David Letterman Shared a Barrage of Sports Takes in Interview With Bill Simmons

1. If you’re like me and desperately miss seeing David Letterman on TV every day, his appearance on Bill Simmons’s podcast over the weekend was a true gift, especially since the legendary talk-show host does not do many interviews.
If you’re a Letterman fan, I can’t recommend the interview enough. Dave was relaxed (for him) and was very into the interview (also surprising for him).
Sports was a major part of the 75-minute conversation. Here are some of the notable highlights.
• Letterman told Simmons that he rarely watches TV anymore. Except for one show.
“Do you want to know the show that I do watch, and I get a little edgy if I miss it or if it’s preempted or something,” said Letterman. “It’s on ESPN and it’s Pardon The Interruption.”
Letterman explained, “I find something pleasant and welcoming, they’re both avuncular, Tony Kornheiser looks like my new dog so I have that connection.”
• Letterman revealed that after Michael Jordan did his show once, Dave was never able to get him back on the show.
After Simmons said, “I remember Michael Jordan, the first time he came on, he was great, you could tell he had it,” Letterman dropped a bomb.
“You could tell he had it, but he had a disliking for me,” said Letterman. “He was on once and he was on to promote his Air Jordans. … We couldn’t get him back. He would never come back. I finally called him because I kept imagining that I had offended the guy, and I certainly didn’t want that to have happened.
“And I called him and I flat-out asked him, I said, ‘We really would like you to come back. Is there a problem?’ He said, ‘No, not a problem.’ But he never came back. A real disappointment.”
• Letterman has an idea he’d like the NFL to implement for games that are tied after overtime.
“At the end of regulation, the score is 7-7. We have another full overtime period. If at the end of the overtime the score is still tied, what do we do? We have a kick out. We start the kicker at the 50, he makes it, then the other kicker on the opposing team has to duplicate that. If they both score, then go to the 55-yard line. And if that works, you go to the 60. And the first one that can’t convert a kick, the game is over. What’s wrong with that?”
While the idea may sound a little wacky, Letterman did a make a decent point to Simmons.
“If you can’t determine the outcome of the game in five quarters by moving the ball on the ground, passing and running, O.K., you’re paying the price for that. We’re turning into over to the kicker. It’s ‘FOOTBALL’ for the love of crap.”
Again, if you are fascinated by Letterman, this interview is a must-listen. The sports stuff was outstanding and the non-sports stuff was even better.
2. The latest SI Media With Jimmy Traina features segments with Richard Deitsch of Sports Business Journal and Mike Vaccaro of the New York Post.
The podcast kicks off with Deitsch discussing the latest sports media news. Topics include ratings for the NFL draft, NBA playoffs and Kentucky Derby, the status of Inside the NBA, CBS having interest in Russell Wilson, the future of Dianna Russini and much more.
Following Deitsch, Vaccaro joins the podcast to discuss the legendary career of John Sterling. The columnist details his relationship with Sterling while explaining what made Sterling unique and analyzing Sterling’s massive popularity among Yankees fans.
Following Vaccaro, Sal Licata, from SNY TV and The Sal Licata Show, joins me for our weekly “Traina Thoughts” segment. This week’s topics include my review of Netflix’s Hulk Hogan documentary, the Kentucky Derby, the Knicks’ playoff run, Ben Stiller choosing the Met Gala over the Sixers-Knicks playoff game and more.
You can listen to the SI Media With Jimmy Traina podcast below or on Apple and Spotify.
You can also watch SI Media With Jimmy Traina on YouTube.
3. We all know about the elbow that Victor Wembanyama threw at Naz Reid Sunday night. But what I want you to focus on and keep your eyes on is San Antonio’s Dylan Harper (No. 2) in the background. His face says it all.
Status alert: Victor Wembanyama has been ejected Sunday after being assessed a Flagrant 2 foul. pic.twitter.com/G02YylonQE
— Underdog NBA (@UnderdogNBA) May 11, 2026
And now the close up.
— Kellan Olson (@KellanOlson) May 11, 2026
4. Some NFL scheduling notes for the full schedule release on Thursday night:
Netflix will air five games this season. Two on Christmas Day, one on the night before Thanksgiving, one in Week 18 on Saturday and the Niners-Rams game from Australia on Thursday night in Week 1.
The season will open on a Wednesday night, Sept. 9, this year with the Seahawks hosting a yet-to-be-named opponent.
The Week 1 Sunday night game on NBC will be Giants at Cowboys.
5. If you’ve been on social media at all since the Knicks degraded the Sixers on Sunday afternoon, you’ve likely seen the video of the Philly reporter, Cheyenne Corin, trying to do her job outside the arena only to be bombarded by New York fans.
Give Corin a lot of credit. Based on her posts, she couldn’t have been a better sport about what happened.
😅 thank for sharing! This felt like a humiliation ritual in my own hometown 😩 but it’s Sixers for life 💙❤️ https://t.co/RH2Q72sPgC
— Cheyenne Corin ✨ (@CheyenneCorin) May 10, 2026
I was absolutely trolled on live TV by Knicks fans today 😅 But hey, it’s all in good fun. They better watch out for when it’s our turn though…. SIXERS FOR LIFE ❤️💙 pic.twitter.com/MYd3YKrrRj
— Cheyenne Corin ✨ (@CheyenneCorin) May 10, 2026
Just moments before while me & Jason were in the team coverage boxes everything was calm… until it wasn’t 😆 https://t.co/n57YhP1qjU
— Cheyenne Corin ✨ (@CheyenneCorin) May 11, 2026
6. I’ll give Draymond Green credit for one thing. This was a decent attempt at gaslighting after he tried to embarrass and insult Charles Barkley.
Draymond provides clarity Charles Barkley interaction
— The Draymond Green Show (@DraymondShow) May 9, 2026
“The reason that I would even say that is what Chuck makes fun about in his career is actually the last 2 years in Houston... everybody tried to make it like this whole 'Ahh man Draymond think he better than Chuck'... the… pic.twitter.com/lXrTY7Umk9
7. RANDOM VIDEO OF THE DAY: Whether you find this sketch from this weekend’s Saturday Night Live funny is obviously completely subjective. (I found it very funny.) But what can’t be disputed is that this was an amazing job of memorizing and delivering lines by Matt Damon and Sarah Sherman.
Be sure to catch up on past editions of Traina Thoughts and check out the Sports Illustrated Media Podcast hosted by Jimmy Traina on Apple, Spotify or Google. You can also follow Jimmy on X and Instagram.

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.