The only thing that surprises me about today’s news that has Tony Bennett retiring after 15 years with UVA Basketball is that it’s happening before the season, and not after.

My reporting, beginning in early May, with a Freedom of Information Act request for a copy of Bennett’s contract, to learn how much time was left on it, led me, over the course of that and several additional FOIA requests, for copies of the employment contracts of Bennett’s staff, to believe that the end of the Bennett era was near.

Timeline: Tony Bennett retirement

• UVA Athletics is making me FOIA the details of Tony Bennett’s contract status (May 6, 2024)
• UVA releases details on length of Tony Bennett contract, answers question on extension (May 13, 2024)
• Tony Bennett has two years left on his contract: What does this mean for UVA Basketball? (May 14, 2024)
• Is there a coach-in-waiting at UVA? Our latest FOIA request tests the theory (May 17, 2024)
• Sanchez, Williford contract language appears to spell out Bennett departure from UVA (May 21, 2024)
• UVA’s Carla Williams, Tony Bennett decline to comment on Bennett’s contract status (May 23, 2024)
• Public-records requests update: Full picture of Tony Bennett’s staff via contract language (June 3, 2024)
• UVA announces hoops coach Tony Bennett signs extension through 2030 season (June 13, 2024)
• Offer sheet from UVA Athletics to Tony Bennett sheds light on when extension was offered (July 2, 2024)
• What you need to know: Breaking down the Tony Bennett UVA contract extension (July 3, 2024)

Now, no, no way did I think it would be over just a few months later; I thought Bennett would coach this season, giving more of the reins to his top assistant, Ron Sanchez, before stepping down in April to hand the program over in its entirety to Sanchez.

I was always under the assumption, even as I was being derided by the rest of the UVA media as being “fringe,” that the contract extension signed by Bennett on June 13 was window-dressing, aimed more at placating the season-ticket base, donors and prep recruits in the next couple of classes than anything else.

The word that had gotten back to me over the summer was that Bennett was already acting more like a CEO behind the scenes, ceding control of the day-to-day basketball stuff to Sanchez, and that it was Sanchez who was the point man on landing the solid transfer-portal class in May.

As I reported back in the spring, Sanchez, who returned to Virginia in the summer of 2023 after a five-year stint as the head coach at Charlotte, was working under a contract that you could interpret as having him as the head coach-in-waiting.

Sanchez’s contract ran through the end of the 2026-2027 season, while the contracts for Bennett and another top assistant on the staff, Jason Williford, expired at the end of the 2025-2026 season.

My reporting on that, and my connecting-the-dots suggesting that Sanchez was the head coach-in-waiting, was what got me that “fringe media” label.

It’s clear now that Sanchez was, at least to Bennett, the head coach-in-waiting, dating back to when Bennett lured Sanchez back from his head-coaching job two years ago.

Now, my thinking about how the transition would go is that Bennett would play out this season in a CEO role, akin to the role that Mike Krzyzewski played at Duke as the transition to Jon Scheyer was working out there over Coach K’s final couple of years in Durham.

I’m speculating here on this next point, but what I think would have changed things here is not necessarily just a change of heart on the part of Bennett about wanting to be around the game of basketball anymore.

The first thought that came to mind with the October Surprise was Dean Smith, who announced his retirement at North Carolina after 36 seasons, effective immediately, on Oct. 9, 1997, so that his long-time top assistant, Bill Guthridge, could get the job.

Smith, quite gentlemanly, handed Guthridge a loaded Final Four team – remember Vince Carter and Antawn Jamison? – and Coach Gut, as he was known to Carolina fans, would lead UNC to another Final Four, in 1999-2000, before he retired after that season.

A call from a former UVA Basketball assistant coach after the news dropped reminded us that Dick Bennett, Tony’s father, stepped down at Wisconsin on Nov. 30, 2000, leaving the job, on an interim basis, to Brad Soderberg, a familiar name to UVA fans, because he served on Tony’s staff for 10 years.

Dick Bennett was 57 when he retired in 2000.

Tony Bennett is 55 years old today.

Soderberg ended up getting passed by for the Wisconsin job on a full-time basis after the 2000-2001 season in favor of Bo Ryan, who went on to win 364 games and lead the Badgers to two Final Fours in his 15 years as head coach.

In that case, Dick Bennett wasn’t able to hand the job to a hand-picked successor, but it still worked out, in the end.

It’s not guaranteed that Tony Bennett will get his guy long-term, either. The gamble on his part is that the team he is handing over to Sanchez will be what I think it will be – a team that will win in the area of 23-25 games, compete for the ACC regular-season title, and play into the second weekend, at least, in March.

If this season goes anything like that for Sanchez, he’s the guy going forward.

If Tony had stayed on as a CEO coach, and the team would end up meeting those expectations, Sanchez doesn’t necessarily benefit from that, is the thinking.

I’ve been beating around the bush on this last point for the last several paragraphs, and I need to get to it.

I referenced that I assume something might have had to change to get Bennett to speed up his departure.

Again, just speculation here, but it’s possible that Bennett has come to learn something in recent days that made him think Carla Williams, the AD, would want to conduct a nationwide search were Bennett to step down after the season, with plenty of time to contact and vet potential candidates and get somebody of her choosing in place.

In this line of thinking, Bennett, by stepping down before the season, as was the case with Smith at UNC in 1997, is making it so that his guy is running for the office as the incumbent, with the incumbent’s advantage.

I’m still beating around the bush here, but the thinking from me is, Bennett doesn’t want to leave the future of the program that he breathed back to life over the past 15 years to Carla Williams, who doesn’t have the best track record with coaches in the money sports.

Think back deep into UVA sports history, and in terms of coaches who deserved the chance to pick their successors, we’re talking Terry Holland, who wanted Dave Odom, and ended up getting his second choice, Jeff Jones, whose run flamed out; George Welsh, who didn’t get any of his guys, and was replaced by Al Groh, whose NFL cache never did work at UVA; and Debbie Ryan, whose top protégé, Dawn Staley, is the best coach in the women’s game, but at another school, South Carolina.

Gurthridge was a placeholder at Carolina, which turned to Matt Doherty after Coach Gut retired, and then had to have Smith beg Roy Williams to leave Kansas to fix the Doherty mistake.

Scheyer is working out well at Duke, though we’re early into the returns down there.

Bennett-to-Sanchez, of course, is no guarantee, as nothing is life is guaranteed.

But Tony Bennett has earned the right to have his guy follow in his footsteps.

I think, I’m damn sure, based on what I’ve known since my FOIA work in the spring, that this is what we’re seeing going on here.