I don’t really know how many more titles he might have won. Say that he won a couple more championships, does he get complacent and just start skating by doing enough to please the masses but not really a threat to win it all? With his failure with the Celtics, that was his motivation to prove he is still a HOF Coach that wants to win more than anyone. I would say maybe 3 more, max 4 championships if he stayed, UK ages men a lot quicker than most women, married men, can attest, then add both and maybe a side hustle. Pitino would look worse than the Crypt Keeper.