If you were paying attention toward the end of The Bill Simmons Podcast on Dec. 1, you might have been surprised to hear the Sports Guy take a side in a relatively obscure coaching search from all the way back in 2023.
During a conversation about Lane Kiffin as the mercurial coach arrived at LSU, The Ringer’s Van Lathan speculated that Kiffin overlooked Florida because of its athletic director’s reputation. Simmons then took a surprise shot at the Syracuse athletic department and the way it handled the head coaching search that ultimately led to Fran Brown taking over the Orange.
“(Florida AD Scott Stricklin is) worse than the Syracuse AD who didn’t hire Bob Chesney?” Simmons quipped.
“There’s some layers to it,” responded Todd McShay, who was also a guest on the episode.
On Wednesday, we found out what those layers were.
The main joke Simmons was making likely went over fans’ heads. The AD at Syracuse is John Wildhack, a longtime former ESPN executive who ran programming when Simmons and McShay both worked for the Worldwide Leader.
“He couldn’t do that job, either,” Simmons laughed.
But the layers go deeper than that.
Simmons was also not-so-quietly advocating for Chesney. Why? Because for five years, Chesney oversaw perhaps the most successful run for Holy Cross football of Simmons’ life. And Simmons is a Holy Cross graduate who clearly keeps a close eye on the football program at his alma mater.
The lobbying also went deeper than Simmons’ podcast quip. Chesney, who went to James Madison after being turned down by Wildhack and Syracuse, was just hired to take over in Simmons’ backyard at UCLA. And in an interview on Wednesday with the school’s in-house Bruin Insider Show, Chesney revealed that Simmons was one of his first and most prominent advocates as he pursued the UCLA job.
“I got a call pretty quickly, and there were some players involved in this that I knew from my past. One Bill Simmons, that’s I think pretty close with Casey Wasserman and another guy named Brett Veach who’s really close with Adam Peters,” Chesney explained. “And those were calls that happened way early, before anyone was even talking about this actually being a thing.”
For years, Simmons has shared a public friendship with Wasserman, a powerful L.A. impresario and sports super exec (as well as one of the more boring recurring podcast guests in the history of Simmons’ show). Wasserman, notably, served on the search committee for UCLA football this fall.
The Bruins fired DeShaun Foster in mid-September, before James Madison won the Sun Belt and made the College Football Playoff. If Simmons was, in fact, one of the first people to call Wasserman about Chesney, it likely happened far before he mentioned it on his podcast in early December.
Chesney is certainly a qualified coach, having developed potent mid-major teams at Holy Cross and JMU. But given that Simmons is notoriously uninterested in college football, the Sports Guy’s involvement in Chesney’s candidacy at UCLA is one of the more fascinating power plays in the sport this year.