Tony Bennett was emotional and candid in saying goodbye to the Virginia Cavaliers and college basketball Friday. And perhaps calculating, too.

Bennett said he didn’t reach this decision to abruptly retire, less than three weeks before Virginia’s opener, until a recent fall getaway with his wife. He acknowledged thinking about it in the spring, when rumors were flying in the sport that he might hang it up. But then he signed a recruiting class, and a contract extension, and said he was excited for the season … until he suddenly wasn’t.

Maybe that’s an honest accounting of how it all went down. But this could be construed as a shrewd move designed to do two things:

Bennett isn’t built for college hoops in the 2020s, a time when athletes have more freedom and a lot of adults struggle with the concept. This was the last act of a coach who craves control.

Bennett’s lack of adaptation to the modern world has little to do with his stodgy, stultifying but largely successful playing style. It’s more related to modern rules and player movement. (It’s less about NIL—he acknowledged that players should be compensated.) 

He’s an old 55 when it comes to the current state of the game, and he freely admitted that Friday. More than any of the other national championship coaches who have retired in recent years—from Jay Wright to Jim Boeheim to Mike Krzyzewski to Roy Williams—Bennett plainly stated that the current state of affairs is driving him away.

He called himself “a square peg in a round hole.” He said his staff “pulled me along” in the new era by handling most of the conversations with players’ agents. He said college athletics “is not in a healthy spot,” and that it needs to “get back to regulations and guardrails. There’s things that need to change.”

NCAA regulations and guardrails have been getting routed in the courts for the past several years, so this yearning for yesteryear might be a losing fight. But there was one battle Bennett could still win, and that was the timing and nature of his retirement.

If he’d retired last spring, the transfer portal would have opened for 30 days for the Virginia players. The Cavaliers’ roster likely would have scattered. That’s the way of the world now. It happens almost everywhere that a coaching change occurs.

Same thing if he’d retired during the summer, or anytime before classes began at Virginia Aug. 27. Even for another month after that, players likely could have transferred and found an immediate spot at a school that is on a quarter system and didn’t begin classes until late September.

Doing it now, smack in the middle of the semester, leaves those players with nowhere to go. That includes five incoming transfers, from Florida State, San Diego State, Kansas State, Duke and Vanderbilt. It also includes two freshmen. They’re pawns in Bennett’s program preservation chess game.

And now Sanchez is in charge of moving those pawns around the board. If Bennett had stepped down in the spring, maybe Sanchez gets the job but maybe not—Virginia athletic director Carla Williams would have been able to make that call and conduct a search, if she so desired. Doing it mere weeks before the season opener forces Virginia to go along with Bennett’s personal succession plan for 2024–25 at least.

This is an ego-and-control play, though he’s hardly the first to do it. It’s a tried-and-true move for basketball coaches who have been successful enough to call their own shot. 

Oct. 9, 1997: Dean Smith retired at North Carolina, gifting the job to assistant coach Bill Guthridge. While winning a lot and taking the Tar Heels to two Final Fours, Guthridge only lasted three seasons before stepping down himself.

Nov. 30, 2000: None other than Dick Bennett, Tony’s dad, stepped down three games into the season at Wisconsin, and seven months after taking the Badgers to the Final Four. He was 57 years old, just two years older than Tony is now. Bennett handed the job to Brad Soderberg, who finished the season but didn’t keep the job. (Soderberg has worked for Tony Bennett at Virginia since 2021.)

Dick Bennett came out of retirement in 2003 to be the coach at Washington State. After three seasons he turned the program over to … Tony Bennett.

Sept. 12, 2012: Jim Calhoun retired at Connecticut, amid some strife and controversy. But after winning three national championships, Calhoun had the clout to hand-pick successor Kevin Ollie. He won a surprise natty in 2014 but was fired by 2018.

Dec. 15, 2015: Bo Ryan, who followed Soderberg as the successor to Dick Bennett at Wisconsin, went to the Dick Bennett retirement playbook. After going to the Final Four the previous season, Ryan announced that the 2015-16 season would be his last and he’d be replaced by assistant Greg Gard. Then Ryan waffled on whether he would retire. Then he did, abruptly, 12 games into the season, and Gard took over.

With those retirements, the players left behind were stuck in place for that season—and then faced a year sitting out if they chose to move to a new school. At least now, Virginia players can participate in 2025–26 at their new school. But they have effectively been held hostage for 2024–25.

(December graduate transfers, if there are any candidates for that on this Virginia team, could play as soon as the spring semester somewhere else. That might be difficult, due to scholarship availability and playing time and rotations being set. But it’s allowable under NCAA rules.)

Bennett is held in universally high regard in his profession and around college athletics. His It’s The System’s Fault retirement at a young age will generate a new spasm of despair over the state of things. Some concerns are justified, but many are exaggerated—and not much is going to change on account of Tony Bennett.

This last act of a coach who craves control is only a win for him and his hand-picked successor. It doesn’t beat back the advancing tide of the new era.