What if, back in 1997, Pitino thanked the Celtics but turned them down and committed to being the head coach at Kentucky. I know people may say now that they hate Pitino, but if you could of had him stay and build his own dynasty at UK, where do you think we'd be at the moment? I can't imagine anyone would have NOT wanted him to remain as our coach back then, regardless of how they feel about him now.
First off, Dirk Nowitzki and Tracy McGrady may have been Wildcats. Jermaine O'Neal too. I think Michael Bradley sticks around for the full four seasons instead of transferring to Villanova. That being said, if Pitino had stuck around until now, making him the 2nd longest tenured coach at UK behind Rupp at 26 seasons, going on 27. With the pedigree of being the coach at UK and the atmosphere around the program, I think he avoids a lot of the pitfalls that have plagued him at UL.
During his 6 non-probation seasons at UK, he produced a round of 32 team, two Elite Eight teams, a Final Four Team, A National Runner-Up, and a National Championship team. I don't think it is reaching too far to assume that he would have kept that trend going, finishing the 90's with another National Championship (probably 98 or 99) and spending much of the 2000's as the premiere program in college basketball going to multiple Final Fours and winning (at least) another National Championship. I'd imagine he'd have begun to slow down a bit by 2010 without much pressure from the program down the road and by 2015 would have produced another couple of Final Fours and another National Championship, bringing his total titles to (at least) 4.
Pitino is a great coach, but I think he greatly diminished his legacy in basketball the day he left for Boston. Had he stayed here I firmly believe he would be considered among the all-time 4 or 5 greatest coaches to ever coach the game. As it is, he's still a hall of famer, but I dont think he'll ever be considered among the top 10 all-time.