The boss professed getting a lot of enjoyment from watching tennis, so Sam Winterbotham wasn't surprised to count him as a regular in the stands when Tennessee was on the court.
But when the Vols' coach began noticing that the guy who hired him was seemingly in the crowd for every other sport on campus as well, Winterbotham started realizing there might be something more at work than an affinity for rackets.
Mike Hamilton seemed to have an even greater appreciation for UT than any one particular sport, and his surprising resignation as athletic director on Tuesday morning only reaffirmed that to one of the most successful hires.
"It's a tough day," Winterbotham said when reached by phone during his vacation in Oklahoma. "He (Hamilton) deeply cared about the university. I'd take my kids to watch soccer, and Mike would always be there. He took his job very seriously, and he wanted everybody involved to feel important.
"He's a great boss and just an outstanding human being. It's terribly sad. He wanted Tennessee to be great, and he continues to want Tennessee to be great. He's just doing the best thing for Tennessee in his mind."
Mike Hamilton announces his resignation as Athletics Director for the University of Tennessee
That meant stepping aside after eight years of service at the top of the athletic department, a run that had some great moments but ended as UT closes in on a hearing with the NCAA Committee on Infractions.
Winterbotham's hiring and impressive resume with the Vols obviously doesn't come up early in a conversation about Hamilton's legacy thanks to the large shadows cast by football and men's basketball, though coaches from both those sports also stepped up to thank Hamilton for his work and the chance to come to UT in the first place.
"I will obviously be grateful for the opportunity Mike gave me to be the head football coach at Tennessee," Derek Dooley said in a statement. "The tremendous support he provided our staff and program has allowed us to set a strong foundation for the future of Tennessee football."
For all the fundraising, building renovations and construction that has gone on during Hamilton's reign, he will likely be judged by what happened with the highest-profile team on campus over the last few years - and the job Dooley does with it after he's gone.
Hamilton fired a coach in Phillip Fulmer with a national championship to his credit in 2008, brought in Lane Kiffin for a tumultuous season that produced part of the NCAA's case against UT this week and then had to hire a third guy in as many seasons after Kiffin bolted for Southern California and left a roster in disarray from the upheaval.
While that was going on, UT's other big moneymaker was enjoying unprecedented success with Bruce Pearl leading the basketball program - but that also was undone by violations off the court that prompted Hamilton to make another personnel change in March.
"I went to work every day trying to reward Mike Hamilton for giving me the opportunity of a lifetime," Pearl said in a statement to the News Sentinel. "I'm grateful for him bringing me to Tennessee. For the majority of time I was his men's basketball coach, we built something very special.
Reactions to news of Mike Hamilton's resignation
"I am so sorry that some of my mistakes and the results from them contributed to all that our athletics family and university have been through. The greatest fans in college athletics, supporting one of our nation's finest universities, deserve better. As Mike alluded to in his resignation, perhaps this will end some of the turmoil and the focus can shift back to all the positives the Vols have accomplished and will continue to accomplish."
The latter will happen without Hamilton watching over the Vols, a part of his now former job he literally did as much as possible.
He'll still be able to do that as the program moves on without him thanks to the lifetime season tickets he was given for football and basketball as part of his resignation package of $1.335 million. And Winterbotham might just save him a seat as well.
"In my time at UT, I've realized this is an incredibly passionate fan base with high expectations," Winterbotham said. "Mike had those same expectations and worked incredibly hard to meet them.
"Everybody in college athletics understands the business we're in, and this is a great university and it's going to continue to be."