Oliver James Montgomery-Another March Madness disappointment means it's time for Kentucky and John Calipari to part

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At some point in the next few days, John Calipari and Kentucky officials need to get in a room, lock the door and agree not to come out until they’ve reached a number that will end this agony. 

It’s over. 

It needs to be over. 

It’s time for college basketball’s premier program and the sport's most underachieving coach to go their separate ways and do something different. 

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If Calipari returns to Kentucky next year after another March disasterclass — this time a loss to Oakland Thursday in the first round of the NCAA men’s basketball tournament — he will be the most miserable multi-millionaire in a state that no longer wants him there and no longer envisions a revival in whatever magical abilities he once had. 

So what’s the point? 

It was a good run for Calipari at Kentucky. Not a great run, but a good one: 15 years, four Final Fours, one national title. Not bad. Also, not what was expected or what it should have been given the turnstile of five-star prospects he brought in and sent on to NBA stardom. 

But even letting national championships slip away, which was Calipari’s modus operandi a decade ago, feels like a long journey from the current reality at Kentucky. At this point, just getting out of the first round seems like a chore. 

Kentucky couldn’t do it in 2022 against No. 15 seed Saint Peter’s.

And they couldn’t do it Thursday against the No. 14 seed Oakland Grizzlies and a 24-year old grad student named Jack Gohlke, who spent most of his college basketball career at Hillsdale College. 

Calipari gets the John Walls and Devin Bookers, the Karl-Anthony Townses and Anthony Davises. Oakland coach Greg Kampe gets transfers out of Division II who torch the lottery picks for 10 three-pointers. 

It’s so NCAA tournament. 

It’s also so Calipari. 

“Our team shouldn’t be defined by that game, but it will be,” Calipari said in a post-game interview on CBS. “This is the profession we’ve chosen, but you know, we had some guys that didn’t play the way they’ve been playing all year.”

It’s true. Kentucky played an awful game, in particular Reed Sheppard who has been lights out all year but looked like a freshman on the big stage.

But who failed to get his team in a loose, confident frame of mind and ready to dominate a team of significantly lesser talent? Who was too slow to make adjustments on Gohlke while his shooting set the tone and gave Oakland confidence? Who watched helplessly while his team crumbled in the final four minutes and made mistake after mistake? 

It’s Calipari. It's always Calipari. 

And Kentucky fans who take great pride in this program know deep in their gut that this marriage has run its course. They haven’t been a real factor in the national championship conversation since COVID-19 — haven’t come close to that level. In fact, Kentucky’s postseason record (including the SEC tournament) since 2019 is a disastrous 2-6. 

At Kentucky, four years of mediocre basketball is a long time. At Kentucky, it usually gets you fired. 

So what happens now? 

If Kentucky wanted to fire him, it would owe almost $35 million. That’s a massive sum of money the school will likely be hesitant to pay even if it knows how toxic the environment will be if he comes back. 

And as much as Calipari likes money — maybe more than anyone in the history of college athletics — it’s hard to see him walking away without getting what he believes he deserves.

The best course of action would be to get together, admit that this isn't working anymore, and come up with a settlement that satisfies Calipari’s ego and allows him to say he’s done all he can do at Kentucky and it’s time to move on. 

Over the course of his career, Calipari has dealt with plenty of negativity. But what awaits him next season at Kentucky would be an entirely different level, to the point where it would impact anyone’s quality of life. 

It’s not worth it. 

Calipari is 65 years old now, and if he chooses he can walk away from college basketball as a Hall of Famer, a national champion and wealthy beyond his wildest imagination. If he wants one more coaching shot somewhere — and there are several good jobs that are either open or will be open in the coming days — he needs to make that move now. 

Whichever path he chooses, it doesn’t matter. 

As long as he’s not back at Kentucky — for his own sake as much as the school’s.