Bennett - dressed in his signature suit-minus-tie look - told those gathered at his exit news conference that name, image and likeness money and the transfer portal have brought elements to the job that he's "not great at."
"I looked at myself and I realized, I'm no longer the best coach to lead this program," Bennett said with athletic director Carla Williams seated next to him. "If you're going to do it, you've got to be all in. You've got to have everything. And if you do it half-hearted, it's not fair to the university and those young men. That's what made me step down."
Bennett famously led Virginia to the 2019 national championship a year after becoming the first team downed by a 16-seed in the NCAA tournament.
He is the latest - and, at 55 years old - youngest high-profile coach to walk away citing a measure of burnout with the modern realities of the profession. That list includes former Villanova coach Jay Wright, who retired two years ago at 60.
"The game and college athletics is not in a healthy spot," Bennett said. "And there needs to be change. I think I was equipped to do the job here the old way. That's who I am and that's how it was. My staff has buoyed me along to get to this point, but there needs to be change."
Former assistant Ron Sanchez, who rejoined the program last season, will take over as interim coach. Williams said a national search for Bennett's replacement will begin shortly, but Bennett is hopeful Sanchez will perform well enough to land the full-time post.
Williams said Bennett told her of his decision on Wednesday morning, though she noted that the two had discussed the possibility at times during the past three years.
"I believe he is equipped to do the job, but as he said to all of you, he has to have his whole heart in it," Williams said, her cheeks still stained with tears shed during Bennett's remarks. "He is the embodiment of humility because he could keep doing this and not have his heart in it, but it takes more courage to say, 'I'm not the person for it.'"
A Process And A Realization
As for the stunning timing of his retirement, less than three weeks before the team's Nov. 6 opener against Campbell, Bennett said he thought seriously about stepping away immediately after the past season concluded with a First Four loss to Colorado State in Dayton, Ohio.
The Cavaliers struggled offensively in that game and haven't won an NCAA tournament game since the 2019 title matchup.
But, because the recruiting calendar required him to immediately go to work evaluating potential transfers, Bennett said he never fully took the time to consider his situation.
He said he was excited about the players the program signed, about the new offense he was installing and about the prospects for the upcoming season. He felt, then, sufficiently energized to sign a long-term extension with Virginia, though he acknowledged it was never likely he would've lasted the full term of the deal, which ran out in six years.
Then, finally, there was a break in his hectic schedule. He and his wife, Laurel, took a trip during UVa's fall break, giving the couple the chance to process and contemplate the future.
"That's where I kind of came to the realization that I can't do this," Bennett said, becoming overcome by emotion. "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."
Bennett's current players and staff stood toward the back of the room Friday, listening as he spoke.
"I'm happy for him," said former player Isaiah Wilkins, now an assistant coach with the program. "I see he's at peace. I think he knows himself well and obviously it's a family decision."
Unparalleled Success At Virginia
With the person who hired Bennett, former Virginia athletic director Craig Littlepage, looking on, Bennett talked about his pride in the way he and his staff built the Cavaliers into one of the nation's most successful programs. Littlepage hired Bennett in 2009 following three strong seasons at Washington State.
After a 15-16 record in his first year at UVa, Bennett went on to post 14 consecutive winning seasons.
He posted a 364-136 mark at the school, leading the program to two ACC championships, six first-place finishes during the ACC regular season and 10 NCAA tournament appearances. Bennett was named ACC Coach of the Year in 2014, 2015, 2018 and 2019.
"I didn't envision, in 15 years, what it would be like," Littlepage said. "I was thinking more in the short term. 'We've gotta get this thing going and knew that would take a couple of years.' ... He had the pedigree. He had the understanding of the college game. He came to understand the University of Virginia in short order. There was no question he was going to have success."
Long-derided by many national media types for his unusually slow tempo of play and defense-first - and second and third - mentality, Bennett's first-round NCAA tournament loss to UMBC in 2018 gave ample fuel to his critics, creating a chorus questioning whether his pack-line defense was built to win championships.
Bennett, in his signature way, handled the loss with grace and promised his heartbroken players that it would be "a ticket to someplace they couldn't go without it."
The following season, after a dramatic run through the NCAA tournament, Bennett and the Cavaliers cut down the nets in Minneapolis, having topped Texas Tech and claimed the school's first national title.
"I've been here for 15 years as the head coach, and I thought it would be a little longer, to be honest, but that's been on loan," Bennett said. "It wasn't mine to keep. This position has been on loan, and it's time for me to give it back."
The Associated Press contributed.