Fortune’s Favours

Discovering Machiavelli’s talent for losing.

Niccolò Machiavelli (detail), by Antonio Maria Crespi Castoldi, 17th century © SZ Photo/Scherl/Bridgeman Images.

In 1516, Niccolò Machiavelli, keen to earn the favour of Florence’s recently restored ruling family, arrived at the Palazzo Medici to present Lorenzo de’ Medici with a copy of The Prince. The occasion did not go to plan. Lorenzo – who had inherited his name from his grandfather, Lorenzo ‘the Magnificent’, but lacked that forebear’s brilliance – was quickly distracted from political theory when another petitioner turned up with a pair of hunting dogs. Alexander Lee’s new biography of Machiavelli has plenty of such colourful anecdote, though he is careful to warn us that the source for this tale may not be entirely reliable. Yet the story illustrates well the Machiavelli he presents: a man with a talent for ending up on the losing side. 

Following the French descent into Italy in 1494 and the expulsion of the Medici that followed, then the brief ascendance of hellfire preacher Girolamo Savonarola, Machiavelli obtained the post of second chancellor of the Florentine Republic. In that capacity, Lee explains, ‘though he had enjoyed some modest successes, they were far outweighed by his many failures’. He was a decent administrator, but not an outstanding one. The outcomes of his diplomatic missions were far from universally impressive. He was no doubt fun to have around for the office banter: the chancellery’s work ethic was relaxed enough to allow for gambling on the job, while Machiavelli’s assistant was apparently the subject of an office crush. (Lee, to his credit, has no time for coyness about the same-sex affairs that flourished in Florentine society.) There was, however, serious business to be done, and Machiavelli’s principal achievement in the first decade of the 16th century was the establishment of a citizen militia in Florence, though even this proved a poisoned chalice, for it was feared it might become a weapon of tyranny. In the meantime, he played a key role in the republic’s negotiations with Cesare Borgia, dealt with endless factional squabbles in the subject town of Pistoia and oversaw a disastrous attempt to divert the River Arno as a means of winning a war with Pisa. The reflections that he penned on such tasks would inform his later and better-known works. 

Machiavelli’s association with the republican regime, however, did him no favours when in 1512, after 18 years of exile, the Medici secured their return to Florence thanks to an alliance with the Spanish. There were, inevitably, questions about his loyalty; he was imprisoned and tortured, but after the surprise election of Giovanni de’ Medici as Pope Leo X in March 1513 the new rulers could afford to be generous and Machiavelli was among the prisoners freed. While it might be fun to imagine that Machiavelli’s versifying for Giuliano de’ Medici got him out of jail, Lee, duly cautious, suggests that that is not, in fact, true. Machiavelli retreated to the pastoral setting of his family home in Sant’Andrea in Percussina, just south of Florence, where he began to write his most celebrated works. Lee lyrically conveys the beauty of the setting: the ‘swaying cypress trees’, the ‘ground carpeted with mushrooms’ and the ‘wild boar … snuffling among the bracken’. 

Slowly, over the next few years, and with the help of influential friends, Machiavelli made his way into the favour of the new rulers and, in 1520, finally obtained a prestigious commission to write a history of Florence. All might have ended happily there, but in 1527 the Medici were once again forced into exile. Machiavelli, who died two months later, did not see their return, nor the trauma and misery of the siege that made it happen. That hallmark of his work, Fortune, shined upon him only posthumously.

The posthumous reputation of Machiavelli is not, however, Lee’s focus here. There is none of the ‘Machiavel’ of Shakespeare, still less the variously Machiavellian characters of modern popular culture. Machiavelli is firmly grounded in its subject’s present-day experience, as Lee follows him through the twists and turns of decades of conflict. One imagines it was an exhausting process for those involved and it is occasionally exhausting for the reader, too, but on the other hand it delivers the detailed historical context for each of Machiavelli’s projects in a way that a broader brush or more creative literary biography would not. 

Though this is primarily a synthesis of existing studies and published documents, Lee also has clear preferences when it comes to interpretation, making the case for a much more straightforward reading of Machiavelli’s work than, for example, Erica Benner with her emphasis on irony. Inevitably, there is more attention here to some contexts than to others. Early on we hear of treatments for the plague; later we find Machiavelli consulting an astrologer, perhaps the best of all settings for a chat about Fortune; but the overall emphasis is on politics and diplomacy. The geographical scope is primarily Florentine: we journey out of the city when Machiavelli does, but not a great deal otherwise. Readers will have to remind themselves that the ‘not particularly religious’ Machiavelli shared a continent with Martin Luther. 

It remains a challenge, moreover, for Lee to translate the variety of innovation in Machiavelli scholarship into a chronological narrative. The academic literature is primarily thematic: it explores Machiavelli and gender, or the concept of redemption in Machiavelli, or the details of language in his works. There are certainly echoes of that here. Between the entertaining discussion of Machiavelli’s sex life (there are mistresses and rent boys aplenty) and the manly concept of virtù there is an intriguing take on masculinity trying to get out, for example, but the narrative form doesn’t quite allow it space. Still, the great strength of this book is that it raises such questions in the minds of readers – and provides a stylish and impressively researched introduction to Machiavelli’s times for those new to his world. 

Machiavelli: His Life and Times
Alexander Lee
Picador 768pp £30


Catherine Fletcher is the author of The Beauty and the Terror: an Alternative History of the Italian Renaissance (Bodley Head, 2020).


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