Brian O’Connor was at home, about to have dinner with his family, when his phone rumbled. One University of Virginia coaching legend was calling another.
“Hey, Brian,” then-UVA head men’s basketball coach Tony Bennett said to his baseball counterpart. “What are you and Dillon doing tonight?”
What ensued was the story that popped into O’Connor’s head following the sudden news of Bennett’s retirement in October.
Beyond the school-record 364 wins, six regular-season Atlantic Coast Conference titles and the 2018-19 national championship were Bennett’s acts of kindness performed far from the public eye – like the time he invited O’Connor and his son, Dillon, to come over and meet Muhammad Ali. The global icon and boxing giant was in Bennett’s neighborhood visiting with Ali’s attorney, a Charlottesville resident.
“I go over to Tony’s house,” O’Connor said, “and he goes, ‘Hey, I thought of you and your son. We’re going to go walk across the street and spend time with Muhammad Ali.’
Brian O’Connor, Muhammad Ali and Tony Bennett watch together a replay of one of Ali’s fights. The star UVA coaches met the boxing legend in October 2014. (Contributed photo)
“I was like, ‘What?’ I couldn’t believe it.”
An unforgettable experience transpired.
“It was an incredible night to spend time with Ali and his family,” O’Connor said, “but what I thought about after was, ‘Geez, how great of a guy is Tony Bennett to think of others, rather than it being about him?’
“And I think that’s a small story of many stories. Everybody has a story of how this man has impacted their lives.”
Ahead of Saturday’s celebration of Bennett at John Paul Jones Arena – tributes will take place throughout UVA’s 5:30 p.m. game against Georgia Tech and a banner will be raised at halftime – UVA Today collected more testimonies of Bennett’s legacy beyond the court.
A Prayer With Kayla
Away from the pregame buzz of a packed arena was the quiet of Bennett’s office. That’s where Jonathan Cotten and his daughter, Kayla, found themselves on Jan. 11, 2020.
Bennett was nine months removed from leading the Cavaliers to a national title and had them rolling again with a No. 18 ranking ahead of an ACC matchup with Syracuse University. But at that moment, some 30 minutes from tip-off against the Orange, basketball hardly mattered.
Bennett’s focus was Kayla, a young woman he met a few days earlier at his weekly radio show at the Boar’s Head Inn. She has gastroparesis, a paralysis of the stomach that’s triggered more than 100 visits to the emergency room during the course of her life. She’s also a sexual assault survivor, stemming from an incident at Lynchburg College in 2018 that eventually led to her withdrawal from the school.
The more Bennett learned about Kayla’s story, the more he wanted to help.
A UVA men’s basketball staffer escorted the Cottens from their seats to Bennett’s office, where Bennett and team chaplain George Morris greeted them.
“I can just picture Tony’s face,” Jonathan said, “and I can just hear the words that he said. ‘Kayla, when I met you there on Wednesday night, I went home and told my wife, Laurel, that I’ve met a sister in Christ.’”
The four then prayed together.
“It wasn’t the quantity of words, but it was just the authenticity of it, the thing that you knew that this wasn’t some calculated thing,” Jonathan said. “This was a reflexive action on part of his heart and showed who he is.”
This picture with Tony Bennett and my daughter, Kayla, was 5 years ago today. It changed my life and gave hope to Kayla at an extremely difficult moment. Here is a short summary:
* Kayla was diagnosed with gastroparesis (paralysis of the stomach) with the underlying cause of… pic.twitter.com/TxHsSPIspw— Jonathan Cotten (@JonEasystep) January 11, 2025
Mutual Respect
Among the fun elements associated with the Bennett era were the witty posts coming from “Phony Bennett,” the X account managed by UVA alumnus Chris Dembitz, pretending to be Bennett.
Under the handle @IfTonyTweeted, Dembitz, a former stand-up comedian, grew an audience of more than 24,000 followers. While that flock never included the actual Bennett, who refrained from social media, it did catch his attention.
The real Tony Bennett finally meets the man who played him on social media, Chris Dembitz. Four years after their introduction, when Dembitz passed away, Bennett sent a heartfelt video to Dembitz’s wife, Racheal. (Contributed photo)
“Bennett himself is on record as saying he thinks Phony Bennett is funny,” Whitelaw Reid wrote in a 2018 UVA Today profile of Dembitz. “He has said that he doesn’t mind what Dembitz is doing ‘as long as he keeps it respectful.’ And that is something Dembitz said he has always tried to do.”
When Dembitz, after an 18-month battle with cancer, died on May 2, 2023, Bennett not only expressed his condolences through a public statement, he sent a personalized video to Racheal Dembitz, Chris’ wife, who then passed it along to other members of Chris’ family.
“It was so heartfelt and meaningful,” Racheal said. “He just let us know how much he appreciated Chris’ contributions and how he always kept the account respectable.”
The clip has since been saved on numerous phones and laptops to ensure the family never loses it.
“Even for someone who doesn’t necessarily follow college basketball until Chris and I were together, I could see Coach Bennett’s character,” Racheal said. “Beyond the wins and all that, he just had this upstanding character that I know Chris respected so much.”
Sharing Happy Hugs
The gathering of UVA fans who waited in the rain for the team to return to JPJ from New York after a loss in the 2014 NCAA Tournament included Anna Schick, a young girl with Down syndrome who loves few things more than the Wahoos.
As Bennett and his players stepped off the bus, they met their supporters and thanked them for coming out.
And then Anna went in for a hug,
“And Tony hugged her back,” said UVA alumnus John Schick, Anna’s father, “and he said, ‘I love hugs. This is awesome. This is the best.’”
Genuine smiles cross the faces of Anna Schick and her friend, Tony Bennett. The UVA fan and coach share a special bond. (Contributed photos)
The hugs only continued from there. They embraced at Bennett’s radio shows or just by a courtside tunnel at JPJ after games.
“Down syndrome kids,” John said, “they don't have great stature, they’re kind of short, so they can kind of get bumped around in the hallways at school. So, when they get buoyed up by somebody who takes an interest in them and gives them hugs and says ‘thank you for being a fan’ and all that kind of stuff, it always makes her day.”
Anna, 22, who also has a close bond with Ty Jerome, said Bennett makes her “happy.”
“I love him,” she said.
The Best Wedding Gift
The video started and Doug Corbett turned to his new wife in shock. “Oh my gosh,” he whispered to Jenna. “Is he here?”
While Bennett couldn’t make it to Doug and Jenna’s wedding last October in Scottsville, he did offer a surprise toast at the reception.
Doug Corbett watches the wedding gift he received from his wife, Jenna, a personalized video and message from Bennett. (Contributed photos)
There, playing on a big screen for their 110 guests, was a two-minute speech on coaching, life and marriage.
A few months earlier, Jenna had written a letter to Bennett, explaining her fiancé’s career – tennis coach at Maryville College in Tennessee – and his admiration for Wahoo basketball – Doug’s a Charlottesville native and the son of a UVA alumnus.
All Jenna hoped for in return was a small note from Bennett she could frame as a wedding gift to Doug.
