Renaissance Men: Cesare Borgia & Pope Alexander VI.
This father-son partnership briefly created one of Renaissance Italy’s most magnificent demonstrations of Machiavellian power-wielding — as documented by Machiavelli himself.
Two books you’re certain to find in the libraries of Type A corporate power-mongers are Sun Tzu’s The Art of War (“Appear weak when you are strong, and strong when you are weak”) and Niccolò Machiavelli’s The Prince (“Never attempt to win by force what can be won by deception”).
Portrait of Niccolò Machiavelli (1469-1527) by Santi di Tito
The latter master manipulator — an Italian Renaissance-era diplomat, historian, politician, philosopher and author, whose name has come to be synonymous with ruthless scheming — devotes a significant portion of his best-known work to examining the rise and fall of a contemporary he much admired, Cesare Borgia.
Cesare was the bastard (perhaps in both senses of the word) son of Pope Alexander VI and his longterm mistress, Roman aristocrat Vanozza Dei Cattanei. Born into a wealthy, well-connected family in Valencia in 1431, the future pope rose rapidly through church ranks following his uncle’s elevation to the papacy in 1455, eventually taking the top job himself in 1492. As one might gather from Pope Alexander’s fatherhood of Cesare — one of at least nine children he sired with various mistresses — the pontiff approached his vows of chastity rather casually. As for the vow of poverty… Said to be lacking almost entirely in religious sentiment, Pope Alexander made no bones about seeing his office primarily as a means of increasing the Borgia family’s power, wealth and holdings. Which he did with gusto.
His eldest son Cesare (who, along with his three other children by Vanozza — Giovanni, Lucrezia and Gioffre — he legitimised after taking the papacy) was the primary tool Pope Alexander used to achieve his worldly ends. Cesare was first groomed to be Alexander’s successor in the church, but when military-focused younger son Giovanni was murdered — stabbed nine times, his throat cut, his body tossed in the Tiber, very likely as the result of quarelling with Cesare over a shared mistress — in 1498, Alexander freed Cesare from his religious vows (he’d been made a bishop at 15 and a cardinal at 18 — meritocracy excelsior) and gave him command of the papal armies.
In partnership with his father, utilising a mix of strategic military might, ‘gunboat’ diplomacy, papal dictates, assassination, and a handy alliance with the French (he’d married into their royal family), Cesare swiftly carved out a vast dukedom for himself in Romagna, northern Italy. According to Machiavelli, Cesare’s methods of seizing and running his new lands were flawless. “I wouldn’t know what better advice to give a ruler new to power than to follow his example,” he wrote.
Altobello Melone’s portrait of Cesare Borgia, circa 1513, which is today displayed at the Accademia Carrara in Bergamo.
Cesare’s Machiavellian playbook: First, wipe out your opponents (in this case, countless pesky bishops, nobles and landowners resistant to ceding power, who were violently dispatched by Borgia henchmen) and win the fealty of their supporters. Next, unleash cruel, draconian rule on your new subjects — via a puppet functionary, who can be executed as a scapegoat when convenient, demonstrating how just, noble, and ruthless you are. Then, ease up and allow a good degree of self-rule. Make ’em love you… While ensuring they continue to fear you, for as Machiavelli put it, “it is much safer to be feared than loved (because) love is preserved by the link of obligation which, owing to the baseness of men, is broken at every opportunity for their advantage; but fear preserves you by a dread of punishment which never fails.”
Many of Cesare’s new subjects actually found him a much better, fairer ruler than those he’d deposed. Machiavelli constantly holds up Cesare as a sterling example of a ‘good ruler’ — albeit, one who was utterly prepared to go bad when need be. An essential trait, according to Machiavelli, since “any man who tries to be good all the time is bound to come to ruin among the great number who are not good. Hence a prince who wants to keep his authority must learn how not to be good, and use that knowledge, or refrain from using it, as necessity requires.”
Jacopo Pesaro presented to St. Peter by Pope Alexander VI, painted by Titian around 1503.
Like his libidinous dad, Cesare knew how to be very, very bad indeed. The Borgia name was a byword for libertinism and licentiousness, as this account of the notorious ‘Banquet of Chestnuts’, from the diary of the Papal Master of Ceremonies, Johannes Burchard, attests: “On Sunday evening, Don Cesare Borgia gave a supper in his apartments in the apostolic palace, with fifty decent prostitutes or courtesans in attendance, who, after the meal, danced… first fully dressed and then naked… The Pope, Don Cesare and Donna Lucrezia were all present to watch. Finally, prizes were offered — silken doublets, pairs of shoes, hats and other garments — for those men who could perform the act most frequently with the prostitutes.”
Though not always in the Vatican’s hallways, Cesare got to know many a woman in the biblical sense. He sired at least 11 illegitimate children, and as if further evidence of his carnal adventurousness were needed, wore it across his face — in the form of hideous syphilis scarring, which necessitated Cesare sporting a mask in public during later life.
Portrait of Pope Alexander VI Cristofano dell'Altissimo, a copy commissioned by Cosimo I de' Medici in 1552.
This swordsman lived by the sword, and died by the sword — although his downfall was equally the result of an overreliance on the support of a powerful backer (his father) which when withdrawn, upon Pope Alexander VI’s death in 1503 and the ascension of a Borgia enemy to the papacy, crippled Cesare’s ability to rule. A series of betrayals, imprisonment, outmaneuverings and defeats soon befell Cesare, who in 1507 finally made the fatal mistake of pursuing, alone, a small group of retreating soldiers who’d been besieging his castle. The knights attacked and killed Borgia, stripped him of his finery and left his corpse lying bloody and naked, save for a tile protecting his modesty.
Though Machiavelli used the example of Cesare’s fall as a cautionary tale, his overall appraisal of Borgia — who’d died aged 31, after less than a decade in power — was overwhelmingly positive. “There was one man,” he wrote of Cesare, “who showed glimpses of greatness, the kind of thing that made you think he was sent by God for the country’s redemption.” Meanwhile, of the father, randy Pope Alexander VI, Machiavelli said, “more than any other pope in history (he) showed what could be done with finance and force of arms”. Indeed, Borgia Sr left the church in a stronger position than ever, its lands, holdings and power exponentially increased, its administration far more effective, and was described by two of his successors, Sixtus V and Urban VIII, as among the finest popes since St. Peter.
Machiavelli was spot on, it seems — sometimes, it takes someone very bad to achieve something very good.
This article first appeared in The Rake magazine in 2016.