Podbit · The Bill Simmons Podcast
LeBron James' prolonged free agency deliberation is causing real problems for NBA scheduling, with commissioner Adam Silver flagging the issue publicly. Bill Simmons remains convinced Cleveland is the destination, despite prediction markets briefly spiking Miami to 55%.
Where this was said
At 1:31:34 · chapter starts 1:09:00
The debate is framed by Chris Ryan's opening observation: DiCaprio has twice as few films as Damon and treats himself like a brand — only Leonardo DiCaprio parts with Leonardo DiCaprio directors. Damon, by contrast, will pop up in a Soderbergh garage shoot, do SNL, and take ensemble supporting roles. Bill walks through a dozen custom categories. Damon wins: iconic rewatchables (Rounders, Bourne, Ocean's Eleven, Interstellar), action films (the entire Bourne franchise), ensemble movies (Ocean's, Oppenheimer, Saving Private Ryan), comedy, range, TV work, screenwriting, and director buddies in sheer number (Soderbergh, Nolan, Lonergan, Kevin Smith). DiCaprio wins Oscar bait, most iconic single movie moments (the Titanic prow, the bear scene), younger films, and Best Picture batting average [1] — Bill Simmons "Bill Simmons built a full category-by-category case for why Matt Damon deserves to be in the conversation with DiCaprio. Damon wins action …" 1:08:24 . The Departed head-to-head is a draw: DiCaprio won the movie but Damon had the harder part. Both agree The Odyssey — Damon playing Odysseus in Christopher Nolan's technically groundbreaking epic — is the best Damon has ever been, and Chris Ryan concedes that after seeing it, he would rather have Damon's career than DiCaprio's.
Matt Damon has approximately 100 acting credits compared to Leonardo DiCaprio's 48 (including TV), illustrating Damon's willingness to say yes to a wide variety of projects.
Matt Damon turned down Avatar to film Bourne Identity. The deal would have given him 10% of box office, which would have been worth approximately $250 million.
Leonardo DiCaprio has cited not doing Boogie Nights as his biggest career regret, though skipping it also meant he was available to make Titanic.
Matt Damon's films have grossed an estimated $12 billion at the box office, nearly double Leonardo DiCaprio's $6.5 billion, though Damon has made roughly twice as many movies.
Thomas's wife deferred her CrossFit career — she's in the global top 1% of athletes — to put him through law school debt-free. He wants her to chase the dream now; she wants the emergency fund and house down payment first. On a $200K lawyer income with no debt, the opportunity cost is just a few months of slower saving.
Underground calisthenics battles are exactly like UFC meets a rap battle — 150 people crowded around a circle, fighters walking out with masks and chains, nicknames like 'Extra Money' vs 'Calisthenics the Prince,' and people throwing money and betting. The battle set: 100 burpees, 50 muscle-ups, 75 dips, 75 squats with a 65-pound dumbbell. This is the next big spectator sport.
Rico Verhoeven controlled the undisputed heavyweight boxing champion for approximately 10 rounds — and had his appeal upheld when officials admitted the fight was stopped after the bell. The result was never overturned. Rogan calls it either incompetence or corruption, and argues the money behind Usyk made an upset politically inconvenient.
Rogan lays out a blunt case: boxing's 3-judge system is structurally broken, and the judges know who the promoter wants to win. Glory's 5-judge format is the right model. Corruption doesn't have to be conscious — just knowing Usyk is the cash cow is enough to tilt the scales.
With the Usyk-Wilder fight stalling and Fury-Joshua coming too late, the real fight the world wants is the rematch. Rico is a free agent. Usyk vacated his belts. The story is unfinished and both Rogan and Rico know it. His Excellency Turki Alasheikh already called for it ringside — the question is money.
Rico texted Jason Statham during the Canelo-Crawford fight. Statham showed Rico's highlight videos to promoters. Two days later, Rico was on a call about fighting Anthony Joshua. When Joshua pulled out, Rico pitched Usyk himself — Undisputed vs. Undisputed. Usyk said yes in two weeks. The whole thing started with one text.
Every heavyweight who faced Usyk tried to move to the right — straight into his power hand. Rico and Peter Fury identified the obvious solution: move left, away from the left hand, and smother him with size. It sounds simple. Nobody had done it. That one adjustment was the foundation of 10 dominant rounds.
MMA fans boo when fights go to the ground. They love stand-up. Kickboxing is pure stand-up. Yet it barely exists in America while boxing and MMA are enormous. Rogan's diagnosis: no promotion machine. If the UFC got behind kickboxing the way they've built MMA, it would explode. The talent is there — the storytelling machine is not.
A nation of 17 million people gave the world Ramon Deckers, Peter Aerts, Badr Hari, Melvin Manhoef, Rob Kamen, Ernesto Hoost, and Rico Verhoeven. Rico's theory: the country is so small that every gym shares knowledge freely. In the US, you need a flight. In Holland, you drive 40 minutes and spar the national champion.
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