Cesare Borgia, son of Pope Alexander VI. With his father’s
support, Borgia was carving out a new state for himself
on the northern borders of the Papal States and had just
captured the city of Urbino to the east of Florence. Sent
on a mission to dissuade Borgia from advancing into Flor-
entine territory, Machiavelli was deeply impressed by the
man. Seductive, determined, cunning and ruthless, Borgia
was a leader in the epic mode. Certainly he could hardly
have been more different from the diplomat’s dithering
boss, Soderini.
Machiavelli was on another mission to Borgia in January
1503 when the adventurer invited a group of rebels to nego-
tiations in the coastal town of Senigallia, then had them
seized and murdered as soon as they were inside the town
walls. Here was a man, Machiavelli realized, determined
to take circumstance by the scruff of the neck. It was not
so much Borgia’s willingness to ignore Christian principles
that fascinated him, as his ability to assess a situation rap-
idly, make his calculations, then act decisively in whatever
way would bring the desired result. This modern, positivist
attitude, where thought and analysis serve in so far as they
produce decisive action, rather than abstract concepts, lies
at the heart of The Prince.
Meanwhile Florence continued to drift. Machiavelli was
once again on the scene in 1503, this time in Rome, when
Borgia’s empire collapsed after both he and his father fell
seriously ill; legend has it that Alexander had accidentally
poisoned them both. The pope died and the son lost his