Clement VII

Giulio de' Medici was born weeks after his father's murder in the Pazzi conspiracy, raised by his uncle Lorenzo, and served brilliantly as the power behind his cousin Leo X's throne. Contemporaries agreed he was intelligent, hardworking, and personally upright, and then watched those virtues dissolve in the papacy's hardest decade. His instinct was to weigh every option until events chose for him. Trapped between Emperor Charles V and Francis I of France, he switched alliances at precisely the wrong moments, and in May 1527 the emperor's unpaid army stormed Rome and sacked it for months while Clement watched from Castel Sant'Angelo, escaping later in disguise. The catastrophe broke the Renaissance papacy's confidence and left Clement, thereafter, effectively the emperor's chaplain.

That dependence decided the era's other disaster. When Henry VIII sought an annulment of his marriage to Catherine of Aragon, the emperor's aunt, Clement could neither grant it nor refuse it outright; he delayed, revoked the case to Rome, and watched England legislate itself out of his obedience by 1534. He was not idle otherwise: he commissioned Michelangelo's Last Judgment and the Medici Chapel, patronized Cellini and Machiavelli, refounded Medici rule in Florence, and crowned Charles V at Bologna in 1530, the last imperial coronation a pope ever performed. But the ledger is what it is: on his watch the papacy lost a city to soldiers and a kingdom to lawyers. Even his death in 1534 drew mockery about the death cap mushroom, though illness, not poison, is the documented cause. History's kindest verdict is Guicciardini's: a great cardinal, and a small pope.