Both resurrected what seemed to be a dead Kentucky team. Both are Italians from the east coast, with Pitino from New York and Calipari from Pennsylvania. Both have won championships at Kentucky and reached Final Fours with two other schools.
Both are known currently as two of the best coaches in the game as well as two of the best recruiters. They are also the two best coaches in Kentucky's history (sorry, Adolph Rupp).
However, with the Wildcats and Cardinals squaring off this week, there's one question that needs to be answered: Which of these rivals is the greater coach at Kentucky?
The answer: John Calipari.
Sure, Pitino took over a team that was left for the ashes when Eddie Sutton caused Kentucky to face probation for a recruiting violation. Sure, he took Kentucky to the promised land with a national championship in 1996.
Sure, he coached in the greatest game ever played, losing to Duke in the Elite Eight in 1992. Sure, he should have won three consecutive national championships, and was only spoiled by Arizona in 1997 before leaving for the NBA while Tubby Smith won in 1998 with Pitino's players.
But the difference is that Calipari has brought Kentucky to a different level. Kentucky has been called the Roman Empire of college basketball. But unlike the fall of the Roman Empire, there is no fall for Calipari and Kentucky.
They are at the peak of college basketball, and it's all thanks to Calipari. He took a team that was coming off an NIT berth, low-ranked recruiting classes from then-head coach Billy Gillispie and losses at home to teams like Gardner Webb, San Diego, Georgia and VMI.
That's unheard of with Calipari. His down year has consisted of a 10-6 SEC record, but a berth in the Final Four. He has racked up 110 wins through his first three-plus seasons in Lexington, and there seems to be no decline in his passion.
Recruits are flocking to Big Blue Nation at an unbelievable rate. He has had three classes ranked first overall, and the class coming in next year has the chance to be not only his best recruiting class ever, but the best in college basketball history.
Calipari is doing all of this with even more pressure than Pitino had. Coming off of probation, Pitino was expected to slowly bringing Kentucky back to its rightful place at the top of the college basketball mountain. But the moment Calipari walked into the Joe Craft Center for his welcoming press conference, he was expected to bring Big Blue Nation national championships.
Calipari also has a lot more obstacles in his way when it comes to recruiting than Pitino did after the probation ended at Kentucky. Calipari has to deal with shoe deals with colleges and AAU teams, the chance to play in Europe and the run for the NBA money.
Also, the NBA. In the 1990s, it was unusual for players to leave college early for the pros, where it's vice versa in today's world. Calipari has to deal with talented players, mostly for one year, and convince them to come together and compete for a national championship.
That makes Calipari not only one of the most underrated in-game coaches in the game today, but also the greatest basketball coach in Kentucky's history.
Pitino may have built Kentucky into the Roman Empire, but Calipari has made Kentucky immortal.