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

That night, Tony Bennett finally banished his March demons, including the first-ever 16-on-1 upset loss to UMBC last season, and climbed to the top of the mountain in college basketball. The Cavaliers had been excellent for nearly a decade and had finally gotten the validation of a championship. If you had 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 evening is officially recognized as the site of the final March Madness victory of Bennett’s coaching career. The 55 year old is retiringeffective immediately, just two weeks and changing 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, as well as the leader of the 2019 national title team.

Bennett leaving the game on the younger side isn’t a big surprise. Sources throughout the industry had long believed that Bennett, along with Jay Wright, Mike Krzyzewski, Jim Boeheim and Roy Williams as high-profile coaches, could leave the game sooner rather than later. His slow, methodical style of play and focus on player development weren’t a perfect fit for the 2024 version of college basketball, and Bennett had been slow to adapt to some of the changes in the sports landscape. Bennett will discuss his decision further in a press conference on Friday, but it’s hard to imagine he enjoyed working his way through the transfer portal this spring to reassemble his roster or spending time on the phone with NIL agents to sealing the deal on recruiting rather than players and their parents.

However, for him to do so so abruptly, just two weeks and before the start of a new season, is a major shock and a move that has caused a stir throughout the college basketball world. While some feared that such early retirement could be due to possible health problems, Sports Illustrated‘s Pat Forde confirms There were no medical reasons that contributed to his decision to step down. Perhaps the best analogy for the situation came in 2015 with longtime Wisconsin coach Bo Ryan, who first announced his plans to retire after the season in June and then abruptly in mid-December, 12 games into the season gave up. In this case, top assistant Greg Gard took over, earning Wisconsin an NCAA Tournament berth and securing the full-time position. Coincidentally, Ryan was Bennett’s father Dick’s successor in Wisconsin and Tony Bennett’s mentor and boss. Could part of Bennett’s thinking be the hope that this prepares his successor, likely top assistant Ron Sanchez, for the boss job in the same way Ryan did Gard?

It takes a lot for the son of a coaching star like Bennett to step out of this shadow. Bennett did that and more. He succeeded his father at Washington State, where he recruited Klay Thompson and lifted a struggling program to two 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 last seven seasons. Bennett didn’t just win 20; He regularly pushed toward 30 and reached that elite standard four times in his first ten seasons. The Virginia Pack Line became the standard for elite defense in college basketball, giving up the fewest points per game once in six of seven seasons from 2014 to 2020. His defense stunned Hall of Fame coaches like Krzyzewski and Williams and helped build an ACC dynasty in Charlottesville.

He did all of this while also being one of the sport’s true masters, an embodiment of the type of leader every school would want at its side. In both appearance and demeanor, Bennett sometimes seemed more like a basketball professor than a coach. He spoke softly, calmly, thoughtfully, and was as gracious in defeat as he was in victory. The way he handled the UMBC loss may have been his defining moment as a coach and leader; perhaps even more so than the redemption story of the following year. The respect that others in the coaching profession had for Bennett was matched by few modern college coaches.

But Bennett’s program faltered somewhat in the years following that title breakthrough. Part of that NCAA Tournament drought was bad luck: UVA struggled with a COVID-19 outbreak before a first-round loss to Ohio in 2021 and gave away a win against Furman in the first round of 2023 because of a loud prayer. Even a reversed result in these two games would not make this five-year period a success. The Cavaliers’ offense has been stagnant, with just one top-50 unit per KenPom in the last five years, following six straight top-50 finishes at the height of the program’s dominance. Bennett’s last game at Virginia, a 25-point loss to Colorado State in the First Four in which Virginia scored just 14 points in the first half, clearly showed how far the Cavs were from restoring national title standards. Bennett had promised changes to the program’s offensive identity starting this season, which included telling recruits about plans to increase the pace after they were long considered one of the slowest teams in the sport. Instead, he will walk away before these plans can be seen through.

Bennett’s teams could be a difficult proposition at times for the casual fan. Starting a game in Virginia after watching the NBA could almost be whiplash-inducing and at times resemble two different sports. Beautiful or not, Bennett’s methods worked and were the ultimate testament to his unique approach that April night in Minneapolis. Bennett was content to do things his way until the end, and without him the sport is even worse off.