Bill Simmons isn’t buying the Tom Brady coaching booth hysteria

Everyone’s losing their minds about Tom Brady sitting in the Raiders’ coaching booth with a headset on Monday night, but Bill Simmons isn’t having it.

While the sports media world exploded over Brady’s appearance in Las Vegas during the Raiders’ loss to the Chargers — complete with ESPN revealing that he talks with offensive coordinator Chip Kelly “two to three times a week” about game plans — The Ringer founder took the road less traveled. And it’s not because the Sports Guy will do anything he can to defend the honor of the Boston sports scene. He’s actually warned that it’s “dangerous” for the Raiders to give Brady so much personnel control, calling it problematic when great players think they can evaluate talent just because they were great themselves.

But on the coaching booth controversy, Simmons isn’t subscribing to the public outcry.

“I’ve done the basketball version where you get to meet the coach and talk about players,” Simmons said on his eponymous podcast. “It’s a little overrated. It’s not like they’re like, ‘Here’s our game plan.’ It’s more stuff like, ‘We really like Tucker Kraft. He’s been a pleasant surprise.’ It’s not, ‘Here’s our gameplan.'”

On the Tom Brady *controversy* (from Tuesday’s pod) pic.twitter.com/DDwq8R4rUK

— Bill Simmons (@BillSimmons) September 17, 2025

But Simmons had backup. ESPN’s Mina Kimes, who actually participates in these production meetings when she serves as a preseason analyst for the Los Angeles Rams, echoed his sentiment about the supposed competitive advantage everyone’s worried about.

“I am a little surprised at how upset some people are about the competitive integrity side of it,” Kimes said. “Obviously, preseason games are very different, but I was kind of asked last night, ‘So, have you ever really gotten something in a production where you were like, ” Whoa, I can’t believe they’re telling us this?’ And you’re right, it’s pretty mundane stuff. So, I don’t feel like he’s compromising, like he has an unfair advantage for his team.”

Kimes acknowledged that the optics might bother people — “the appearance of oh, he’s above the rules. Of course, Tom Brady gets to do it,” — but dismissed concerns about actual competitive harm.

“I don’t think the actual substance of it is that bad,” she added.

Simmons agreed, drawing from his own experience announcing a Lakers game during Mike D’Antoni’s coaching tenure. The insights weren’t strategic gold mines, just coaching staff getting “more comfortable” and offering casual observations about players.

“But then if they mention a player, ‘I’m really excited about this player. He’s made big strides.’ You’re like, OK, you file that away, and that’s how you hear, ‘When we talked to Mike before, he told us he really liked how so and so was playing,'” Simmons explained. “They might tell you one thing. Like, [Cris] Collinsworth will be like, ‘They told us they were going to try that before the game,’ some sort of double pass or something. Other than that, they’re not giving you game strategy.”

Regardless of whether you agree with Simmons’ take on the optics, the Brady controversy has officially reached its fever pitch. Monday night’s ESPN broadcast showed Brady not just observing but actively engaged with the Raiders staff. Peter Schrager reported that Kelly “uses him as a resource every single week,” and Dan Orlovsky revealed that defensive coordinator Patrick Graham received texts from Brady about tackling issues.

That visual of Brady slumping in his seat when the cameras found him — clearly uncomfortable being shown — became the smoking gun for critics who’ve spent months arguing about his dual roles, with everyone from current NFL players to media personalities piling on. Boomer Esiason called Brady’s situation with the Raiders and Fox “complete and utter B.S.” Marcus Spears said it “compromises the integrity” of the league.

And timing just makes everything worse.

Brady’s scheduled to call Bears-Cowboys this Sunday for Fox, and the Bears play the Raiders the following week. Ben Johnson’s Chicago squad now has to decide how much they’re willing to share with a broadcaster who’s literally wearing headsets in their upcoming opponent’s coaching booth.

The NFL tried to downplay the situation, issuing a statement Tuesday that “There are no policies that prohibit an owner from sitting in the coaches’ booth or wearing a headset during a game.” But that bureaucratic response missed the point entirely. This has never been about policy violations, it’s about the impossible situation the league created by allowing Brady to maintain both roles.

“I get why people don’t like it, I’m just not worked up about the competitive part of it,” Kimes concluded.

The real issue isn’t what Brady learns in production meetings. It’s what Monday night’s broadcast revealed about his actual involvement with Raiders operations. Chip Kelly consulting with him multiple times per week about game plans crosses every conceivable line, regardless of what the NFL’s policy manual says.

Whether Simmons and Kimes are right about production meetings being meaningless won’t matter if teams start shutting Brady out entirely. The Bears face that exact decision this week.