Ranking the Top 50 Moments of the John Calipari Era: Nos. 50-41

Try and think of the most impactful moments of the John Calipari Era. This tenure has been WILD. In my initial try, I came up with 93 moments for consideration. And again, these are simply moments; they aren’t big-picture things like the recruiting classes of 2009, 2011, and 2013. They aren’t things like the one-and-done strategy or the dribble-drive offense. I decided to actually pick moments in time that define the John Calipari era. Things you can put a date on. And the word I considered most when making this list was IMPACT. Moments that truly had an impact, whether historic or short-term, on the Kentucky Basketball program.

Make no mistake, I didn’t only choose the good times. In many ways, the struggles have defined the Calipari era as much as the successes. The controversies are part of his tenure at Kentucky. Enjoy this trip down memory lane and appreciate the relevancy that has Cal brought back to Kentucky for the last 14 years.

Here are moments Nos. 50 through No. 41 today. Come back for the rest of the week for 10 moments every day:

No. 50: UK becomes first college basketball program to 2,000 wins (December 21, 2009)

The game itself was one of the more forgettable in the Cal era, an 88-44 win over Bruiser Flint and Drexel. UK led by 36 at halftime. But the significance of reaching the 2,000-win plateau was a great moment for Kentucky and John Calipari at the time and the fact it occurred right as Kentucky was ascending back to college basketball’s elite was symbolic. The Cats have since fallen behind Kansas in the all-time wins race but this moment really was something the fanbase needed after a rough four-year stretch.

No. 49: John Wall hits game-winner in UK debut (November 16, 2009)

Maybe some people forget but John Wall was suspended from the first game of the John Calipari era, a 16-point win over Morehead State. He made his debut in Game No. 2 against Miami (OH). And despite the fact that fans had to be a bit dismayed that Kentucky struggled to get past the Redhawks, they were treated to the first of many great Wall highlights, a mid-range jumper with 0.6 seconds remaining to secure the win. The excitement was officially back for UK basketball and John Wall was the star. It was Kentucky’s first game-winning shot with under two seconds to play since 2006.

No. 48: Malik Monk caught laughing on bench at the end of blowout loss to Florida (February 4, 2017)

I think many fans likely have forgotten what an issue this caused in the middle of the 2016-17 season. The issue was Kentucky was wrapping up their third loss in four games, this one a 22-point blowout at the hands of a barely ranked Florida squad. Monk went 4-14 in that game and then was caught by TV cameras laughing on the bench as the time wound down. Fans were already frustrated at that team’s play at that moment but felt insulted to see a player laughing following a big loss. It led to a good week’s worth of radio for sure. Of course, Monk and his teammates’ 14 consecutive wins following that game before losing in the Elite 8. But for “fan controversies,” this one does rank up there pretty high.

No. 47: Kentucky suffers worst SEC loss in Calipari era, drops stunner to South Carolina (January 10, 2023)

Look, Kentucky has lost a bunch of games to a bunch of teams over the years. Despite that, Kentucky has remained at the top or near the top of the SEC standings consistently under John Calipari and his teams have always feasted on the bottom of the league. That was especially true at Rupp Arena. So how bad was South Carolina? They lost to Tennessee three days before by 43 points. In their other four games against ranked opponents, they went 0-4 and lost by an average of 25 points. Their 4-14 SEC mark was the worst to beat a Kentucky team under Calipari. And they did it all largely by controlling a game on our home floor. It was, without question, the low moment of the season for John Calipari and Kentucky. And another reminder that Calipari had lost some grip on the program and the support of the fans.

No. 46: UK beats undefeated Wichita State in 2nd Round of NCAA Tournament (March 23, 2014)

When it comes to the quality of a game played under Calipari, this might be the best game we’ve seen. But its significance only became greater once the Cats did what they did in the three games that followed it. Even still, beating a No. 1 seed who was 35-0 coming into the game was significant. The regular season had been a tremendous disappointment and despite some signs of improvement in the SEC Tournament, there still were very few signs that UK could compete with Wichita State. But this game was where this team finally realized its potential. Also James Young “forgetting the play” to win the game will always be funny. I will add that coming off an NIT 2013 team and the potential for this season to be a bust with a loss, Calipari really saved himself some upset fans with this win.

No. 45: PJ Washington misses 12 free throws in stunning Sweet 16 loss to Kansas State (March 22, 2018)

There has never been a path to the Final Four gifted to Kentucky more than in 2018. Their path would have been against a 12, 13, 9, and 11 seed. After impressively handling their business in Boise against Davidson and Buffalo, many Cats fans headed to Atlanta believing the Final Four was all but certain. But, in what has become a string of very disappointing tournament losses, the Cats came out flat against a spunky K-State squad, fell behind early, and then were doomed by 12 missed free throws by PJ Washington. I had honestly forgotten there were that many misses. But while those free throws were crucial, that team’s complete inability to shoot the ball led some to question if the style of play in basketball was starting to pass Calipari by. And that question remains today.

No. 44: John Robic No Longer a UK Assistant (December 20, 2021)

I simply chose the date his wife posted he was no longer with the program in any capacity. Nonetheless, Robic’s time as a head assistant under Calipari from 2010-2016 is truly one of the most remarkable runs in school history. And since his departure from the bench, there have been many questions arise about gameplan and strategy, as well as Calipari’s overall relationship with assistants. So I do think Robic’s transition, no matter what the date or true details behind it, was a very impactful moment for the program. (Sidenote: You could probably make a case for Kenny Payne’s departure to the Knicks as well, but I think Robic was more impactful.)

No. 43: Aaron Harrison says “It’s Gonna Be a Great Story” following stunning South Carolina loss, Cal ejection (March 1, 2014)

It probably wasn’t a moment John Calipari was too proud of. But it took a lot of guts for Aaron Harrison to exude that kind of confidence following what appeared to be a season-shattering loss to one of the worst teams in the league. Not the mention, it appeared Calipari had lost control too after getting ejected during the game. But Harrison seemed to know the team had the potential to turn things around and he backed it up with three of the greatest shots in school history over the next month.

No. 42: Oscar Tshiebwe named National Player of the Year (April 5, 2022)

With his announcement as Wooden Award winner, Oscar became the second consensus National Player of the Year, joining Anthony Davis. But while Davis was thought of as an All-American talent, Oscar’s season largely came out of nowhere and statistically, was unmatched in the Cal era. His rebounding stats are almost still hard to fathom and the consistency with which he performed that season was remarkable. With a better tournament run, Oscar would have likely had an argument to be the 2nd or 3rd best player of the Cal era (and he still might anyway).

No. 41: Zion Williamson chooses Duke over Kentucky (January 20, 2018)

If you believe the UK program is not where it used to be under John Calipari, many will point to this date. As you will see in another moment later this week, I think seeing Zion on the court was a bigger moment, but this was significant as well. It wasn’t just that Zion didn’t pick Kentucky, it’s that he picked Duke. And he picked Duke somewhat surprisingly. I didn’t realize this until I watched the video below, but during his announcement, he didn’t even mention Kentucky. He mentions Duke, Clemson, and South Carolina. When it comes to an unexpected whiff on the recruiting trail, of which there have not been many, this has to be at the top in the last 13 years.