Kentucky has a $33 million John Calipari dilemma after March Madness failure

As Kentucky tries to make sense of its shocking loss to Oakland in the NCAA Tournament, the program could be facing a question with monumental implications. 

Could it be time to part ways with legendary head coach John Calipari? 

There are plenty of layers to the debate, but the program’s recent tournament shortcomings have started to raise some concerns after such incredible success prior to it. 

Kentucky had gone 26-1 between 1988- 2019 in the round of 64.

However, since then they’ve gone 1-2 with losses to a No. 15 seed and No. 14 seed.

There has been a growing chorus of Wildcats fans who would like to see Calipari out as head coach, and Thursday’s 80-76 loss to Oakland likely will harden those opinions. 

Even Calipari seemed to feel the weight of the loss when he spoke with TNT’s Evan Washburn. 

“I told them after, this one is painful,” Calipari said. “And the reason is there are other times you lose a game and you know your team is what it is. But this team, I really felt, was built for this moment. Even though we were young, I knew that could catch us. But we had our chances. We threw the ball away, took a bad shot. There were things that happened, and then we give up a corner three the last play.

“But you’ve got to give Oakland credit. They made unbelievable shots at the buzzer. They deserved to win the game. I hate to say we didn’t, but we didn’t.”

But the idea of cutting ties with Calipari isn’t cut and dry, and he would be owed $33 million if they attempted to buy out the rest of his contract now, On3’s Pete Nakos reported.

That means Kentucky will have to think long and hard about whether ending the relationship would be worth it, especially when the buyout cost dips to $27 million after next season.

The question would also become who would be Calipari’s successor if they opted to move on.

As of now, there doesn’t appear to be a clear-cut answer to that, which likely would factor into the decision on Calipari’s future with the program. 

Three straight seasons of early tournament exits and a year where Kentucky didn’t make the Big Dance has made the fans in Lexington anxious and now more than ever, and now Calipari’s future is a question mark.