“I really don’t know him, so I’d prefer not to,” Pitino said when asked about Razorback’s HC. That quote alone sums it up. There’s respect there, but let’s not kid ourselves: the icy tension between Rick Pitino and John Calipari has outweighed the friendliness in their relationship. However, with the release of the NCAA Tournament bracket, there is a distinct possibility that the two coaching titans will match up against one another. And if it happens, it will be must-see TV.

Pitino and Calipari have been doing this for a long time. It started when both coached in Conference USA. It was only amplified with Calipari taking over at Kentucky, making him Pitino’s biggest roadblock at Louisville. Calipari has had the better of the matchups, leading their all-time head-to-head 21-16.

Now adding to their rivalry this season, the NCAA Tournament has put them in the same region, setting up a potential second-round meeting. But first, Rick Pitino’s No. 2 seed, St. John’s, must beat Omaha, and Calipari’s No. 10 Arkansas has to upset No. 7 Kansas. If both happen, we’ll get a March Madness grudge match for the ages.

The basketball world is already rife with speculation about what it could mean. As John Fanta put it on Field of 68 After Dark: “If Arkansas were to pull it off over Kansas, Cal and Rick despise each other; they don’t like each other. There is zero love lost. It would be an all-time press conference. Everything—the theater of that would be elite.”

While the match-up is on the cards, Pitino has not said much about going against Calipari, limiting his comments to talking about leading St. John’s to a deep tournament. After winning the Big East Tournament, he proclaimed, “I saved the best for last.” While Calipari commented on his team’s resiliency, “I’ve done this a long time, and this may be the most rewarding season for me because they are a bunch of good kids that struggled early.”

Even if we do get the Pitino-Calipari showdown, though, the path forward from there is brutal.

Rick Pitino vs John Calipari: Group of Death Showdown

The West Region features several heavyweights. No. 1 Florida, in search of a 3rd national championship, looks like a wagon boasting a scary two-way attack. No. 3 Texas Tech is another serious contender, highlighted by one of the most explosive offenses in the sport. And St. John’s? Under Pitino, it’s become a defensive juggernaut. No. 8 UConn, with back-to-back titles under Dan Hurley, looms as a potential Elite Eight foe, adding another layer of vengeance: Pitino’s 14-point win over Hurley’s Huskies on February 23, 2025, sparked a feud when Hurley called St. John’s ‘overrated.’ A Final Four run could see Pitino settling multiple scores, with Calipari’s upset bid just the opening act.

No. 10 Arkansas, No. 11 Drake, No. 12 Colorado State, and No. 13 Grand Canyon each have the potential to upset teams seeded higher than them, so they’re not here just to play a game and exit stage left, either. Missouri vs. Drake is one first-round matchup that’s already shaping up to be a tussle; Kansas vs. Arkansas is another. People are calling this region the “Region of Death” for good reason.

Rob Dauster of Field of 68 After Dark summed up the madness best: “Storylines are ridiculous, and here’s the other thing I love about it, guys. When I was kind of getting ready for Selection Sunday in my head, there were like seven or eight teams where I was just like, ‘Look, I want to try to find a way, no matter what happens, to get these teams into the Final Four.’ It was the four one seeds that we ended up with, right? It was St. John’s and Texas Tech. Those were three of the teams that I was like, ‘Hey, you know what? I think they’re going to try to get these teams into the tournament or to the Final Four,’ all kind of ending up in the same region. So I think that it is absolutely loaded in the West.”

If Pitino and Calipari win their first-round matchups, it will set up a second-round matchup with history, drama, and bad blood. The two have circled each other for years, and this time the tournament could force them into another clash at the highest stakes, all eyes on the sport trained on them.

March Madness always delivers, but this? This could be a tournament for the ages.