Ranking Kentucky's most painful NCAA Tournament losses in the Calipari era

My mother always said when you start dating someone there are only two possible outcomes: Either you get married or you break up. While I always thought that was just a sinister way to convince me to ditch a girlfriend she didn’t like, it puts breakups in perspective. A similar philosophy also applies to each Kentucky basketball season: Either the ‘Cats win the National Championship, or the season ends in agony. There is no in-between.

This type of pragmatic approach should help the coping process, but each year Kentucky doesn’t win a title, which is most of them, I find myself anguishing like a relationship with someone I loved ended horrifically.

In the wake of this melancholy, let’s hurl ourselves into the history of tournament torment, sprinkle in a dose of reflection, and figure out where this year’s loss to Oakland ranks in the most devastating NCAA Tournament exits in the John Calipari era.

Will it help? Probably not. Will it provide a little bit of clarity to a murky situation? Also, no. But what else do we have to do on a day when Kentucky should still be playing basketball?

The Wildcats have lost in the NCAA Tournament 11 times during Cal’s 15-year tenure at Kentucky. They won the National Championship once, which was awesome, and they missed the big dance altogether (or it was canceled) thrice. Less awesome.

Like you, I can recall with remarkable accuracy exactly where I was during every one of Kentucky’s tournament losses. That kind of trauma sticks with you, which makes grading that suffering like picking your favorite stubbed toe, or worse, permanent scar.

There are no easy losses on this list but for the sake of healing, here is my ranking of the Wildcats’ tourney exits from least to most painful.

11. Kansas State – Second Round (2023)

Coming off the most humiliating loss in Kentucky history in 2022, Kentucky limped into the 2023 Tournament without much to lose. It certainly couldn’t get any worse, especially as a 6-seed and expectations in the pits. Like every March, we feebly cobbled up hopes with phrases like, “Well if Cason Wallace can get hot…” but with turmoil surrounding Sahvir Wheeler and rumors of team discontent rampant, it was not a huge surprise when Kentucky fell to a guard shooting lights out. It hurt (badly), especially since it was in the second round, but with expectations so low, it ranks as the least painful on the list.

10. Indiana – Second Round (2016)

Kentucky won the SEC Tournament in dramatic fashion in 2016. It was my first-ever Nashville experience and it was incredible. Unfortunately, the selection committee did not think it mattered, as they gave runner-up, Texas A&M, the 3-seed and Kentucky the 4-seed. Unfortunately, Tyler Ulis and Jamal Murray could not keep their magical two-man show going, but their thrilling run through the SEC Tourney is something no one can take away, and in hindsight, eased the blow of losing to 5-seed Indiana, of all schools, in the second round.

9. Kansas State – Sweet 16 (2018)

In 2018, Kentucky was a 5-seed, and BBN’s expectations were somewhat down, relatively speaking, for a team that underachieved for most of the season. That being said, the bracket opened up like Moses parting the Red Sea and a Final Four berth was there for the taking. UMBC beat the 1-seed, Virginia, while in the bottom half of the region, Loyola-Chicago upset everyone they faced. That meant that all Kentucky had to do was beat 9-seed Kansas State and 11-seed Loyola-Chicago to earn a spot in the Final Four. Of course, that didn’t happen. The Wildcats failed to close out a winnable game against Kansas State and we had to hear about Sister Jean for the next two weeks.

8. UConn – Championship Game (2014)

Kentucky’s run through the 2014 Tournament was legendary. They beat Witchita State in what some consider to be one of the best second-round games of all time. They upended Louisville in a thriller only to turn around and do the same against Michigan in the Elite Eight. Oh, and then they did it on the biggest stage against Wisconsin in the Final Four. God bless Aaron Harrison. However, their sensational run came to an end against the slightly hotter Connecticut Huskies. The Wildcats never led in the game, and while it was tough to be so close to another banner but coming up short, the fun of that tournament run made up for it. Almost.

7. UConn – Final Four (2011)

Freaking, UConn, man. Kentucky has had more than its fair share of battles with the Johnny-come-lately blue blood and has been on the losing side of their matchups in March far too often. Kentucky’s first run-in with Kemba Walker’s crew came in 2011 in Houston. Having just missed the Final Four in 2010, Kentucky fans were ecstatic to get over the hump for the first time since 1998. The game was close, but the ‘Cats came up one point short to the eventual National Champions. Still, the joy of hanging a Final Four banner helped ease the sting. A little.

6. Auburn – Elite Eight (2019)

Kentucky has a knack for painful Elite Eight losses. There are two later on this list. There was the loss to Michigan State in 2005 after Patrick Sparks hit that dramatic 3-pointer to send the game to overtime. Oh, and I think something dramatic may have happened in 1992 against Duke, but it has been a while since I’ve seen a highlight from that game. Anyway, Kentucky lost in overtime to Auburn in the Elite Eight in 2019 and while not as high-profile as others, it cut deep at the time. It was the Wildcats’ third time playing Auburn that season, having won the previous two games. They were better than the Tigers AND one of Auburn’s star players got injured during the game…and Kentucky still fell short. Devastating.

5. North Carolina – Elite Eight (2017)

Kentucky and North Carolina were the two best teams in college basketball in the 2016-17 season, but it just so happened they got paired up in the same region. What many call the last exciting Kentucky team before this season, Bam, Fox, and Monk put on a show all year long, including defeating the Tar Heels in Las Vegas in what was one of the more entertaining college hoops games ever. But in the one that counted more, Luke Maye hit a game-winner as time expired to thwart another Final Four appearance for the ‘Cats. I’m still convinced had Kentucky won that game, they would have gone on to win the National Title. Ugh.

4. Oakland – First Round (2024)

Some of you will argue recency bias while others who are still numb will argue this should be ranked lower, but I’m putting Thursday’s loss to Oakland as the 4th most painful NCAA Tournament exit in the Cal era. This team was the most fun team in seemingly forever. With a legacy player in Reed Sheppard, a veteran scoring savant in Antonio Reeves, and a dynamic player-maker in Rob Dillingham, this team had all the pieces Kentucky fans love. To see it implode in the way of the second-worse tournament loss in program history…well it simply broke many Kentucky fans, and now has a not-so-small group calling for Calipari’s job.

3. St. Peter’s – First Round (2022)

This is the worst loss in Kentucky history. It is the third most painful on this list, but without a doubt, it is objectively the worst loss in the storied legacy of Wildcat basketball. To lose to a 15-seed as a 2-seed in the first round is not something that happens. Not at Kentucky. This team had ups and downs in the season, but they beat the eventual National Champions, Kansas, on their home floor and Oscar Tshiebwe became absolutely beloved. If it weren’t for some late-season injuries and general weirdness, who knows what could happened, but it will be a long, long time before Kentucky fans live this one down. It is still hard to process.

2. West Virginia – Elite Eight (2010)

It is not too often every fan remembers a specific defense that burned Kentucky, but this game is the exception. Stupid West Virginia and the 1-3-1 zone. What makes this loss more painful than the St. Peter’s one is just how incredible this season was. Cal’s first year was headlined by studs John Wall and DeMarcus Cousins and marked the return of Kentucky basketball. Kentucky was cool again. A stark turnaround from the Billy Gillespie days, this team became a global phenomenon. To see it melt away to a gimmick defense and an off-shooting night just one game away from a Final Four (to which I already had tickets and still attended for some reason only to watch Duke win it all)…well…it still hurts.

1. Wisconsin – Final Four (2015)

As I said earlier, I can recall with uncanny precision my exact location during every Kentucky tournament loss. However, walking out of Lucas Oil Stadium in Indianapolis in 2015, I can describe the sound of my slightly tattered shoes dragging the freshly laid pavement as I tried to find my friend’s car, halfway hoping it would never show up and I would wander aimlessly through the streets Indy for eternity. Just two games shy of a perfect 40-0 season, the pinnacle of accomplishment in the sport, nothing will ever crush my soul more than that Wisconsin loss. Especially since Kentucky had the lead in the closing minutes…especially since the refs missed a shot-clock violation that might have tipped the game…especially since Karl-Anthony Towns and Devin Booker were two of my favorite players. That loss will be the origin of my nightmares until the day I die.

Conclusion: The NCAA Tournament brings out all the feels

We all cope with grief differently. Some want to shut out the pain entirely. Others prefer to dive headfirst into it, wallowing in the pit of pinecones and darkness, absorbing all the hurt they can at once in an attempt to alleviate it long-term.

If you’re still reading this post, there must be at least some of the latter in you.

This list is not perfect. I get it. Depending on your situation at the time, certain losses may have impacted you more than others and that’s okay. Pain is subjective. essentially, this exercise was my melodramatic rendition of the Johnny Cash classic, Hurt.

Ultimately, however, we will get better. We always do. We will find another fish in the sea, fall in love again, and book both a chapel and a relationship counselor for next March just in case.

One of the things that makes Big Blue Nation beautiful is the shared experience of the highest of highs and lowest of lows. When you fistbump a stranger wearing a Kentucky hat, you’re not just saying, “We share a common interest.” You’re telling them we have ridden the same emotional roller coaster together over the years. I’ve celebrated when you celebrated, and I’ve hurt when you’ve hurt. And above all else, we will keep on going.