April 8, 2019. The night the Virginia Cavaliers completed one of the most remarkable turnaround seasons in sports history with their first national championship. 

That night, Tony Bennett finally exorcized his March demons, including the first-ever 16-vs.-1 upset loss to UMBC the previous season, and ascended to the top of the mountain in college basketball. The Cavaliers had been excellent for the better part of a decade, and now finally had the validation of a championship to go with it. Had you suggested to anyone in the confetti-lined building that night that Bennett wouldn’t win another NCAA tournament game in his career, they wouldn’t have even acknowledged it as a possibility. 

More than five years later, that night officially goes down as the site of the final March Madness victory of Bennett’s coaching career. The 55-year-old is retiring, effective immediately, just two weeks and change before the start of a new college basketball season. Bennett retires as the winningest coach in Virginia history, a two-time National Coach of the Year and six-time ACC champion, in addition to the leader of the 2019 national title team. 

Bennett walking away from the game on the younger side isn’t a huge surprise. Sources throughout the industry had long believed Bennett could join the likes of Jay Wright, Mike Krzyzewski, Jim Boeheim and Roy Williams as high-profile coaches to walk away from the game sooner rather than later. His slow, methodical style of play and emphasis on developing players weren’t perfect fits for the 2024 version of college basketball, and Bennett had been slow in adapting to some of the changes to the sport’s landscape. Bennett will further address his decision in a news conference Friday, but it’s hard to imagine he enjoyed having to scrape through the transfer portal to rebuild his roster this spring or spending time on the phone with NIL agents to seal the deal in recruiting rather than players and their parents. 

However, him doing so this abruptly, just two weeks and change before the start of a new season, is very much a shocker and a move that sent reverberations throughout the college basketball world. While some feared such an early retirement might be due to potential health issues, Sports Illustrated’s Pat Forde confirmed there was nothing medical that contributed to his decision to step away. Perhaps the best comparison for the situation came in 2015 with longtime Wisconsin coach Bo Ryan, who initially announced in June his plans to retire following the season and then walked away abruptly in mid-December, 12 games into the season. In that instance, top assistant Greg Gard took over, lifted Wisconsin to an NCAA tournament berth and earned the full-time head gig. Coincidentally, Ryan was the successor to Bennett’s father, Dick, at Wisconsin and a mentor and boss to Tony Bennett. Could part of Bennett’s thinking be the hope that this sets up his successor, likely top assistant Ron Sanchez, for the head job in the same way Ryan did with Gard? 

It takes a lot for the son of a coaching star like Bennett to step out of that shadow. Bennett accomplished that and more. He took over for his father at Washington State, where he recruited Klay Thompson and elevated a moribund program to a pair of 26-win seasons in three years. He then brought his father’s patented “Pack Line” defense with him to Virginia, where he inherited a program that had won 20 games just once in the previous seven seasons. Bennett didn’t just win 20; he regularly pushed toward 30, hitting that elite standard four times in his first 10 seasons on the job. The Virginia Pack Line became the standard for elite defense in college basketball, at one point giving up the fewest points per game in six out seven seasons from 2014 to ‘20. His defenses baffled Hall of Fame coaches like Krzyzewski and Williams and helped create an ACC dynasty in Charlottesville.

He did all that while being one of the sport’s true gentlemen, an embodiment of the type of leader any school would want on its sideline. Both in appearance and demeanor, Bennett sometimes came across more like a basketball professor than a coach. He was soft-spoken, calm, thoughtful and as gracious in defeat as he was in victory. The way he handled that UMBC defeat may have been his defining moment as a coach and leader; perhaps even more than the redemption story of that following year. The respect others in the coaching profession had for Bennett was rivaled by few if any modern college coaches. 

But Bennett’s program did slip some in the years following that title breakthrough. Some of that NCAA tournament drought was bad luck: UVA dealt with a COVID-19 outbreak before its first-round loss to Ohio in 2021 and gave away a win against Furman on a buzzer-beating prayer in the first round in ‘23. Even a flipped result in those two games wouldn’t make this five-year period a success. The Cavaliers’ offense sputtered, with just one top-50 unit per KenPom in the final five years after six straight top-50 marks during the peak of the program’s dominance. Bennett’s final game at Virginia, a 25-point loss to Colorado State in the First Four during which Virginia scored just 14 first-half points, truly exposed just how far away the Cavs were from re-establishing that national title standard. Bennett had promised shifts to the program’s offensive identity starting this season, which included telling recruits of plans to pick up the pace after long ranking as one of the slowest teams in the sport. Instead, he’ll walk away before those plans can be seen through. 

Bennett’s teams could be a hard watch at times for the casual fan. Turning on a Virginia game after watching the NBA could be almost whiplash-inducing, resembling two different sports at times. Thing of beauty or not, Bennett’s methods worked, that April night in Minneapolis the ultimate validator of his unique approach. Bennett was happy to do things his way until the end, and the sport is worse off without him in it.