After his news conference, he took even more questions in a one-on-one interview with CBS Sports, getting into the specifics of his exit.
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He gave retirement serious thought in the days following Virginia's 67-42 loss to Colorado State in the First Four — I can now share that Bennett talked about this with me off the record in April — but before he could really allow himself to push through on that, recruiting in the portal pulled him into the next phase of the job, and then the next. He didn't want to be pulled any more.
This week, he broke free.
Bennett could have had another decade of good-to-great coaching in him if he felt it. But that feeling sapped from him in recent months, and in just the past week, the epiphany hit. With three days to get away, Tony and his wife, Laurel, headed out of town to Tides Inn, on the Rappahannock River. Over the course of 48 hours, he faced his truth. He said it hit him in a way that was inescapable.
"We lost a lot of players that I think we wouldn't have lost [before NIL regulations]," Bennett said. "And that's OK because it's a new model. And so you've got to decide, where's the line, how far can we go? … It's confusing. I'll be honest, it's confusing.
"I realized if we can't have the right players to compete, the gap could grow," Bennett added. "I felt I was the one holding them back."
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"Now that I'm not in it, I can say this. It's too much," Bennett told me. "You go from the moment the season ends, you're trying to fill your roster and you're in there and you gotta go, go, go. You gotta be on campus. And the season's long enough, whether you are in the tournament, the moment it ends you're right away trying to rebuild your roster, and you're in there, and it was two months of insane work. You're just going, going, going."
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I asked Bennett about why retiring now was appropriate. The offseason is over. The time coaches cherish the most — the actual games — is upon us. He could have privately decided to retire come March 2025 and kept to himself.
"It wasn't like I got this set and I planned this date," Bennett said. "If you're battling things and you're not all in and have the passion to give. You have to know who you are, and you have to be all in with everything. If you know you're fighting yourself in this — because you're still recruiting, you're still involved with stuff — you're gonna have to keep building, and you're always worrying about what's next. And I felt, even in the fall, I felt things I haven't felt for a long time, or maybe I've been battling and coaching some of my perspective. Sometimes, you know, my anger — and people say, 'Oh, you don't get angry' — but I felt myself becoming a little more transactional in mindset. At times. And then I'd catch myself, but I felt that battle being waged inside, and I never want to be like that. That's why I'm not equipped for this."
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He's going to lobby for a true shutdown period in the offseason — if not two — where coaches are mandated to not have any contact with recruits, to enable more balance. Without it, he knows more accelerated retirements are guaranteed in the next few years. He wants to be an agent for positive developments in college athletics. Taking into account the money that's now flowing across high-profile college sports, Bennett sees a major mental health crisis coming for college athletes if more protections aren't put around them ASAP.
For as much as he has concern there, he also wants to give himself to his family more than he ever has — wife, children and parents. **** and Anne Bennett are 81 years old. He's only gotten to see them once or twice a year in recent years. I remember Bennett calling me on an August morning in 2023 for our Candid Coaches series as he sipped coffee outside next to his mother. He was as chatty then as I've ever heard him.
"I don't want to live with regrets," he said Friday.