Virginia Cavaliers Tony Bennett An emotional Tony Bennett retired officially as the head coach of Virginia men's basketball on Friday. ~ Photo by Kris Wright/TheSabre.com

Virginia basketball coach Tony Bennett contemplated the state of college athletics many times before, but he thought he could keep pushing on and adapt to the changing landscape. A recent trip with his wife Laurel, however, provided a sense of uncertainty and ultimately clarity that he no longer could.

After wrestling with those thoughts following the University of Virginia’s fall break, Bennett ultimately decided to retire as the Hoos’ head coach. Bennett, who had signed a a contract extension in June, officially stepped down at retirement press conference on Friday morning in the John Paul Jones Arena dining room, the exact location where it all began 15 years ago.

“After the season, I thought about maybe stepping away. Every coach, you get to that. It was a long season. It was a hard ending,” Bennett said. “And I thought about that, but the way the recruiting calendar works, you literally jump in. For two straight months we're in the transfer portal, and you guys know that. You're involved in situations and conversations and things that I'm not great at, but because my staff, because of Coach [Ron] Sanchez, Coach [Jason] Williford, Coach [Orlando] Vandross, all the coaches, all the staff, Coach Zay [Isaiah Wilkins], we got excited. We landed a really good group of transfers. We had two good incoming players. And I was excited about that and going forward. Then I was offered a contract extension, and I signed it. I didn't know if I'd be able to do the whole six or seven years obviously, but I was excited and thought, I think I can do this. I'm excited about the way forward.

“I was encouraged and it excited me for this way forward, and I kind of went through the summer and the fall hoping to do this,” Bennett continued. “I felt some things as it went along, and it really wasn't until fall break that we have here, where Laurel and I went away and just kind of processed about what the future would be. That's where I kind of came to the realization that I can't do this. It's not fair to these guys and to this institution that I love so much to continue on when you know you're not the right guy for the job.” 

The 'this' referred to by Bennett is the combination of things that have changed the dynamics of coaching college basketball. The transfer portal, as mentioned, allows player movement without sitting out a year like in the past. While UVA has benefited from transfers joining the program quickly, it does complicate roster management, relationships, and decision-making for leadership. There's also the matter of the time it requires. The high school recruiting calendar typically opened for a short period in late April, giving a brief moment of respite for coaches, but the transfer portal now opens before some teams have even completed postseason play.

Name, image, and likeness rulings in the legal realm also opened the door for college athletes to profit off of their own popularity and value. The NIL concept in spirit would allow the ability for student-athletes to enter marketing agreements with local businesses, product promotions, clinics, private training, or other ventures due to their recognizable stature in the sports world. In reality, third party collectives - organizations to centralize some of that money - and other avenues turned that idea into the ability to pay players to choose or change schools. While 'pay for play' rules had restrictions from the NCAA level, those rules were essentially unenforcable as different states and groups began to establish their own laws and guidelines. With that came agents and others wanting to represent student-athletes

Throw in legalized gambling, conference realignment, and other stressors on the system as well.

With all of that swirling, Bennett tried to navigate a way forward. Still, he has concerns about the mental health of the student-athletes and the opportunities for the less hyped sports. He said his assistant coaches helped reduce some of the pressures and "buoyed me along to get to this point." That included handling a lot of the negotiations, monetary conversations, and parts of the job that came with the new climate. In the end, though, he noticed his heart and passion wasn't there in the same way. So he made the decision to step away. While some may question how making that choice just before the start of the season fits into the Five Pillars that have been at the core of the program - humility, passion, unity, servanthood, and thankfulness - Bennett said that he leaned into the principles.

"I think about those pillars Carla [Williams] mentioned, and the first two, humility and passion," Bennett said. "Humility means know who you are and have sober judgment, and passion means do not be lukewarm, be wholehearted in all you do. I think those are the ones that caused me at this time to look and have sober judgment about where I was at. That's probably the thing that has choked me up the most and 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, and if you're going to do it, you've got to be all in. You've got to have everything. If you do it halfhearted, it's not fair to the University and those young men. In looking at it, that's what made me step down. There's still a way in this environment. There's a way with Carla and President [Jim] Ryan and the board to do it and hold to our values, but it's complicated. And to admit, honestly, that I'm not equipped to do this is humbling, but it honors the pillars."

Virginia opens its season on Wednesday, Nov. 6 against Campbell. With less than three weeks before that game arrived, Bennett informed UVA Athletics Director Carla Williams and President Jim Ryan. The Bennetts shared a dialogue about his feelings and he decided to stay on course for retirement. Williams said she was not shocked by it given ongoing conversations with Coach Bennett over the past three years.

And while it all happened fast, Bennett said he is at peace with retirement.

"As I said, I didn't have a lot of time to process. There are some things that I went through. I am at peace, and as I said, when you know in your heart it's time, it's time," Bennett said. "Will I miss the game? Do I love the game? Absolutely. But I don't think I'm equipped in this new way to coach, and it's a disservice if you keep doing that. I'm very sure this is the right step. I wish I could have gone longer. I really do, but it's time. I wouldn't have done it if I didn't think we had the right group of young men and the right staff to lead them forward in this way. That was the one thing President Ryan and Carla and Laurel and I talked a lot about, you don't want to have regrets. You don't want to have regrets. Think through this. Sit on this. I think I'd have more regrets staying longer and not being able to be all in and not sure and giving everything to these guys than stepping away with maybe a little more energy in the tank but giving it in the right place. That would be the bigger regret I'd have." 

The timing of Bennett's retirement means Virginia will have an interim coach for the 2024-2025 season. Ron Sanchez, who rejoined the staff as associate head coach last summer after a head coaching stint at Charlotte, will assume that tag. Other than that five-year break on his own, Sanchez has worked alongside Bennett since 2003 when both were assistants at Washington State. The closeness of that relationship has led to some speculation that the timing of Bennett's decision was to insure that Sanchez received a chance at the job. While Bennett did say that he always hoped one of his assistants would get the job, in part because that would mean the program had continued to succeed, he also said Friday that "this was not premeditated" and that he was "hoping to get through" the upcoming season.

However, the trust Bennett has in Sanchez as well as associate head coach Jason Williford, Orlando Vandross, Isaiah Wilkins, and others certainly factored into his belief that he could step away. A reporter asked that question at the JPJ - "How much of the fact that you're leaving the program in what you feel is a good spot influence your decision, give you some freedom maybe to do it? - and Bennett said that he believed in his staff fully and that helped to leave the program in a strong spot.

"[The team has] to gel together and go through stuff, but because of the staff and because of these young men, I'm so hopeful for them. I shared that message with them. That was hard to share with them and the staff, who I care so much for," Bennett said. "I feel it's in a strong spot, and I feel like the support in how it wants to go forward that's aligned with the mission, and what this staff believes and what these players are about give it the best chance. Quite honestly, you just don't know in college basketball what rosters are, what teams have. The staff ... was the one that they pulled me along. They would handle the talks with the agents. They would handle things. I realized, if I'm going to do this, I have to be involved in everything. They made it easy for me, because of how they reacted. And they're forward thinking, they all are, and they have I think the right way. I'm a square peg in a round hole. That's what it is. Maybe that's the hard part to admit, but it's okay because, when you tell the truth, there's freedom in that. That's the reality of it."

Emotional at times during the press conference, Bennett circled back to that theme, the idea that he doesn't fit in the college basketball coaching world right now, multiple times during the day. But he's leaving with gratitude for how his time on the sidelines went.

Reluctant to get into coaching at all initially, Bennett helped build succesful programs at Washington State and Virginia where winning had not been as plentiful in the immediate time before his arrival. He completed his UVA tenure with a 364-136 record and as the program’s all-time winningest coach. He surpassed Terry Holland, who posted 326 victories with the Cavaliers. Counting his time at Washington State, Bennett compiled a 433-169 career record with 12 NCAA Tournament appearances.

At Virginia, his teams won the 2019 National Championship, two ACC Tournament titles in 2014 and 2018, and six ACC Regular Season Championships. Players received first-team All-ACC honors 9 times, second-team All-ACC honors 10 times, and third-team All-ACC honors 9 times in his tenure. Five players were named All-Americans as well. Ten players were selected in the NBA Draft. He came to Virginia to test his coaching merits among Hall of Famers and while he hoped for success, it "was beyond probably my wildest expectations" and "I wouldn't trade it for anything," he said Friday.

Reflecting back, he said all the wins, the tough losses, and the support from the University, the adminstration, and the fans all add up to something memorable and rewarding after 15 years of pouring his heart into it.

"They let us do it. Carla and President Ryan let me do it my way. And, Craig [Littlepage], you did, and Jon Oliver and President [Teresa] Sullivan. President [John] Casteen was here, I think one year, if I'm not mistaken. You guys let me do it my way. Whatever you need, you do it your way, we'll support you. That's rare. Sometimes you can get micromanaged, and you've got to do it this way, that way. I stand on all that," Bennett said. "The fans embraced - most of them. There's always going to be critics. When you're the man in the arena, you're the head of the team, there's always going to be critics. But overwhelmingly, they liked what they saw in terms of you can have it all at Virginia when you're here, and we tried to build that. They were an unbelievable fan base. The faithful ones when we weren't great and the ones we picked up and the support that I've gotten, and I'm grateful, and I'll always have that special place in my heart."

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