Monday night’s final NCAA tournament game between Kentucky and Kansas has particular significance for Kentucky Wildcats head coach John Calipari. (CHRIS KEANE/REUTERS)

But whatever the University of Kentucky coach and his fans may be saying, the final game in New Orleans matters plenty, and will shape his legacy. Calipari—a controversial figure in college basketball at a demanding blue-blood basketball school—may not need a championship ring to prove to himself he is a good coach. With one of the top winning percentages in the sport, a cast of players who are expected to go first or early in the NBA draft, and three Final Four appearances with three different teams (even if two of them were “vacated”), Calipari has done far more than many with his career.

Still, a win in Monday’s title game will be necessary to prove himself to everyone else. That includes the University of Kentucky, which is accustomed to winning basketball tournaments and expects his multi-million contract—the highest in the sport—to pay off. It includes NBA owners, who are surely eyeing how Calipari’s stock rises and falls based on Monday’s result as they consider him for open professional coaching jobs.

And it includes the many fans who question Calipari’s approach to coaching: He may be able to recruit one-and-done players who bring raw talent to the game, but he hasn’t yet made the case that he can mold them into a team that wins it all. If he can’t do it with this team, which includes defensive star Michael Kidd-Gilchrest and “transcendent” likely No. 1 pick Anthony Davis, when can he? Winning a championship might not shut up his critics, but it should hush them for a spell. Calipari will finally have some solid defense against those who say his team seems more like a stopping point on the way to the NBA than a true college basketball program.

Leaders in every field face contests, milestones and tests that define their careers. Some are less public or less objective. CEOs face earnings season. Nonprofit directors face fundraising initiatives and metrics of how efficiently they’ve spent what they’ve raised. Leaders of government agencies must navigate new administrations and implement reforms. Everyone can explain away underperformance by saying that their actions will pay off in the long term, or that they’re being judged by the wrong yardsticks, but that usually does little more than buy them some time.

In fields where the contest is extremely public and definitive—a championship tournament, say, or an election season—leaders have even less power to keep the Ws and Ls from shaping their legacies. In order to relieve the pressure, Calipari is right to try to convince himself that Monday’s game doesn’t matter as much as everyone says it does. And his supporters are probably correct that if he doesn’t do it this year, he will in the future. But in a game where the results are win or lose, success is black and white, and a coach is as controversial as this one, adding a tournament win matters very much for Calipari’s legacy, indeed.

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