67] Pernis, The Eagle and the Elephant, 69.

[68] Vespasiano, “Federigo, Duke of Urbino,” 102.

[69] Marcella Peruzzi, “The Library of Glorious Memory: History of the Montefeltro Collection,” in Federico da Montefeltro and His Library, ed. Marcello Simonetta (Milan: Y.Press SRL, 2007), 32-33.

[70] Peruzzi, “History of the Montefeltro Collection,” 35.

[71] Peruzzi, “History of the Montefeltro Collection,” 38.

[72] Vespasiano, “Federigo, Duke of Urbino,” 110.

[73] Anthony F. D’Elia, Pagan Virtue in a Christian World (Cambridge, Massachusetts: Harvard University Press, 2016), 1.

[74] D’Elia, Pagan Virtue in a Christian World, 3-4.

[75] Joseph Jay Deiss, Captains of Fortune: Profiles of Six Italian Condottieri (New York: Thomas Y. Crowell Company, 1967), 197.

[76] D’Elia, Pagan Virtue in a Christian World, 4-5.

[77] Pernis, The Eagle and the Elephant, 9.

[78] Pernis, The Eagle and the Elephant, 9-10.

[79] Pernis, The Eagle and the Elephant, 10-11.

[80] Trease, The Condottieri, 302.

[81] Deiss, Captains of Fortune, 205.

[82] Deiss, Captains of Fortune, 205.

[83] Helen Shahrokh Ettlinger, “The Image of a Renaissance Prince: Sigismondo Malatesta and the Arts of Power” (PhD dissertation, University of California Berkeley, 1988), 22-25.

[84] Ettlinger, “The Image of a Renaissance Prince,” 25.

[85] Ettlinger, “The Image of a Renaissance Prince,” 25.

[86] Ettlinger, “The Image of a Renaissance Prince,” 27.

[87] Ettlinger, “The Image of a Renaissance Prince,” 27.

[88] Ettlinger, “The Image of a Renaissance Prince,” 47.

[89] Ettlinger, “The Image of a Renaissance Prince,” 72.

[90] Pernis, The Eagle and the Elephant, 12.

[91] Ettlinger, “The Image of a Renaissance Prince,” 110.

[92] Deiss, Captains of Fortune, 205.

[93] D’Elia, Pagan Virtue in a Christian World, 123.

[94] Machiavelli, The Prince, 74.

[95] Machiavelli, The Prince, 69-70.

[96] D’Elia, Pagan Virtue in a Christian World, 119.

[97] Deiss, Captains of Fortune, 200-202.

[98] Deiss, Captains of Fortune, 206.

[99] Pernis, The Eagle and the Elephant, 12-13.

[100] Pernis, The Eagle and the Elephant, 12-13.

[101] D’Elia, Pagan Virtue in a Christian World, 188-189.

[102] D’Elia, Pagan Virtue in a Christian World, 189.

[103] Deiss, Captains of Fortune, 213-214.

[104] Burckhardt, The Civilization of the Renaissance in Italy, 31.

[105] D’Elia, Pagan Virtue in a Christian World, 112.

[106] Ettlinger, “The Image of a Renaissance Prince,” 35-36.

[107] D’Elia, Pagan Virtue in a Christian World, 117.

[108] D’Elia, Pagan Virtue in a Christian World, 133-134.

[109] D’Elia, Pagan Virtue in a Christian World, 139-140.

[110] D’Elia, Pagan Virtue in a Christian World, 148.

[111] D’Elia, Pagan Virtue in a Christian World, 7.

[112] Trease, The Condottieri, 302.

[113] Deiss, Captains of Fortune, 208.

[114] Ettlinger, “The Image of a Renaissance Prince,” 50.

[115] Trease, The Condottieri, 311.

[116] Trease, The Condottieri, 311.

[117] Ettlinger, “The Image of a Renaissance Prince,” 36.

[118] Trease, The Condottieri, 311.

[119] Trease, The Condottieri, 311.

[120] D’Elia, Pagan Virtue in a Christian World, 120-121.

[121] D’Elia, Pagan Virtue in a Christian World, 121.

[122] Ettlinger, “The Image of a Renaissance Prince,” 50-51.

[123] Ettlinger, “The Image of a Renaissance Prince,” 51.

[124] D’Elia, Pagan Virtue in a Christian World, 189.

[125] D’Elia, Pagan Virtue in a Christian World, 265.

[126] D’Elia, Pagan Virtue in a Christian World, 265.

[127] D’Elia, Pagan Virtue in a Christian World, 152.

[128] Deiss, Captains of Fortune, 224.

[129] D’Elia, Pagan Virtue in a Christian World, 152.

[130] D’Elia, Pagan Virtue in a Christian World, 28.

[131] D’Elia, Pagan Virtue in a Christian World, 75.

[132] D’Elia, Pagan Virtue in a Christian World, 69.

[133] D’Elia, Pagan Virtue in a Christian World, 78-79.

[134] D’Elia, Pagan Virtue in a Christian World, 226.

[135] Trease, The Condottieri, 312.

[136] Trease, The Condottieri, 314.

[137] Deiss, Captains of Fortune, 237.

[138] Ettlinger, “The Image of a Renaissance Prince,” 18-20.

[139] Ettlinger, “The Image of a Renaissance Prince,” 133-134.

[140] D’Elia, Pagan Virtue in a Christian World, 232-233.

[141] Ettlinger, “The Image of a Renaissance Prince,” 139.

[142] D’Elia, Pagan Virtue in a Christian World, 38.

[143] Ettlinger, “The Image of a Renaissance Prince,” 120.

[144] Ettlinger, “The Image of a Renaissance Prince,” 177.

[145] Ettlinger, “The Image of a Renaissance Prince,” 177.

[146] Ettlinger, “The Image of a Renaissance Prince,” 144.

[147] D’Elia, Pagan Virtue in a Christian World, 70.

[148] D’Elia, Pagan Virtue in a Christian World, 70.

[149] Ettlinger, “The Image of a Renaissance Prince,” 68.

[150] Pernis, The Eagle and the Elephant, 61.

[151] Ettlinger, “The Image of a Renaissance Prince,” 71-73.

[152] D’Elia, Pagan Virtue in a Christian World, 33.

[153] D’Elia, Pagan Virtue in a Christian World, 33-34.

[154] Pernis, The Eagle and the Elephant, 62.

[155] Ettlinger, “The Image of a Renaissance Prince,” 73.

[156] Ettlinger, “The Image of a Renaissance Prince,” 81-82.

[157] Ettlinger, “The Image of a Renaissance Prince,” 82.

[158] Deiss, Captains of Fortune, 218-219.

[159] Ettlinger, “The Image of a Renaissance Prince,” 199-200.

[160] Ettlinger, “The Image of a Renaissance Prince,” 195.

[161] Deiss, Captains of Fortune, 218.

[162] Ettlinger, “The Image of a Renaissance Prince,” 206.

[163] Ettlinger, “The Image of a Renaissance Prince,” 207-217.

[164] Ettlinger, “The Image of a Renaissance Prince,” 235.

[165] Ettlinger, “The Image of a Renaissance Prince,” 210.

[166] Ettlinger, “The Image of a Renaissance Prince,” 209.

[167] Ettlinger, “The Image of a Renaissance Prince,” 209.

[168] Ettlinger, “The Image of a Renaissance Prince,” 234-235.

[169] Ettlinger, “The Image of a Renaissance Prince,” 235.

[170] Ettlinger, “The Image of a Renaissance Prince,” 235.

[171] Ettlinger, “The Image of a Renaissance Prince,” 228.

[172] Piero della Francesca, Portraits of the Duke and Duchess of Urbino, Federico da Montefeltro and Battista Sforza, 1470, tempera on wood, 47 cm x 33 cm (18.5 in x 12.9 in), Uffizi Gallery, Florence, Italy.

[173] Pedro Berruguete, Portrait of Federico da Montefeltro and His Son Guidobaldo, 1476, tempera on wood, 138.5 cm x 82.5 cm (54.5 in x 32.5 in), Galleria Nazionale delle Marche, Urbino, Italy.

[174] Matteo de’Pasti, Medal: Bust of Sigismondo Pandolfo Malatesta, circa 1447 (model), copper alloy, 8.4 cm diameter x 294.21 g weight (3.3 in diameter x 10.38 oz weight), Metropolitan Museum of Art, New York City, USA.

[175]Leon Battista Alberti, Tempio Malatestiano, circa 1450, marble and stone, unfinished, Rimini, Italy.

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