On this date in 1499, Florence decapitated its chief general for dereliction of command.
Paolo Vitelli, a noted condottiero whose family had taken over Citta di Castello, was hired by the post-Savonarola Florentine Republic during the Italian Wars to campaign against Florence’s traditional rival, Pisa.
“If this man had taken Pisa, nobody can deny that it would have been proper for the Florentines to keep in with him,” mused Machiavelli years later in The Prince. “For if he became the soldier of their enemies they had no means of resisting, and if they held to him they must obey him.”
The prospective kingpin made fantastic progress against the Pisans, and when news reached his Florentine patrons that Vitelli had taken a key gate in Pisa’s walls, the city smugly began drawing up wishlists of humiliations to heap upon the vanquished. But at the critical moment, “just when the whole army, and especially the youthful Florentines who had joined the camp as volunteers, were carrying all before them by their indomitable ardour, they were suddenly ordered to retreat. And Paolo Vitelli, seeing the unwillingness of the soldiers to obey, rushed among them with his brother Vitellozzo* and drove them back with blows.”
As jaws hit tables all around Florence, Pisa’s defenders were hurriedly patching the breach and retrenching. The attackers had ransacked their treasury to finance the expedition; there was nothing for a do-over. Had Vitelli quailed, or was he playing some double game? Either way, Machiavelli lamented — contemporaneously this time, in his capacity as an emissary of state — “We should have preferred defeat to inaction at so decisive a moment.”
With mingled urgency and circumspection, Florence’s leaders arranged to invite Vitteli to a war council at which he was arrested. Interrogated on September 30th, he was beheaded the very next day.
* Three years later, Paolo’s brother Vitellozzo would also achieve the pages of Executed Today … and once again did so under the sharp eyes of Machiavelli.