Bill Simmons on Sports Media, His Time at ESPN, Podcasting, Gambling and Much More

1. The Ringer’s Bill Simmons made his first appearance on SI Media With Jimmy Traina this week.

The sports media powerhouse gave us insight into his successful career while also opining on some sports media topics during the 90-minute conversation. 

Some of the highlights included Simmons’s response when I asked him how he remembers his time at ESPN.

Bill Simmons Is ‘Super Proud’ of Time at ESPN (1:28)

Here’s why Simmons isn’t convinced Tom Brady will join Fox next season as its lead NFL analyst.

Bill Simmons Believes Tom Brady Is Unlikely to Become an Analyst (TV-PG; 2:04)

And Simmons gave us some details on the upcoming Netflix documentary he produced on Vince McMahon.

Bill Simmons Think Vince McMahon Documentary Is Awesome (TV-PG; 1:21)

A ton of ground was covered during the podcast. Here is a chronological rundown of the topics.

• Mixing sports with pop culture in his early writing days

• Vegas trips

• Over/under on how many sports writers will get in trouble at Vegas Super Bowl

• Why he doesn’t do many interviews on his podcast anymore

• Why he doesn’t use notes when doing interviews

• His prep for an interview

• Why he’s super proud of his time at ESPN

• Does he regret calling Roger Goodell a liar?

• What he’d do differently about that Goodell podcast

• His thoughts on ESPN’s transformation

• The problem with NFL studio shows

• Being terrified to do PTI in the early days

• The mistake that TV execs make

• Why he doesn’t think Tom Brady will go to Fox

• What’s happened with Tony Romo

• Joe Buck and Troy Aikman

• How longevity affects our relationship with announcers

• MLB and NBA have broadcasting problems

• MLB alternate broadcast idea

• David Stern squashing the Van Gundy brothers on same show

• His experience on ESPN’s NBA Countdown

• How he’d fix NBA Countdown

• The gambling explosion in sports

• How executive’s kids have a ton of power

• Current state of sports media being as murky as ever

• The Athletic’s turn

• Reminiscing about Dr. Z

• His upcoming Vince McMahon documentary

• Love for Mallory Rubin

• Mike and the Mad Dog

• Francesa asking Simmons to replace Russo

You can listen to the podcast below or download it on Apple, Spotify and Google.

You can also watch SI Media With Jimmy Traina on YouTube.

2. Former NFL players Jared Allen, Marcellus Wiley and Rashad Jennings were on the Wheel of Fortune on Wednesday night. It turned out to be a disastrous appearance for Jennings.

Football players are terrible at Wheel of Fortune pic.twitter.com/4e4UH3CQvm

— Brother Bri (@thebrotherbri) October 19, 2023

3. Eagles teammates D’Andre Swfit and Terrell Edmunds took in Game 2 of the Diamondbacks-Phillies series in Philadelphia on Tuesday night. Audio of some of their conversation about the sport of baseball was picked up, and it was pretty great.

View the original article to see embedded media.

4. Dolphins coach Mike McDaniel was asked whether any quarterback could do what Tua Tagovailoa is doing this season because of Miami’s system on offense. Thanks to McDaniel’s unique personality, he gave an aggressive answer that couldn’t have come off in a nicer way.

Mike McDaniel took significant exception when asked if he thought any QB could succeed in this situation:

“I’m about to push this podium over. My answer to that would be who the F cares? I’ve coached a long time and I haven’t seen people do what our guys do.” pic.twitter.com/25R63PYeKN

— King of Phinland🐬👑 (@KingOfPhinland) October 18, 2023

5. Chris “Mad Dog” Russo appeared on the Dan Le Batard Show With Stugotz on Wednesday and was in rare form as he shared his thoughts on Halloween and talked about the time he took too many gummies.

“Halloween, that’s another complete waste of time…nobody comes to my house…if they come, I give them all tootsie rolls because that ruins teeth.”

- @MadDogUnleashed is not a fan of Halloween…nor his mother-in-law’s cooking.

📺 https://t.co/OaGbtO43S4
🎙️… pic.twitter.com/uJNRY0xhqz

— Dan Le Batard Show with Stugotz (@LeBatardShow) October 17, 2023

“It hit me when I was about to eat a sandwich…I was about to open up the cabin and fly away.”

- @MadDogUnleashed details the time when he bit off more gummies than he could chew. 🛫☁️🛸☮️😂

📺 https://t.co/LdAVUe5gES pic.twitter.com/I37Qw4XJGt

— Dan Le Batard Show with Stugotz (@LeBatardShow) October 17, 2023

6. Aces owner Mark Davis celebrated his team's WNBA title Wednesday night by combining the dance moves that you'd totally expect from Mark Davis.

OKAYYY MARKKKKKK 🕺#WNBAFinals | @YouTubeTV pic.twitter.com/yK5m9KXArD

— WNBA (@WNBA) October 19, 2023