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Cesare Borgia isn't on death's door when his father Alexander IV dies. He is alive and well, manages the Papal elections, and continues his expansion. Machiavelli believes that Cesare is the Italians best hope of unification, and when Cesare makes it clear that he is going after the city, Machiavelli brings the city peacefully into Cesare's expanding polity, and become Cesare's chief political adviser, acting as his "Prime Minister" if you will. Machiavelli's radical ideas about the use of citizen-soldiers is seen as one of the building blocks of Borgia's Italian state . . .
 
That assumes however that Machiavelli would have totally abandoned Florence whatever, and that Borgia would have liked Machiavelli more than just treating him as a mere Florentine official

Abandoned Florance? On the contrary, he is acting as a true Italian Patriot . . .
 
Remember Machiavelli himself considered Italy as just a geographical expression. He dismissed an Italian Union as nonsense, given that Italian states could never stand united.

He thought the Union was non-sense, but if you read the Prince, it is clear that he didn't believe that dis-united peoples couldn't be united. His use of the Athenian and Persian founding heroes as examples of leaders who united their respective nations makes it clear that he considered it necessary for a single strong leader to be the driver behind unification.

If Cesare survived Alexander IV's death, then I think that Cesare Borgia would have increasingly appeared to be the man destined to unite the Italian people, and that would most definitely draw Machiavelli's attention. Borgia wasn't interested in bringing the Italian states together on equal terms, he was trying to conquer them. He didn't want a Union, he wanted a Kingdom.
 
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