Tony Bennett Signed An Extension Through The End Of The Decade—And Then Retired Four Months Later

For 15 years, Tony Bennett served as head coach of the Virginia Cavaliers men's basketball team. His squads were often defined by their tenacious defense—you typically weren't seeing a lot of made baskets if Virginia was one of the teams on the floor. The school also propelled several athletes into the NBA, including Malcolm Brogdon, Trey Murphy, and Sam Hauser. 

Perhaps most memorably, Virginia became the first No. 1 seed to lose to a 16-seed in the NCAA Tournament, falling 74-54 to the UMBC Retrievers in 2018. The following season, the school returned to the NCAA Tournament—this time winning it all.

However, as college basketball evolved and things like name, image, and likeness deals became more prevalent, Bennett realized he didn't enjoy where things were headed. Despite signing a contract extension this June that would keep him at Virginia at least through 2030, he abruptly announced his retirement on October 18. The school's season begins on November 6.

"The hardest thing to say is when I looked at myself, and I realized I'm no longer the best coach to lead this program in this current environment," Bennett said at a press conference. 

Bennett cited the pressure of winning at a major university as another factor, saying there's a point where "winning is a relief more than a celebration and losing sticks with you, and it's a pain." He also added that he believes student-athletes should receive revenue, but "the game and college athletics is not in a healthy spot." 

Bennett first thought about retiring last season, though he instead worked with the university to restructure his contract. Now, the question is, what happens with that deal? 

Last season, Bennett made $4,021,787 in salary. His contract extension reportedly offered no change in base salary but would include 5% annual raises, continuing the terms of his existing contract. 

Let's do a little math. Assume Bennett's salary from last year got a 5% increase this year and continued at that rate each subsequent season. Over the next six seasons, he'd earn $28,723,635. 

Upon signing the extension, Bennett's contract also stated he'd get another year if he remained in Charlottesville through 2026. So, really, he could have made $34,382,693 in seven seasons.

Now, he could be giving all of that up, though it's possible the school is offering him a nice retirement package. Bennett had a buyout last season worth about $9.32 million—perhaps that ends up being the number the two sides settle on?

Chances are, Bennett will not get all of what he was owed for the next six seasons, but he's okay with that. He's already made millions in his coaching career and can spend more time with his family. Plus, he's leaving the university in the hands of Ron Sanchez, an assistant he trusts.

College basketball is changing. Some coaches hang on for too long. Bennett knew just the right time to ride off into the sunset.