Yes, it's another Borgia thread
Cesare Borgia didn't manage to take Bologna as he had the other city states - Forli, Imola, Faenza, Rimini, Pesaro etc. In retrospect this was a flaw in the plan, as instead of deposing the Bentivoglios as he had the Sforza, the Manfredi, the Malatesta etc, he signed a treaty of perpetual friendship with them on 30 April 1501.
Bologna and Perugia held out against the papacy until
il papa guerriero, Julius II, conquered them in 1506. Julius commissioned Michelangelo to make a large bronze statue of himself, that when the Bentivoglios retook the city, the Bolognese broke it down and sold the bronze to the duke of Ferrara. Said duke - former brother-in-law of Cesare, melted the bronze into a cannon named
La Giulia.
That said, what if Cesare Borgia manages to take Bologna in 1501 instead of only signing a treaty with them?