In an emotional press conference announcing his retirement on Friday, former Virginia Cavaliers head coach Tony Bennett didn’t mince words on his reasons for retiring from college basketball, just three weeks before the season was set to tip.

“I’m no longer the best coach to lead this program in this current environment,” Bennett, 55, said.

In a vacuum, his announcement Thursday wasn’t entirely a surprise. Rumors had swirled for years that he might step down earlier than his age and level of success would indicate. The timing, however, was a shock.

And he’ll leave a void at Virginia and in the college basketball universe. This is, after all, the coach who led the Cavaliers to their first and only national title in 2019, a year after losing to 16-seed UMBC in the greatest upset in college basketball history. He hadn’t won an NCAA tournament game since that national title, yet he was regarded as one of the top coaches in the sport.

Just last week, he spoke at ACC media day about the upcoming season and the benefits of adding Kyle Guy, a start on the 2019 national title team, to the staff. He’d also discussed his uncertainty with the new realities of the sport, realities he did not seem to enjoy.

“I always have said, when you’re doing this … you have to be true to yourself and really look at it and say, who am I? Can I operate how I want and can it be successful enough? And you get to choose if you wanna be a part of it or not,” he told ESPN. “And when you feel it’s time, like Jay did, like Coach K, maybe Saban, it’s their choice. And you can sit here and complain and gripe. Or you have a decision to make. Either you try to do it in your way or you get to make that decision.”

A week later, Bennett said he had decided he could no longer serve the Virginia program in the way he wanted.

“I think it’s right for student-athletes to receive revenue. Please don’t mistake me,” Bennett said Friday. “The game and college athletics is not in a healthy spot. It’s not. And there needs to be change and it’s not gonna go back. I think I was equipped to do the job here the old way. That’s who I am.”

As the game rapidly shifted, it became clear teams like Bennett’s Virginia — built on the development of young talent who would stay on campus for three or four years and give the program a continuous set of veteran anchors — would have to shift their mindsets to win big. In the era of NIL compensation and increased transfer portal movement, winning consistently is more difficult now than it was when three returning players (Ty Jerome, Kyle Guy and De’Andre Hunter) fueled a run to the 2019 national championship.

Bennett said he didn’t feel the desire to learn to coach a different way. He also said Friday that he wanted to leave the program to someone he trusted: Ron Sanchez, who was part of Bennett’s staffs at Washington State and Virginia, with a successful stint as head coach at Charlotte from 2018 to 2023..

“They’ve carried me through this transition — the way they think, how they relate, the way their minds are in this landscape, is what’s needed,” Bennett said of Sanchez and fellow associate coach Jason Williford. “And so I’m so grateful. And I just want it to go so well for these guys.”

As a new era begins for the Cavaliers, ESPN’s Myron Medcalf and Jeff Borzello break down what’s next for the school, its players and the sport.

What legacy does Bennett leave behind?

Medcalf: He won Virginia’s lone national title, and that’s significant for any coach. That national title run not only gave Virginia a fresh slate on the basketball court, it changed the perception of the entire university. The Cavs became more than the 1-seed that lost to 16-seed UMBC in 2018.

There are multiple coaches in this game with long careers who won a single national title (Tom Izzo, Jim Boeheim, John Calipari) that elevated their legacies. Bennett will similarly go down as a legend, and it’s not a wild concept to envision Virginia memorializing his contributions with a statue or another gesture. He’s that important to the program’s history.

Borzello: Besides the national championship, Bennett will be most remembered for his style of play — and his unflinching loyalty to that style of play. During Bennett’s tenure, Virginia played some of the slowest, most deliberate basketball in the country, never ranking higher than No. 316 nationally in tempo (and that came in his first season in Charlottesville). In the past four seasons, they were Nos. 357, 357, 360 and 362, respectively.

They were truly elite defensively, too. From 2012-2020, Virginia ranked outside the top-10 in adjusted defensive efficiency at KenPom just once — when they finished 25th. Bennett recruited to that style, he found players he thought could fit what he wanted to do on the court, and then he developed them. After a couple of early NCAA tournament exits, and the UMBC loss, there was widespread criticism that Virginia couldn’t win big in March with that style of play. Did Bennett change? Nope. He doubled down and won the national championship.

What will be the first order of business for Sanchez?

Borzello: Keep the roster together. NCAA rules state players have 30 days following a coaching change to enter the transfer portal. Virginia’s players likely would need a waiver to be eligible at their next school (or at the very least wait until the semester ends), but they could also leave and redshirt this season at a different school, regardless of the waiver process. Virginia was picked fifth in the ACC preseason poll released on Wednesday; plenty of high-major schools would have interest in the Cavaliers’ players, were they to enter the portal.

Medcalf: Considering the season begins in three weeks, there is no time for Sanchez to go off-script — and it won’t be necessary. Sanchez spent lengthy stretches on Bennett’s staffs at Washington State and Virginia, so there will be continuity and familiarity … as long as the players decide to stay. That is no guarantee, but the bonds on Bennett’s staff should help the program avoid the chaos most teams would endure if their longtime head coach had decided to retire less than three weeks before the start of the season.

I think Sanchez’s first press conference will be impactful. He’s known within the Virginia community, but not necessarily to the larger college basketball community, despite a five-year head coaching stint at Charlotte that ended with a CBI championship in 2023. Sanchez is close to Bennett and I’m sure feels a particular loyalty to him because of the impact he has had on Sanchez’s career. But I also think it’s important for Sanchez to convey that the program is in good hands.

He’s going to have to balance his respect for Bennett and the acknowledgement of a new era — one that has to include Virginia accepting the demands of NIL and transfer portal chaos. There is no other way to compete in this current landscape. Sanchez has to make that clear when he’s officially introduced as the interim head coach.

What is the biggest challenge for Virginia without Bennett at the helm?

Borzello: Although the Cavaliers haven’t been a Final Four or title contender over the past few seasons, these are still fairly sizable shoes to fill. Bennett led them to a national championship and six ACC regular-season titles — including in two of those recent “down” seasons. These are the standards Bennett set.

Stylistically, Sanchez is likely to continue Bennett’s slower, more defensive style. During his time at Charlotte, the 49ers were consistently toward the bottom of the league in possessions per game, ranking next-to-last nationally in tempo in his final season — slower than even Virginia. The roster was built with that style in mind, so it shouldn’t be an issue for this season.

Coaches around the ACC have also said Bennett was one of the better head-coach recruiters in the league; once he became involved in a recruitment, he was difficult to beat. Will Sanchez have the same impact on the recruiting trail? And if the school opts to hire someone else as the permanent head coach in the spring, there likely needs to be a roster overhaul.

Why are more coaches exiting the sport amid the massive changes that have altered the game?

Medcalf: Not long ago, I talked to a coach who told me that he’s no longer a head coach, just a general manager. The responsibilities on the shoulders of college basketball coaches have multiplied in recent years. It’s not just about athletes’ new freedom of movement or benefits available to them, either. Those changes have also increased the energy it takes to both recruit and retain a team. Coaches have always had a hand in fundraising, but those efforts are nonstop now. The constant turnover via the portal is an incredible challenge, too.

Coaching in 2024 is a tiring, arduous experience in ways it wasn’t just five years ago. It just feels like fewer coaches — especially those who’ve made seven figures for a long time — will stay past 65 or 70 considering the grind this job now demands.