Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!)
Episode of The Bill Simmons Podcast · May 8, 2026 · 1 h 57 min
Bill Simmons shares NBA second-round playoff takes, then interviews David Letterman about retirement, late-night TV, yacht rock, comedy peers, sports rule ideas and Netflix.
Summary
In the first segment, Bill Simmons offered solo observations on the second round of the 2026 NBA playoffs. He argued that the Oklahoma City Thunder's depth made them too strong for a Luka Dončić-less Los Angeles Lakers team and predicted a sweep. He called the James Harden trade a disaster for Cleveland so far and questioned whether Evan Mobley had plateaued. He also predicted Detroit and New York would advance. He criticized the NBA's slow replay review and revisited the Boston Celtics' first-round collapse. Listener mail covered athletes who won him over, lottery karma and Giannis Antetokounmpo trade scenarios, including Dallas. He also discussed Boston's sports-radio turmoil and the Mike Vrabel–Dianna Russini story.
In the second segment, David Letterman made his first appearance on the podcast. He said the difficulty of retiring did not hit him for about two years and encouraged productive people to keep working. He recalled Johnny Carson's abrupt disappearance after retirement and his own 1970s years in Los Angeles at the Comedy Store and as a sitcom writer. He said a SiriusXM host had soured him on yacht rock until he saw Simmons's documentary. He named Pardon the Interruption as nearly the only TV he still watches.
The two discussed the uncertain future of late-night television and fame in the internet era. Letterman described the year after his NBC morning show was canceled as a dark period of heavy drinking. He pitched a kicking shootout for tied NFL games and other playful rule changes. He also recounted Michael Jordan declining to return to his show and told stories about Jay Leno, George Miller, Norm Macdonald and The Late Shift. Other subjects included a confrontation with Les Moonves and his view that the NFL's stake in ESPN seemed dubious. He praised Netflix as an employer and mentioned plans to attend a Caitlin Clark game in Indianapolis.
Chapters
Linked moment · 0:06Skip to 0:06 using a listen link in the info box.
0:06Intro and Letterman bucket list
Simmons previews the episode and explains that Letterman was his top dream guest and the inspiration for his mailbag.
- 2:34
Thunder dominate the Lakers
Simmons breaks down OKC's Game 2 win, praises Ajay Mitchell's trade value and criticizes slow NBA replay reviews.
- 10:52
Cavaliers crumble against Detroit
Simmons says Cade Cunningham is the series' best player, calls the Harden trade a disaster and questions Evan Mobley's ceiling.
- 18:12
Knicks-Sixers and the Celtics post-mortem
Simmons expects the Knicks to win quickly and revisits Boston's first-round loss to Philadelphia.
- 21:59
Mailbag: Rocky IV athletes, Spurs-Wolves, lottery and Giannis
Simmons names athletes who won him over, assesses Spurs-Wolves, adjusts lottery karma rankings and weighs a Giannis-to-Dallas scenario.
- 30:24
Boston sports radio chaos and the Vrabel story
Simmons compares Boston's current sports turmoil to 1996-97 and reacts to new Vrabel–Russini revelations.
- 38:53
Letterman on fatherhood and retirement
Letterman discusses his son, his final show and how the difficulty of retiring set in only years later.
- 44:19
Carson, yacht rock and 1970s California
Letterman recalls Carson's post-retirement disappearance, his change of heart on yacht rock, the Comedy Store years and his early writing jobs.
- 1:00:51
TV today, PTI and the future of late night
The pair discuss fragmented media, Letterman's love of Pardon the Interruption, late-night hosts and fame in the internet age.
- 1:16:08
Sports rule-change ideas
Letterman pitches an NFL kicking shootout, quarterbacks who punt and other rule tweaks, and the two discuss golf, F1 and the Masters.
- 1:28:03
Memorable guests, Leno and The Late Shift
Letterman talks about Michael Jordan, Jay Leno, George Miller, Norm Macdonald and Andy Kaufman, and his dislike of The Late Shift.
- 1:37:48
Netflix, bosses, Indianapolis and Caitlin Clark
Letterman praises Netflix and recalls clashing with Les Moonves, and they discuss the NFL's ESPN stake, Indiana basketball and Caitlin Clark.
Key points
What was said, by whom, with the exact words. Timestamps jump to the moment.
- Bill SimmonsCame true
Simmons predicts the Lakers will be swept by Oklahoma City unless the Thunder have a very poor shooting game.
“And they're going to get swept unless, okay. See just has a game where they shoot like 30%, which I don't see it happening”
- Bill Simmons
Simmons argues the NBA should speed up replay reviews and improve its product before expanding.
“So maybe instead of expansion, maybe try to improve the product before we start adding teams to the product would be my advice”
- Bill Simmons
Simmons calls Cleveland's James Harden trade a disaster so far, unless it is viewed as a salary dump.
“So this trade so far has been, um, a disaster unless you just think of it as a salary dump and maybe that's what it was”
- Bill Simmons
Simmons worries that Evan Mobley has plateaued as a player.
“The fear is he might be a, you are where you are guy at this point”
- Bill SimmonsDidn’t happen
Simmons predicts Detroit will beat Cleveland because the Pistons are more physical and have the best player.
“I think they have the best player, and I think they're going to win this series”
- Bill Simmons
Simmons argues the Celtics never believed they could lose to Philadelphia and treated the series as an experiment.
“i don't think they ever thought they were losing to philadelphia i think they used the series as this testing ground”
- Bill SimmonsCame true
Simmons predicts the Knicks will beat the 76ers in five games or fewer.
“I would just be surprised if this went more than five games”
- Bill Simmons
Simmons reads Brad Stevens's end-of-season comments as hints toward a Giannis trade.
“it felt like he was laying a lot of breadcrumbs to Giannis' trade”
- David Letterman
Letterman says the difficulty of ending his show did not sink in until years after he retired.
“So the real difficulty of it didn't set in for about, I don't know, a year or two, three years”
- David Letterman
Letterman advises people who are productive and happy to keep working rather than retire at a set age.
“So if you're productive and happy, just keep going for God's sakes”
- David Letterman
Letterman says a SiriusXM yacht rock host soured him on the genre until Simmons's documentary restored his respect for it.
“I hate that guy and is what poisoned Yacht Rock for me until I saw your documentary”
- David Letterman
Letterman finds it discouraging when a guest host fills in for one of Pardon the Interruption's two regular hosts.
“Whenever there's a guest host or somebody filling in for one of the two, it's discouraging”
- David Letterman
Letterman says he rarely used guest hosts because he feared losing his show if he gave up the chair.
“deadly scared that if I gave up the seat, I'd lose the show”
- David Letterman
Letterman recalls spending his year out of work after the NBC morning show drinking heavily.
“mostly I was drinking and drinking to excess. And it was, it was a dark year”
- David Letterman
Letterman proposes settling tied NFL games with an escalating field-goal kick-off between the two kickers.
“We start the kicker at the 50. He makes it. Then the other kicker opposing team has to duplicate that”
- Bill Simmons
Simmons calls baseball's pitch clock the most successful new rule idea in sports.
“Baseball's pitch clock is the single most successful new idea I think anyone's come up with”
- David Letterman
Letterman says he is pleased that LIV Golf appears to be having financial troubles.
“I'm so pleased that the Live Golf Tournament seems to be having financial troubles”
- David Letterman
Letterman recounts personally calling Michael Jordan to ask him back on the show, but Jordan never returned.
“I called him and I flat out asked him, I said, we really would like you to come back”
- David Letterman
Letterman says Jay Leno was the funniest comic in their Comedy Store group.
“When we were working at the comedy store, he was the funniest in the group”
- David Letterman
Letterman praises Netflix as an employer, unlike his past bosses.
“They've been nice. They've been friendly. They're pleasant”
- Bill Simmons
Simmons says ESPN suspended him for criticizing Roger Goodell and concedes he probably went too far.
“I was very critical of Roger Goodell and knowing that he was their biggest partner and, you know, in retrospect, probably pushed a little too far”
- David Letterman
Letterman questions whether it is appropriate for the NFL to own a stake in ESPN.
“So is that okay? That the single biggest topic of the sports broadcasting owns that outlet? It seems a little dubious”
- Bill SimmonsPrediction · due Apr 2027
Simmons predicts the Indiana Pacers will be very good next season with Tyrese Haliburton returning and a new center.
“They traded for a center. So I think they're going to be really good next year”
People
In the conversation
- Bill SimmonsSportswriter and founder of The Ringer, host of The Bill Simmons Podcast
- David LettermanLate-night host who competed for The Tonight Show
Discussed
- Johnny CarsonLongtime Tonight Show host whose chair was the goal of a generation of comics
- Jay LenoComedian, former Tonight Show host and car collector
- George MillerStand-up comedian and friend of Letterman
- Norm MacdonaldCanadian comedian and frequent Letterman guest
- Michael JordanBasketball player used by Hudson in an example about condescending encouragement
- Caitlin ClarkWNBA player
- Les MoonvesFormer CBS chief executive
- Roger GoodellNFL commissioner
- John MulaneyAmerican comedian and frequent Kroll collaborator
- Michael McDonaldSinger who wrote the theme for Letterman's NBC morning show
- Jimmy MurphyAmerican racing driver who won the French Grand Prix in a Duesenberg
- James HardenGuard traded to Cleveland during the season
- Evan MobleyCleveland Cavaliers forward
- LeBron JamesLos Angeles Lakers forward cited as a longevity outlier
- Ajay MitchellOklahoma City Thunder guard
- Brad StevensBoston Celtics president of basketball operations
- Tony KornheiserCo-host of Pardon the Interruption
- Jimmy KimmelABC late-night host targeted by the White House
Topics
- 2026 NBA playoffs
- Late-night television hosting
- Oklahoma City Thunder
- Cleveland Cavaliers
- Boston Celtics
- Giannis Antetokounmpo trade speculation
- Yacht rock
- Pardon the Interruption
- Retirement
- Mike Vrabel–Dianna Russini boat photos
- The Late Shift
- Automated ball-strike system
- LIV Golf
- The Comedy Store
- NFL overtime rules
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From the publisher
The Ringer’s Bill Simmons give his thoughts on various topics around the NBA with Round 2 of the playoffs well underway (3:06). Then, David Letterman comes on to talk about his upbringing, the evolution of talk shows, sports, and much, much more! (38:51). Host: Bill Simmons Guest: David Letterman Producers: Chia Hao Tat and Eduardo Ocampo This episode is sponsored by State Farm®. Like a good neighbor, State Farm is there.® The Ringer is committed to responsible gaming. Please visit https://fanduel.com/playwithaplan to learn more about the resources and helplines Learn more about your ad choices. Visit podcastchoices.com/adchoices
Summary, chapters and key points were generated from the episode transcript on September 28, 2026. Quotes are checked word for word against the transcript.