Podbit · The Bill Simmons Podcast
Bill's dad admits he was ready to move on from Jaylen Brown after 10 years — but the trade package was horrendous. He ranks it alongside the Luka deal as one of the two worst trades he's seen in his lifetime. Street-level fan sentiment: nobody in Boston is defending it.
Where this was said
At 1:56:30 · chapter starts 1:19:01
Bill walks his dad through the full context: the Celtic-Philly playoff history they've witnessed together since 1977, the 3-1 series collapse last year, Embiid's three good games, the coaching shortcomings against Nick Nurse, and then the stunning summer — Jaylen Brown traded to Philly, LeBron follows, and now Boston's archival has a superteam. [1] — Bill's Dad "Bill's dad admits he was ready to move on from Jaylen Brown after 10 years — but the trade package was horrendous. He ranks it alongside th…" 1:56:30 Dad concedes he was ready to move on from Jaylen after 10 years of frustration — but the trade package was horrendous, and he'll never understand why Stevens accepted it. His street-level intel: not one Celtics fan he's spoken to on his dog walks around Boston is defending the trade, and the universal sentiment is they got 40 cents on the dollar. He places this alongside the Luka trade as the worst deals he's seen in his lifetime. [2] — Bill's Dad "Celtics ranked 4th of 4 Boston teams by Dad: Bill's dad ranked the Celtics last among Boston's four franchises in terms of optimism, behind…" 2:00:08 The question of why Tatum sat out Game 7 against Philly — never explained, never reported — adds another layer of frustration. Dad's final rankings of Boston franchise optimism: Patriots 1, Red Sox 2, Bruins 3, Celtics 4. The only hopeful note is that Brad Stevens has been excellent overall, so perhaps he sees something they don't — but neither Simmons believes it.
The Red Sox went on a 15-game winning streak that transformed their season after starting terribly, coinciding roughly with the Celtics' Jaylen Brown trade.
With Roman Anthony out for the year, Crochet hurt, and Trevor Story somehow improving the team by leaving, the Red Sox found their engine in Contreras — a lunatic who cares about every game. The 100-to-1 shot became the team's identity.
The 2026 World Cup in Boston was a massive success — Scottish fans in kilts took over Beacon Street outside Cheers, Norwegians did their rowing celebration on the Green Line, and the city fell in love with the tournament in a way nobody expected.
Red Sox top prospect Roman Anthony received a $100 million commitment but missed the entire season with a mysterious finger injury, leaving the team without its projected franchise cornerstone.
Brad Stevens traded Jaylen Brown to Philadelphia for Paul George and two first-round picks, a deal widely derided by Boston fans as receiving 40 cents on the dollar.
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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