Machiavelli was not especially known for his poetry, and few would have called him a man with a claim to Medici support. His family was distinguished but far from rich, and had definite republican associations. Two of his father’s cousins had been beheaded for their opposition to the dynasty’s founder, Cosimo de’ Medici, who had effectively brought the historic republic to an end, in 1434, the better to protect the family bank’s enormous fortune. During Machiavelli’s youth, his father seems to have gained him entrée to the scholarly circles around the widely beloved Lorenzo de’ Medici, who had managed to rule Florence for decades without the Florentines’ feeling the brunt or shame of being ruled. But Lorenzo had died in 1492, and, two years later, the Medici were thrown out of the city. Machiavelli was twenty-five; Giuliano de’ Medici, Lorenzo’s youngest son, was fifteen. While Machiavelli had nothing to do with the religious regime of the Dominican preacher Savonarola, who replaced the Medici—he disdained the preacher’s pious “lies” even while admiring his republican reforms—he came into his own once the city turned against its savior and Savonarola (after suffering fourteen drops of the strappado) was hanged. In 1498, when both God and Savonarola’s supporters lost their government posts, Machiavelli found himself with a job. For the next fourteen years, he proudly served an independent city-state that had returned to its republican form, but was now carefully buttressed to withstand Medici forces lurking at its borders, or the threat that other wealthy families might pose. The chief safeguard of the city’s liberty was the Great Council: an administrative body with a membership of more than three thousand citizens, which gave Florence, with a population of some fifty thousand, the most broadly representative government of its time.

At the age of twenty-nine, Machiavelli was appointed Second Chancellor, with responsibilities for the city’s correspondence and domestic reports. His immense physical and intellectual energy (he casually boasted of making “Greek, Latin, Hebraic, and Chaldean” references) seems to account for his additional appointment, within a month, as Secretary of the so-called Ten of War, which sent him on remote diplomatic missions, usually in the face of impending crisis. War was never far off. These were years when France, Spain, and the Holy Roman Empire, battling over rival claims, sent their formidable armies marching across the weak and continually sparring Italian states; Milan, Genoa, Florence, Venice, Naples, and any number of smaller duchies, marquisates, and republics found it hard to defend themselves, for lack of a united front.

To make matters worse, the varied Italian powers relied on mercenary troops that traded sides more easily than today’s big-league ballplayers, signing a new contract as soon as a better offer came along. Machiavelli thrived on the urgency and the uproar, filling his saddlebags with books and galloping off to argue the Florentine case, then report back on what he had found. In one report, he described his duties as weighing what the ruler’s “intentions are, what he really wants, which way his mind is turning, and what might make him move ahead or draw back”; he wrote of the need “to conjecture the future through negotiations and incidents.” All in all, it seems that he was expected to bring the gifts of a psychologist to the task of a prophet.

He did it very well. Although his lack of wealth kept him from achieving the rank of ambassador—officially a mere envoy, he styled himself, rather grandly, the Florentine Secretary—his unblinking judgments made him the right-hand man of the republic’s chief official, Piero Soderini. He was set to work at the courts of King Louis XII of France, Pope Julius II, and the Holy Roman Emperor Maximilian, all the while studying the differing forms of government and temperament offered to his view. Like most psychologists, Machiavelli was insatiably curious about the human mind. And no one he met impressed him more than Cesare Borgia, the son of the Spanish Pope Alexander VI, who was at the height of his power when, in 1502, he received Machiavelli in the ducal palace of Urbino—by candlelight, as legend has it, dressed all in black, already a figure of self-consciously theatrical menace. Borgia had recently conquered Urbino, along with a large swath of central Italy, by means of daring, speed, and treachery. (Machiavelli especially admired a maneuver in which Borgia had asked the Duke of Urbino to lend him his artillery to help take a nearby town, then turned on the undefended duchy and took it instead.) Machiavelli could not help but contrast Borgia’s stunning effectiveness with the frustratingly slow and prudent Florentine republic, which displayed the deficiencies as well as the virtues of the need for popular consensus, and he wrote excitedly to his bosses in the Palazzo della Signoria of the lessons offered by this majestic enemy. In the ruthless young warrior he saw a potential hero: a leader strong enough to expel the foreign armies and transform Italy from a poetic entity into a real one.