“The team had won a total of just two NCAA tournament games in the previous four seasons, and over the last two, it had lost twenty-seven games. That’s not supposed to happen in Lexington. There was nowhere to go but up.”
That is a direct quote from John Calipari’s book, Player’s First, which he published in April 2014, talking about the state of the Kentucky basketball program that he inherited in 2009, following Tubby Smith and Billy Gillespie. Nearly a decade later, those numbers are eerily similar.
Over the last four seasons, Kentucky has just one NCAA Tournament win, including two first-round losses to double-digit seeds. Over the last two, the Wildcats have lost 22 games. As Calipari said, that’s not supposed to happen at Kentucky.
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Through that span, people have blamed the lack of success on things like play style, recruiting strategies, and/or being slow to NIL amongst other things. But this was supposed to be the team.
A team “built for March,” Calipari said. A team that featured two of the best upperclassmen in the country. The no. 1 freshman class, which included three top 10 prospects and multiple projected NBA Draft picks. The stereotypical Calipari team, that featured elite freshmen and athleticism, playing in a revamped offense
While it created one of the most likable and exciting teams in recent Kentucky basketball history, it wasn’t enough for a single postseason win. The rosters have changed, the assistants have changed, but there has been one constant, John Calipari.
This is coming from a fan-turned-media member, soon to be 26 years old, who wrote voluntary school reports on Kentucky basketball. Whose first Kentucky basketball memories were towards the end of Tubby Smith’s career. Who cried at how bad Kentucky was during Billy Gillespie’s two seasons. Whose favorite birthday present on April, 1st 2009 was John Calipari being hired, as I learned on a school computer on ESPN. Whose Cal has treated nicely in every interaction and setting.
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Now, I have watched a team with multiple NBA players finish with the worst record in modern Kentucky basketball history. A team with the National Player of the Year, get beat by a 15-seed. Now a team with two top 10 picks and All-American lose to a 14 seed, almost single-handedly to a player that was playing Division III just two seasons ago.
“When we get it right, you notice we’re No. 1 in the country. We’re No. 1 seeds and we’re playing in Final Fours,” Calipari said in his Kentucky introductory press conference. Things don’t just feel “right” anymore.
Kentucky hasn’t been a 1-seed nor participated in a Final Four since 2015, nor been in reach of one since 2019. With each move Calipari makes, the Big Blue Nation becomes more and more divided.
John Calipari is a great man. He has done a lot, not just for Kentucky basketball, bringing four Final Fours and a national title, but also for this state and its people, raising millions and helping thousands of families. That said, Kentucky basketball is not meeting expectations, even by his own standards.
“I cannot tell you how hard the decision was because of what I left behind,” Calipari said of his decision to leave Memphis for Kentucky in 2009.
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Kentucky basketball is bigger than any coach. Walking off the court in Pittsburgh, following Calipari and the team to the locker room after the loss to Oakland, flooded with memories of the last 15 seasons, it feels like it’s time to make a hard decision.
Milan Momcilovic has officially announced that he will be playing his senior year of college basketball at Kentucky, suiting up in the blue and white for Mark Pope and the Wildcats!
BREAKING: Milan Momcilovic announces he is transferring to Kentucky!
Averaged 16.9 PPG last season and became the first in CBB history to lead the nation in 3P% (48.6%) & 3P made (136) in a single season.
The 6-foot-8 wing averaged 16.9 points per game in the 2025-26 season, leading the nation in 3-pointers made (136) and percentage from deep (48.7%).
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Momcilovic is mostly ranked as No. 2 in most portal rankings, but ESPN has the former Cyclone as the No. 1 overall player. With that being said, this technically serves as Pope’s first No. 1 transfer during his tenure at Kentucky.
Pulling his name out of the 2026 NBA Draft on Wednesday, May 27, Kentucky was seemingly the favorite to land the wing during the entire sweepstakes due to positional need, scheme fit and money available to spend. He could even play another year with the Kentucky Wildcats if the “5-in-5” rule is passed and he forgoes the draft again.
Putting Pat Kelsey in a locker and outbidding him on a recruit is always great for morale, but this fills the much-needed star spot for next year’s roster. Pope and his staff have shaped the team with plenty of skilled players, but Momcilovic adds that extra layer of shooting and will serve as the go-to guy when a game may be on the line.
This will be the final player added to the 2026-27 team, with an insert at the starting small forward position in Momcilovic’s future. Pope and the Big Blue Nation have their guy, and soon enough, we’ll see the Pewaukee, Wisconsin native on Rupp Arena’s court.
The Milan Momcilovic sweepstakes is underway, with multiple teams involved in the No. 2 overall transfer player’s recruitment. It is believed that Kentucky and Louisville are the top candidates after his decision to pull out from the 2026 NBA Draft on Wednesday, May 27.
Along with the in-state rivals, Arizona and St. John’s are both very well still in the mix, but the Red Storm are slowly falling out of contention after landing Baylor’s Tounde Yessoufou.
What an absolute BOMB from Shams.
For the wondering Kentucky fans, this basically has the Milan Momcilovic sweepstakes now between in-state rivals Kentucky and Louisville.
I fully expect the Wildcats to have the edge in this recruitment. Would be very surprised if the… https://t.co/xyWATR3UwE— Kai McClelland (@fourwal1) May 28, 2026
On May 28, national reporter Matt Norlander cleared the air on CBS Sports’ Eye On College Basketball podcast, stating that he believes Kentucky will land Momcilovic by the end of the weekend or Monday.
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“My prediction right now is that Milan Momcilovic will go to Kentucky,” Norlander said. “My understanding is that decision is going to come in the next one, two, three days, four days max.”
He would go on to talk about the other top programs involved, stating why he thinks they will be working in an uphill battle in this bidding war.
“My forecast is that it’s Kentucky, but you know, we’ll see if Louisville can get in there,” he continued. “Arizona I don’t think has the money to contend, like I think Kentucky and Louisville just have more money to play with.”
For the worried members of the Big Blue Nation, this is certainly good news to be put out by one of the most trusted college basketball reporters at the national level.
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Going by this report and Adam Zagoria’s from NYT Sports, it shouldn’t be long until a commitment decision for Momcilovic is announced publicly.
Per @AdamZagoria, Milan Momcilovic will announce where he will play his senior year of college basketball by the end of this weekend.— Kai McClelland (@fourwal1) May 28, 2026
Milan Momcilovic has officially removed his named from the 2026 NBA Draft and will return to college for his senior season.
Kentucky leads in his recruitment, followed closely by St. John’s, Louisville and Arizona. A backdoor to Iowa State is also still open.
The No. 2 ranked transfer would be a huge addition to Kentucky’s 2026-27 roster if he committed, averaging 16.9 points per game on 50.6/48.7/87.8 shooting splits last year. Funny enough, in the current world of college athletics that we live in, Momcilovic was responsible for eliminating the Wildcats from the NCAA Tournament, dropping 20 points in the Round of 32.
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He would go on to lose to Tennessee in the Sweet 16 with Iowa State, so at least we know that there’s some inner-hatred for a long-standing rival if he ends up a Wildcat.
He made the most three-point shots in Division I basketball and is a versatile 6-foot-8 wing, which would fit perfectly into Mark Pope’s offensive system. He completed workouts with the Chicago Bulls and Minnesota Timberwolves during the draft process.
Now, the bidding war for the top dog begins, with some of the most prestigious programs in the sport placing their bets on the star forward.