He's helped them learn to "enjoy the ride," to maintain just a little bit more on an even keel through the ups and downs of a long season. He's shown them that putting players first can lead to the kind of program success expected at UK.
But try as he might, Coach Cal knows there's no changing the Big Blue Nation when it comes to Louisville.
"People grieve for a year after the game," Calipari said on the eve of a Sweet 16 matchup with the Cardinals. "People celebrate for a year after the game. I've tried to not make it bigger than it is. But it doesn't work."
It doesn't work because the rivalry is too ingrained. Just ask Jarrod Polson, who grew up a UK fan before going on to a four-year career playing for his favorite team.
"I was born to hate Louisville," Jarrod Polson said, only half joking.
Those are the feelings at play on both the blue and red sides of a Sweet 16 showdown between UK (26-10) and Louisville (31-5). On Friday at 9:45 p.m., bragging rights will be decided. Coach Cal knows better than to think he can control any of that, but it's another story with his team.
"We will not make this game bigger than it is," Calipari said. "It's an NCAA Tournament game. We've gotta play a basketball game against a really good team. Every team still standing is playing a really good team. So that's my message. Don't make it bigger than it is. Just play."
To that end, Coach Cal has given very specific directions to the Wildcats.
"Don't watch any TV," Calipari said. "Watch the History Channel, watch Biography, watch the Military Channel, watch movies and don't read anything, don't look at anything. It has no bearing on this game we're about to play."
That's not a difficult message to put into practice because, really, how could there be anything bigger than playing in the NCAA Tournament? No matter the opponent, there are only two options at this stage of the season: win or go home.
"I don't want to disrespect the rivalry or anything, but we're playing for something bigger than the rivalry," Willie Cauley-Stein told reporters in UK's locker room, television tuned to CNN.
Taking his turn after Kentucky's time with the media was up, Louisville star senior Russ Smith was asked about the way Cauley-Stein views the game. Though he has a couple years and a few extra games of UK-U of L experience on most of the Cats, he agrees.
"It is a rivalry game," Smith said. "There's no way around it. But at the end of the day they're right, it's much bigger than a rivalry. It's a Sweet 16 game. They would have to play with the same enthusiasm and wake up reading the same scouting report as if they were playing a UCLA in the Sweet 16 or UConn. It's just the same game face.
"You just want to get to the next round. And that's what's most important. I feel the same way. I felt the same way the last two, three years, coming into this program, be prepared for every team the same way."
Count U of L head coach Rick Pitino -- a man intimately familiar with the rivalry -- in the same camp.
"I've been in the state 20 years, and the game to me has really only had difficult consequences for the loser twice," Pitino said. "Once was two years ago when they stopped our run in the Final Four, and the next game we play."
Polson is the only scholarship Wildcat who was in uniform for that national semifinal matchup. When he stepped into the Superdome in 2012, he remembers all thoughts about the rivalry -- long as he's been on the UK side of it -- going out the window.
"I mean, in that Final Four game, to me and our team, two years ago it didn't really seem like a rivalry at all," Polson said. "Once you get so far in the tournament there really is no rivalry games. It's just getting to the next round. That's how we saw it back then and I think that's how we're looking at it this year."
Three months ago, the Cats and Cards faced off when the rivalry was the biggest thing at play. Then, UK picked up its signature regular-season win in Rupp Arena, 73-66.
"Honestly, I don't even remember the first game, the first time we played them," Cauley-Stein said. "You know, the only thing I can really take from that is we fought for the whole 40 minutes of the game and that's what we have to do tomorrow, is just play like we played against Wichita (State), which we didn't even realize how close we were to winning or losing the game until the buzzer."
In defeating Louisville, the Cats played with the kind of 40-minute intensity that's become their hallmark in the postseason. With that, UK has improved by the day since the Southeastern Conference Tournament, making them a far different team than on Dec. 28.
"I think we just all settled down and just started thinking about having fun and it's still basketball," Aaron Harrison said, explaining UK's improvement. "We just go out there and have fun and fight for each other."
In a battle of Louisville's experience -- four starters played key roles on last year's title team -- and UK's youth, that carefree approach could work in the Cats' favor.
"The difference between freshmen is freshmen are going to play hard no matter what," Smith said. "That's what's so scary. Freshmen, regardless of how prepared they are, regardless of how trained they are, they're going to always be ready to play and they're always going to come play hard. They may not do the right things, but they're always going to be ready to play."
Differently comprised as UK and U of L may be, their goals -- and their approach to facing their archrival in the tournament -- are the same.
"The goal is to get to the Elite Eight," Smith said. "If you let the university or the other school that you're playing against get in the way of that it could potentially become a problem."
"We're playing to move on and that's the way we're coming into the game," Cauley-Stein said. "We're not thinking about, 'Oh it's Louisville so it's a must-win because it's Louisville. It's a must-win because we're trying to win a national championship."
To bring you more expansive coverage, CoachCal.com and Cat Scratches will be joining forces for the postseason. You can read the same great stories you are accustomed to from both sites at CoachCal.com and UKathletics.com/blog, but now you'll enjoy even more coverage than normal.