Five major questions for this Kentucky basketball offseason. Starting with John Calipari.

There’s been no such thing as a boring Kentucky basketball offseason since John Calipari took over the Wildcats’ program 15 years ago.

Even by those standards, this one should be a doozy.

Stay-or-go decisions involving high-profile UK players. Possible changes to the coaching staff. The potential to add an impact player or two (or more) from the transfer portal or elsewhere. All of those things have been worth watching every spring and summer during the Calipari era, and they will be again this offseason.

This time around, the future of Calipari himself is at the top of the list.

With Kentucky’s season-ending loss to Oakland in the first round of the NCAA Tournament still fresh, here are five questions on what comes next for Kentucky basketball.

What’s next for John Calipari?

The first major decision of this offseason will be figuring out what’s next for John Calipari, who just wrapped up his 15th year as Kentucky’s head coach, a job he said in 2009 was one that no one should do for more than a decade. In part, that’s due to the pressures involved, and there’s never been more pressure on Calipari than there is now.

The Hall of Fame head coach turned 65 years old last month and still has five seasons remaining on a 10-year contract extension signed in 2019, but many Kentucky fans have already seen enough, even as this current deal has only now reached its halfway point.

Calipari spoke Thursday night like a man who fully expects to be back in Lexington at the beginning of the 2024-25 season. Even if he’s open to other jobs, that’s the public stance he would take. He said he had “no interest” in leaving Memphis mere days before doing just that in 2009, knowing the Kentucky job opening was the reason it was a talking point at the time. It’s what college coaches in this position do all the time.

That said, the most likely scenario is that Calipari will indeed be back for his 16th season unless UK’s wealthiest donors pay him to leave. He’s not going to walk away from the nearly $45 million he’s still owed. UK isn’t going to pay him the more than $33 million it would be required to pony up to send him on his way, unless they get that money from outside sources. There is still a chance that could happen. The Herald-Leader has been told that there have been preliminary talks exploring the possibility of a buyout involving UK Athletics mega-donors Joe and Kelly Craft, as well as others with deep pockets and a history of giving to the athletics department.

Jumping ship to another school remains a possibility, but the odds of that seem slim. There are only so many places in college basketball that would make for a proper fit — the NBA is surely out of the question at this point — and none of them offer the possibilities available at Kentucky. If Calipari ends up elsewhere next season, it probably won’t be his first choice.

Calipari has never been one to run from adversity. He took a UMass job nobody wanted and turned the Minutemen into a Final Four program. He then jumped to a New Jersey Nets franchise that had won one NBA playoff series in its first 19 years in the league. He got fired there, went on to rebuild Memphis and then brought Kentucky back to the pinnacle of the sport.

Leaving of his own volition for a lesser job is not the Calipari way.

So, unless a traditionally stubborn, highly successful 65-year-old man decides at the end of his career that he’s going to drastically change his way of thinking — or those wealthy donors pledge the more than $33 million to fund his buyout — Calipari will be back with the Cats next season.

If that does indeed happen, then what happens next?

Will Calipari make changes?

Based on conversations in the immediate aftermath of Kentucky’s loss to Oakland on Thursday night, no one close to the situation thought there was a more likely scenario than Calipari coming back for a 16th season in Lexington.

That could shift in the coming days — this is a fluid situation — but, if there is a 16th season of the Calipari era, what would it look like?

In recent years, Calipari has brushed off criticism of head-scratching losses in the regular season by reminding his detractors that everything he does is with March in mind. And when his Cats have stumbled in NCAA Tournament play, he acknowledges but also laments that good seasons go uncelebrated just because of one bad loss.

Obviously, he can’t have it both ways.

Calipari has got to figure out a way to win in March again. It’s now been six years since he advanced to an SEC Tournament title game. In the past four NCAA tournaments, the Wildcats have exactly one victory. That’s inexcusable.

For this season, Calipari went all-in on freshmen, the strategy that led to so much winning in his early years on the job. But college basketball has changed since then, and going this direction with this team — 10 of his 12 scholarship players were underclassmen, eight of them freshmen — was criticized even before a single game was played.

Those criticisms proved warranted.

“They’re freshmen! We don’t know how they’re going to respond in this stuff,” Calipari said of teenagers playing in an NCAA Tournament atmosphere after Thursday’s loss, where his two upperclassmen were his two best players.

And yet, a few minutes later …

“I don’t see myself just saying, OK, we’re not going to recruit freshmen.”

Calipari talked about the idea of recruiting more older guys, then noted that he’d already tried it, pointing out that fifth-year players Tre Mitchell and Antonio Reeves, both experienced transfers by the time they got to Kentucky, had just been sitting next to him on stage. He also had experienced players — and went nowhere in March — the two previous seasons.

Instead of answers to questions Thursday night, Calipari simply had more questions. “So do I change because of that?” he asked, referencing the college basketball landscape that’s shifted in recent years to older players. That question was not rhetorical. It sounded like an actual question. Calipari better figure out the answer.

He already has six new freshmen coming in, none of whom appear to be of the John Wall, Anthony Davis or Karl-Anthony Towns variety. What will happen to the remaining roster spots? The next Kentucky basketball season depends on Calipari finding the answer.

It also won’t be a surprise if there are changes within Kentucky’s coaching staff. Current NCAA rules permit five full assistants. Chuck Martin and John Welch came in on two-year deals before this season and have both been widely lauded as good hires.

Current contracts for Bruiser Flint and Orlando Antigua are up at the end of June. Both have extensive histories with Calipari, who first hired Flint at UMass 35 years ago and counts him among his closest coaching confidantes. Antigua, long renowned as a top-notch recruiter, was with Calipari at Memphis.

Chin Coleman still has one season remaining on his contact — following an extension two years ago — and is due to make $650,000 in 2024-25. He, too, has a reputation as a recruiter, but Coleman was also the assistant publicly stated to be in charge of UK’s defense, which sat 114th nationally in the KenPom defensive efficiency ratings Friday morning, the worst mark of Calipari’s tenure at Kentucky.

Calipari will have some difficult decisions to make in the coming weeks. If he is back for a 16th season, some of those decisions might be made for him.

Who returns to Kentucky?

Of course, who’s actually on the UK basketball roster come November will have a major impact on the 2024-25 season.

Calipari has his six freshmen. Who else might join them? Reeves and Mitchell are out of eligibility. Rob Dillingham is gone. Justin Edwards most likely is, too. Of Kentucky’s trio of 7-footers — Aaron Bradshaw, Zvonimir Ivisic and Ugonna Onyenso — it would be a major stretch to expect more than one to return, especially with big men Jayden Quaintance and Somto Cyril already committed for this year’s recruiting class. All three of those current UK bigs leaving might be the most likely scenario.

The three biggest names to watch in the coming weeks are Adou Thiero, D.J. Wagner, and, of course, Reed Sheppard.

If Calipari can get those three back, he’d go into next season with an enviable roster, no matter what else happens this summer. But none of those players are locks to return. All three were asked about what’s next by the Herald-Leader on Thursday night. Understandably, none offered any insight into their immediate futures. All will sit down with family and other advisers in the coming days to weigh their options.

Of the three, Thiero is the most likely to be back, and he could be one of the SEC’s breakout players next season. There’s real buzz that Wagner — still just 18 years old, with his current NBA draft stock limited and a deep family history with Calipari — might very well return.

Sheppard, the national freshman of the year, is obviously the one who will get the most attention. He dreamed his whole life of playing for Kentucky, and losing his only NCAA Tournament game as a Wildcat is not how he imagined that UK career would end.

In his heart, Sheppard would surely love another chance. But as time goes on, he and his family will be looking at the bigger picture, and turning down the guaranteed millions that would come with a one-and-done entry into this year’s NBA draft will be tough to do.

Unless there are some unexpected returnees, Calipari will surely be looking into the transfer portal. That window is already open, and more and more talented players will be adding their names in the coming days. Kentucky’s next roster likely won’t be settled for months.

What is the national perception?

Even as a vocal segment of Big Blue Nation raged — from social media to family get-togethers — in recent years, the overwhelming sentiment outside of the commonwealth was something else.

Up until Thursday night, if you told a smart college basketball person — a veteran coach or national pundit, for example — that a decent number of Kentucky basketball fans wanted to run Calipari out of town, you’d get a look as if you had two heads. This was an inconceivable thought to many in the business. The guy has four Final Fours at UK (six total), he’s in the Hall of Fame, and — actual results aside — his recent teams at least entered March Madness appearing to be a threat.

Some of these folks understood the consternation, even if they thought it was overblown. Others couldn’t even fathom such a thing.

It’ll be interesting to see what those reactions are moving forward.

Following the loss to Oakland, the cracks were already starting to form, with some smart college basketball observers calling for an end to the Kentucky-Calipari marriage. These were some of the same people who — even 24 hours earlier — wouldn’t have gone nearly that far.

Yes, Kentucky has been really good in two of the past three seasons, spending much of both ranked in the top 10 nationally. Those seasons ended with losses to a 15 seed and a 14 seed in the NCAA Tournament. In the season between, Kentucky returned the national player of the year — the first time that had happened anywhere in more than a decade — began the season ranked No. 4 in the AP poll and then needed a strong finish to SEC play just to make it into the NCAA Tournament field. Yikes.

Who cares what the “national people” think? Well, fair question. In this case, those national narratives drive perception. And the perception of Kentucky basketball is quickly crystallizing into a consensus. The era of Calipari and the Cats being the undisputed kings of cool in college basketball has faded. That has an effect on recruiting, among other things.

The only way to reverse this course? Winning. And lots of it. In March. And April.

Tall task, especially given the recent results.

How will UK fans respond?

Losing to Wisconsin in the Final Four nine years ago remains a feeling that some can’t shake.

Falling in Elite Eights in 2017 and 2019 — both games well within reach, with realistic paths to a national championship from there — compounded the angst.

Most Kentucky fans seemed OK giving Calipari a pass on the terrible 2020-21 season. It was a team of freshmen trying to come together during the social-distancing measures of the COVID-19 pandemic that limited practice time and doomed that roster from the start. (Although it’s fair to question if that group would’ve done much anyway, even under the best of circumstances.)

And then Saint Peter’s happened, and nothing from a fan perspective has really been the same since. Other than it’s actually worse now than it was in the days after that defeat two years ago. Oscar Tshiebwe came back, and Kentucky ended up being a 6 seed. Opportunity lost.

Then, this season’s talented bunch of likable freshmen arrived, Kentucky folk hero Reed Sheppard thrust into the role as face of the most-fun UK basketball team in years. Fans were hesitant to hand over their hope at first, hurt too deeply and too often in recent years. That one end zone in the upper level of Rupp Arena still had plenty of empty seats at the beginning of this season, even as Sheppard and Rob Dillingham and the rest were doing their thing on the court.

And then those empty seats started filling up with people. And Rupp got loud again. The Miami game. Big Z’s debut. Dropping 117 points on Nate Oats and Alabama.

This Kentucky team captured the imagination of Big Blue Nation like no other group of Wildcats had in years, maybe not since that first season of the Calipari era, when John Wall danced the Billy Gillispie-era blues away and all was right in Rupp again.

The goodwill of the past few months vanished as soon as that buzzer sounded Thursday night. All gone. Another opportunity lost. And much of the fan base along with it.

Even if Calipari is back, people will still show up in droves for Big Blue Madness seven months from now, and the seats will be mostly filled when the Wildcats tip off their first home game of the 2024-25 season. But it’s clear that a large contingent of Cat fans have reached the “won’t get fooled again” stage of the Calipari era. For real this time.

The only thing that might bring most of them back would be the return of Reed Sheppard, and that’s way too much to put on the shoulders of a 19-year-old who’s already carried so much of that weight with him these past several months.

The pressure now belongs on John Calipari. All of it. And until he brings another banner to Rupp Arena, there’s a sizable segment of this fan base that won’t care nearly as much about the games he wins between November and February.

It’s always been March that matters most around here. For many, it seems, that’s now the only thing that will matter for the remainder of the Calipari era, however long that might last.

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