Tony Bennett retires: How he guided Virginia from 16-seed loss to winning national championship

Mamadi Diakite grew up in Conakry, Guinea and learned about basketball watching grainy Michael Jordan videos. He didn’t play organized basketball until he came to the United States for high school. He knew nothing about the pomp and circumstance of the NCAA Tournament, of March Madness and brackets and “One Shining Moment” and the legends that are born in March and April.

And so when No. 1 seed Virginia lost to No. 16 UMBC in 2018 — the first 16-vs-1 upset ever — Diakite was in for a surprise.

“I knew it was bad,” Diakite said back in 2019, as Virginia was on its way to a national championship. “I didn’t know how bad it was until we got on the bus and we couldn’t get in the hotel from the front. We had to go all the way back. And that’s when I knew it was really bad.”

He pauses.

“I was ashamed of myself.”

Virginia basketball, in that moment, could have been ashamed of itself, too. The Cavaliers had endured plenty of tough March moments in previous years under Tony Bennett and were already regarded as slow-paced, low-scoring underachievers on the largest stage. But this? There was no coming back from this, right? Virginia players cried. Kyle Guy’s tear-streaked face became the face of the program.

“If you play this game and you step into the arena, this stuff can happen,” Bennett said astutely after the game. “And those who haven’t been in the arena or in the competition, maybe they don’t understand that. But there’s chances for wonderful things to happen, but when you’re in the arena, stuff like this can happen and all those who compete take that on. And so we’ll accept it.”

Bennett’s tenure at Virginia ended suddenly Thursday when the Cavaliers’ all-time winningest coach retired just weeks ahead of the 2024-25 season opener. His legacy is defined by several aspects — the pace and the defense that constricted and enraged, the building of a program from nothing to arguably the ACC’s best program of the 2010s — but none more so than the turnaround from losing to a 16-seed to winning the national championship.

If Guy’s face is what the program was best known for after the defeat, Bennett’s steadfast approach is what helped Virginia accept the loss, endure the aftermath, regroup and ultimately rebuild into a champion. It remains one of the all-time great turnarounds in any sport, and it takes on a new meaning after Bennett’s abrupt departure.

Perhaps Bennett was the perfect steward to guide the ship, in that moment lost at sea. In 2016, Virginia blew a double-digit second-half lead to Syracuse in the Elite Eight, and Bennett resorted to one of his favorite sayings — “Weeping may endure for the night, but joy comes in the morning.” — from the Bible.

So in 2018, Virginia wept, and it wept for more than a night. Guy wasn’t alone, but he was the the face of it. He’d later open up about his struggles with mental health and anxiety specifically.

But then the Cavaliers got to work, fully behind Bennett despite the questions regarding his system and his big-game acumen. Point guard Ty Jerome and Bennett met just three days after the UMBC loss to discuss offensive adjustments. De’Andre Hunter, who had missed the UMBC loss with a broken wrist, returned alongside Jerome, Guy, Diakite, Jack Salt and Jay Huff. Bennett, who had been reticent to use the transfer portal, went out and got Braxton Key from Alabama to provide wing versatility. He also unearthed Kihei Clark, a dogged but undersized Los Angeles-area point guard recruit who wasn’t even ranked by 247Sports.

So the pieces were in place. The motivation was obvious. But the sting was still there, and after an unprecedented, emotional offseason, Bennett needed his team to have an outlet.

So they went whitewater rafting, an experience that thrilled — and, really, terrified — the team. Bennett loved every minute. He had made so many decisions during his tenure on the sidelines at Virginia. But this decision, to take this players miles and miles away from any basketball court, was the perfect one.

“I learned to trust [my teammates and coaches],” Diakite said. “I felt like we were syncing with the coaches. The coaches looked sort of like players. We could interact and have fun. That hierarchy wasn’t here.”

After an offseason in which things could have fallen apart, Bennett not only kept things together but made them stronger. Rafting trips, mini golf and pregame “Name That Tune” sessions — all features that season — hadn’t been on the agenda in the past. But Bennett knew how to pull this burdened group together.

The team motto, he decided, would be “United Pursuit.”

Virginia boat raced through its regular-season schedule, going 28-2 with both losses to Zion Williamson’s Duke team. The Cavaliers kept their slow pace but emerged as an offensive force, posting the second-best offensive efficiency in the nation to go along with the fifth-best defense.

Then came the March worries, again. After being bounced in the ACC Tournament by Florida State, Virginia trailed by 14 points early against 16-seed Gardner-Webb. This time, there was no worry at halftime, when Virginia trailed by six.

“It was a different halftime than last time,” Bennett said. “It was one thing I said to my staff, and we just talked right before we went in there. I said, uplift them, and we talked about don’t panic, but play with fight, because that’s what got them back in.”

The raced past the Runnin’ Bulldogs 71-55 and then stifled Oklahoma, 63-51. Sooner coach Lon Kruger talked about the “fantastic job” Bennett does with his defense, and it was on display in the Sweet 16, when Virginia beat Oregon 53-47.

Then came Purdue. And with a trip to the Final Four on the line, Bennett harkened back to a much less stressful time: the rafting trip.

“I remember just like it was the most beautiful setting just floating down the river with these guys, and I remember saying that in my mind,” Bennett said. “I actually got a little emotional with them. I said, ‘Here we are.’ This was on the verge of the Elite Eight game.

“I’m floating on that river. What’s this year going to bring? Because it’s a significant year, I thought that. I was thinking, ‘Wow, here I am.’”

The Cavaliers and Boilermakers played one of the all-time great NCAA Tournament games. 

Diakite, who had struggled significantly in the ACC Tournament, was the regulation hero. But again, in the background for Diakite’s heroics was Bennett, not necessarily for the strings he pulled on the court, but the tone he had struck in a conversation with Diakite off it weeks earlier.

“I just threw a challenge to myself, in a sense, by telling [Bennett] I got his back, we’ll make it to the final and actually win it” Diakite said. “Telling him made me think about it every night, every day, every second I was working and made me more hungry. I wanted to contribute for every game, and I think I did.”

Bennett, often reserved, couldn’t hold in the emotion when he cut down the nets in front of his father, longtime coach Dick Bennett, and his players couldn’t hold back their praise.

“[For] how many times Coach Bennett has been a 1-seed or a 2-seed and has had so much regular season success, to be the team that gets him to the Final Four, I think that’s what means the most.” Jerome said. “But he’s believed in every single one of us. He has our best interest at heart, on and off the court. And he’s a great person.”

The madness didn’t end in March. On Virginia went to its first Final Four since 1984, when Ralph Sampson roamed Grounds and dominated paints. Again, Bennett needed miracles, Guy’s six points in the final 10 seconds propelling the Cavaliers past Auburn 63-62.

The national championship proved to be another all-time classic. Hunter hit a 3-pointer to force overtime. He made another — using a screen set by Guy, the inverse of what had happened so often that season — to give Virginia the lead for good in the extra session. In a moment that perfectly illustrated Bennett’s humble nature, instead of taking credit for the play call, he admitted he worried he had wandered too far onto the court to deliver instructions.

Key threw down the game-sealing dunk, and the confetti fell moments later: Virginia 85, Texas Tech 77.

The “United Pursuit,” coined by Bennett, was complete, and it took every bit of unity. Clark and Diakite combined on the greatest shot in program history. Guy, Jerome and Hunter delivered huge buckets throughout, each stepping up in crucial moments. Key played 29 minutes in the title game, his most in over two months, and Virginia outscored Texas Tech by 18 in those 29 minutes.

And there in the background was Bennett. As Virginia players and managers celebrated under the confetti, Bennett offered a small smile before turning straight-faced and shaking the hands of Chris Beard and the rest of the Texas Tech staff. Then he hugged his own staff and let a smile return, an understated celebration fit for a person who know how to keep things in perspective.

He was what Virginia needed all along. He didn’t give up on himself, his players, his coaches or his system after historic losses. He reminded them that losses happen, and that wins do, too. And in the process, he delivered one of the all-time great comebacks simply by remaining true to himself.

“Coach Bennett always talks about staying faithful, and he told us don’t grow weary in doing good, and that’s an every-possession mindset,” Jerome said. “It’s a life mindset. Just play till that buzzer sounds. … We all believe in each other, and it’s the most special team I’ve ever been on.”

And when it was Bennett’s turn to speak, he struck the right chord again.

“If you learn to use it right — the adversity — it will buy you a ticket to a place you couldn’t have gone any other way,” he said. “I don’t know, maybe we could have, but I don’t know, going through what we did last year and having to … You know, it helped me as a coach. All the stuff that they talked about, I think, bought us a ticket to a national championship.

“That’s why we said this was our united pursuit. That was our theme, and I loved it, because it was everything we had.”

For 15 years, Bennett held together everything Virginia had, and for one special season in particular, he and his players delivered everything Virginia needed, too.