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

Also in Traina Thoughts: Former NFL RB has ‘Wheel of Fortune’ disaster; mic’d up NFL players at MLB playoff game is gold; Mike McDaniel is one of a kind; and more.

Jimmy Traina

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.

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

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

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.

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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.

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.

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.

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.

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.

7. RANDOM VIDEO OF THE DAY: RIP to actor Burt Young, who died Wednesday at 83. His role in the Rocky movies was vital, and he was fantastic.

Be sure to catch up on past editions of Traina Thoughts and check out SI Media With Jimmy Traina on Apple, Spotify or Google. You can also follow Jimmy on Twitter, Instagram and TikTok.

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Jimmy Traina
JIMMY TRAINA

Jimmy Traina is a staff writer and podcast host for Sports Illustrated. A 20-year veteran in the industry, he’s been covering the sports media landscape for seven years and writes a daily column, Traina Thoughts. Traina has hosted the Sports Illustrated Media Podcast since 2018, a show known for interviews with some of the most important and powerful people in sports media. He also was the creator and writer of SI’s Hot Clicks feature from 2007 to '13.

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