On Tuesday, he'll be in a 3,000-seat gym in Moon Township, Pa., wondering if his team has enough gas left in the tank to win a game in the National Invitational Tournament.
It's been a year of stark contrast for the Kentucky program, and one that continues to baffle Calipari.
"One thing is, I have no regrets because I've tried everything," he said. "(It's) humbling because it's probably the first group in a long time that wouldn't respond and change… I learned a lot of lessons that our staff is taking into account as we go forward. What kind of team we have. What kind of personnel we have. What kind of mentalities we have – the guys that we've always had in the past.
"You know it's a great learning experience. Hate going through it. I'd rather learn from someone else's issues than my own. This was hard. I feel good, but it was hard going through it."
Kentucky finished the regular season at 21-10 and appeared to be in good shape for an at-large NCAA Tournament bid after finishing second to Florida in the SEC and knocking off the Gators on March 9. But the Wildcats "laid an egg," as Calipari said, in a 64-48 loss to Vanderbilt last week in the SEC Tournament quarterfinals and were passed over in favor of programs like LaSalle, Boise State and Middle Tennessee for the final bids in Sunday's NCAA bracket announcement.
That sends UK to the greater Pittsburgh area for a matchup with Robert Morris, but most fans in the Big Blue Nation are focused on next season more than salvaging some pride and padding the all-time wins lead in the NIT.
Five-star Texas forward Julius Randle is expected to choose between Kentucky and Kansas this week.
The current signee list is already an embarrassment of riches, featuring five-star Texas twins Andrew Harrison and Aaron Harrison, the nation's No. 1 point guard and No. 1 shooting guard, respectively. It also includes No. 1 center Dakari Johnson, No. 2 center Marcus Lee, No. 3 small forward James Young and three-star in-state prospect Derek Willis.
If any of the big three undecideds join the party, some analysts believe Kentucky would have the greatest signing class in history, but there could also be some roster management issues that have to be addressed. NCAA rules limit teams to 13 scholarship players; UK sits at the limit with players who are eligible to return, plus the fall signees.
"We will sit down and talk about all that stuff when the time is right," Calipari said, "but that's when the season is over."
The UK boss has hinted that there are players on his current roster than he hasn't been able to reach.
Will sophomore point guard Ryan Harrow be back after an emotional roller coaster of a season which last saw him weeping in the locker room at the SEC Tournament after going 2-for-15 from the field with four turnovers against Vanderbilt, a game which he said cost his team an NCAA tourney bid?
Will freshman combo guard Archie Goodwin test the NBA waters? The same question looms for freshman forward Alex Poythress and freshman center Willie Cauley-Stein in what many analysts say is a historically-week NBA Draft. All three are consistently listed as potential first-round picks.
Will there be a surprise transfer? Or will freshman center Nerlens Noel, coming off knee surgery, shock the world and return for another season at UK with a good opportunity to win a championship?
Only one thing is certain: Calipari won't change his approach to building a roster. So-called "one-and-dones" aren't the problem, he says. "Nope. Nope. Nope. I like that national title. I like that national title."
Asked if he'll change his approach with next year's team, Calipari said he'd likely be more patient, but he thought more competition would push the players harder than he could himself.
"We are bringing in other guys, so you have to step up," he said. "But this (current roster) may be a group of four-year players. There is nothing wrong with that. Why is everybody panicked? So they're four year players… So? You get another group, and now you have a nice, big team, and you take on the world."
Calipari said he has also learned that he needs to look beyond the physical skills of the players he recruits in the future and make sure they're prepared for the mental side of playing basketball at Kentucky.
"I will look for guys that can deal with us as coaches, me as head coach, and that can play with the mentality we want them to play with," he said. "We have to be more precise in that. There is a certain toughness that you have to have in this thing, and I have always had it. When you don't have it, you know.
"The thing again is toughness. (ESPN analyst) Jay Bilas wrote that book, and it's a great book because it's not just that you want to get in a fist fight. There is a certain thing about mental toughness and those 15 or 16 things that you have that you are just tougher at. You understand that preparation makes you tough. That hard work and doing more than what is expected at practice makes you tougher."