Tony Bennett’s legacy a case study in the madness of March

Mamadi Diakite’s shot to force overtime against Purdue in the 2019 Elite Eight — set up by a wacky series of bounces and a heads-up pass following a missed free throw — is the difference between Bennett being known as a college basketball legend and one of the sport’s most notorious chokers. The Cavaliers ultimately defeated the Boilermakers and went on to win the national championship the following week. But had Diakite missed that shot, Bennett’s career arc would’ve been forever altered.

Instead of being remembered as a champion, Bennett would be remembered for UVA’s historic loss the previous year to UMBC, when the Cavaliers became the first team to ever lose to a No. 16 seed as a No. 1 seed in the NCAA Tournament. Virginia didn’t just lose that game, either. It got demolished. UMBC beat the Cavaliers by 20 points. And Virginia wasn’t just any No. 1 seed. It was the No. 1 overall team in the bracket, considered by many the favorite to win it all.

It was one of the most humiliating defeats in the history of sports, and if you take out 2019, the rest of Bennett’s tournament record isn’t a whole lot better. He had no additional Final Four appearances and only one additional Elite Eight, in which UVA blew a late 15-point lead to 10th-seeded Syracuse in 2016. Then after 2019, Bennett never won another postseason game in three tournament appearances. Two of those losses were to No. 13 seeds and the third was a First Four no-show in which Virginia scored 42 points.

Of course, it’s not fair to reduce Bennett’s body of work to his team’s fates in the most random postseason format in all of American sports. The madness of March is what makes the NCAA Tournament so special, but let’s face it: it’s a single-elimination bracket that consists of 68 teams. To win it, you have to win six win-or-go-home matchups in a row. Just to make the Final Four, you have to win four of them. It’s extremely difficult and many coaches — even some of the great ones — never do it.

That would be the narrative surrounding Bennett had it not been for 2019. Not that he was one of the best talent developers in the sport. Not that he consistently made his teams nationally relevant with rosters that paled in comparison to what ACC rivals such as Duke and North Carolina boasted on a yearly basis. Not that he turned countless three-star recruits into legitimate NBA prospects. It would be that he always choked in March. That he never really won anything relevant. That he was the guy who lost to a No. 16 seed. 

Just ask Purdue’s Matt Painter about how difficult that label is to shed. Ironically, in this alternate reality in which Diakite’s shot missed, Painter might also be perceived in a much different light. He’d have multiple Final Fours on his resume and perhaps the Boilermakers would have won that 2019 title. Like Bennett, his specialty is taking underrated recruits and developing them into winning players. Yet without a national championship, he’s still known by many for Purdue’s tournament shortcomings.

So while the college basketball world gives Bennett his well-deserved flowers, let’s take a moment to acknowledge the importance of perspective. Bennett isn’t a legend because the ball bounced his team’s way in some close games one year. He’s a legend because he built and sustained a culture of excellence that made UVA one of the most dominant forces in college hoops for the better part of a decade.