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There’s never been more pressure on John Calipari to make an NCAA Tournament run. Kentucky just flamed out in a fifth consecutive SEC tournament, where the Wildcats have won two total games since 2018, and Calipari has but one lonely victory in the big dance since 2019.

The last time UK failed to make at least the Sweet 16 in four straight tournaments — as Calipari is now in danger of doing — was 2006-09, the final two years of Tubby Smith and the only two years of Billy Gillispie. What’s weirdest about Calipari’s recent struggle in March is how consistently good he used to be this time of year.

From the end of his time at Memphis through the first six years at Kentucky, Calipari made the Sweet 16 in nine consecutive tournaments, reached the Elite Eight in eight of those, got to the Final Four in five of them and played for the championship three times. The last Final Four was 2015, though, and that all seems like a long time ago now.

Calipari needs a run in the worst way. So what would the path to one look like this year? The Wildcats, a No. 3 seed in the South Region an opening play in Pittsburgh, will have Oakland first and the winner of a 6/11 game between Texas Tech and N.C. State, which just won five games in five days to earn the ACC’s automatic bid. No. 2 seed Marquette or SEC rival Florida would most likely be waiting in the Sweet 16.

Get to an Elite Eight, the program’s first since an OT loss to Auburn in 2019, and a couple of must-see matchup possibilities exist. No. 1 seed Houston and perhaps the toughest defense in America against UK’s thrill-a-minute offense? Or could it be hated rival Duke for a trip to the Final Four? If Calipari wants to reclaim godlike status in the Bluegrass, beat the Blue Devils in a regional final.

Considering its roller-coaster season and nine losses, Kentucky can’t complain much about this draw. It’s pretty reasonable. Not the gauntlet Cats fans have come to expect. There are some big potential challenges, sure, but this is hardly an impossible path. And UK already owns regular-season wins over a No. 1 seed (North Carolina), No. 2 seed (Tennessee) and two No. 4 seeds (Auburn and Alabama). Calipari’s team is good enough and the bracket is manageable, so now the Hall of Fame coach needs to get it done.

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