Pope Julius II
Formerly Giuliano della Rovere, cardinal of San Pietro ad Vincula.
Do you think the Vatican has a military version of the papal robes, for when popes wage war? You know, something without the funny hat? Pope Julius II would have needed them. This is our quintessential warrior pope. Just like Borgia, he was following in Alexander's footsteps. Only this approach doesn't work out too well for Borgia, since Julius steals all of his lands. We guess fortune demands that there be only one successor, and it seems that successor isn't Borgia.
Speaking of luck, Machiavelli says that the main difference between Julius and Cesare is that Julius, unlike Borgia, was a very lucky guy. His "decision to put himself entirely in a foreign army's hands merely to take Ferrara could hardly have been more rash. But he was lucky and the unlikely outcome of the campaign spared him the possible consequences of his mistake" (13.2). Luck makes the difference between disaster and success.
This foolhardy action seems to be Julius's standard mode of operation, because later Machiavelli spends a whole bunch of paragraphs talking about how impulsive and rash he is. Really, he probably shouldn't have been as successful as he was—and if he'd stuck around longer, maybe he wouldn't have been. Machiavelli writes, "His early death spared him the experience of failure. Because if times had changed and circumstances demanded caution, he would have been finished" (25.9).
The point is that Julius just kept going, even if it was kind of stupid—and even if maybe he should have thought about it a little more. Luck, it seems, was on his side. Remember what Machiavelli said about virtù? That it gives you the key to drive Fortune's car? Julius has definitely been going on a joyride, never mind that—according to Machiavelli—he never got his driver's license.
Luck likes it when you take a chance, so better to be impulsive and rash like Julius than indecisive, like that dude whose name we don't know because he's not famous. Luck or virtù? It seems like one's no good without the other.