An anonymous executive told Zach Lowe that only 3-4 NBA front offices have enough credibility to make the Jaylen Brown trade without suffering "immediate cataclysmic blowback" — and Boston barely qualified.
The Bill Simmons Podcast
An anonymous executive told Zach Lowe that only 3-4 NBA front offices have enough credibility to make the Jaylen Brown trade without suffering "immediate cataclysmic blowback" — and Boston barely qualified.
TL;DR
Bill Simmons and Zach Lowe kick off with England's dramatic 3-2 win over Mexico at Azteca in the World Cup Round of 16, debating VAR, reseeding, and Haaland's dominance [1] — Bill Simmons "England defeated Mexico 3-2 at Azteca in the World Cup Round of 16, going up 2-0 before Mexico clawed back to tie via penalty kicks — all w…" 01:15 . They pivot to the Jaylen Brown trade fallout — the league consensus is Boston got surprisingly little back, with the contract ($57–66M) and chemistry concerns driving the deal more than basketball ability [2] — Zach Lowe "Four days after the Jaylen Brown trade, the consensus across the NBA is unanimous: nobody thinks it was good for Boston. The return was sur…" 20:30 . A wide-ranging mailbag covers Christmas game predictions, LeBron's free agency, and the Mount Rushmore of "oh no" NBA trades. Key takeaway: salary cap anxiety, not analytics, is increasingly shaping franchise decisions [3] — Zach Lowe "Jaylen Brown's salary: $57M-$66M: Zach Lowe argued the main driver of the Jaylen Brown trade was his escalating salary — $57M, $62M, $66M —…" 29:29 .
Bill Simmons and Zach Lowe react to England's 3-2 World Cup victory over Mexico at Azteca, then dig into the Jaylen Brown trade fallout and take mailbag questions on Christmas games, LeBron's free agency, and the Mount Rushmore of bad NBA trades.
The episode opens with back-to-back sponsor reads: first a PNC Bank brand ad celebrating 'brilliantly boring' financial fundamentals, then a PayPal pitch touting the app's rewards stacking capabilities. Bill Simmons rolls in at the 75-second mark, establishing the recording context — it's late on the West Coast, Zach Lowe has agreed to stay up, and a planned live Netflix broadcast fell apart due to technical issues. Simmons teases a new Rewatchables episode covering the 1979 film Ali, and drops the first reference to what will dominate the pod's basketball section: the Jaylen Brown trade, which he frames as the closing chapter of what he called 'hell month.'
The hosts immediately dive into the England-Mexico match, with both agreeing there is simply nothing in sport that matches the weight of a World Cup knockout game. Zach Lowe articulates why: the every-four-years format makes every missed opportunity feel like a lost lifetime. Bill Simmons sets the scene at Azteca — an arena he visited in 2009 for a USA-Mexico qualifier — recalling how close the stands are to the pitch, the projectiles thrown at corner kicks, and the nerve-racking business of getting out safely after Mexico loses. England went up 2-0, Mexico clawed back via penalty kicks, England played a man down for the final stretch, and Jordan Pickford made several crucial saves to preserve the win. Simmons likens Jude Bellingham's role to Jaylen Brown playing second fiddle to Jayson Tatum — a joke that immediately gets called 'too soon.' Lowe also mourns Croatia's VAR-disallowed last-second equalizer against Portugal, declares he's throwing his allegiance to Norway, and goes full nuclear on replay technology across all sports: he wants VAR thrown into the ocean and NBA ref huddles abolished entirely. The pair debate whether offside rules should require millimeter precision or just a distinct lead, and Lowe drops his two main World Cup reform takes — no automatic tier-1 status for host nations, and reseed the bracket after the group stage.
Bill Simmons opens the basketball segment noting he's been getting texts, calls, and emails from people across the league since the trade. Zach Lowe delivers the verdict: no one can be found who thinks it was good for Boston, and the working consensus is that the bridge burned between Jaylen Brown and the organization beyond recovery — perhaps for reasons 'we may not fully understand but may one day fully understand.' Bill Simmons, fresh from a shower in which he genuinely tried to argue Paul George was undervalued, reads five Clipper-era stats in succession — 23-6-5, 39% from three, 8 All-Stars, 3.43 threes per game. Lowe's response is devastating: 'That was one of the sadder one-minute segments in the history of the Bill Simmons Podcast.' He clarifies that the Celtics are not secretly coveting Paul George — they know exactly who he is, a third/fourth option who fits Mazzulla's system. Lowe adds that a high-level rival front office executive told him that only 3-4 organizations in the league could execute this trade without 'immediate cataclysmic blowback' — and Boston barely qualifies. Both hosts also note the unusual dynamic of a new ownership group (Bill Chisholm's consortium) making a cost-cutting trade rather than the typical splashy new-owner buy-in.
A listener question asking whether the Jaylen Brown trade belongs on the Mount Rushmore of malpractice deals opens Simmons' best list segment of the episode. The definitive 'oh no' trades: the Luka Doncic trade (the clear number one, 'different species of horrible'), Barkley to Phoenix for Hornacek, Lang, and Tim Perry ('immediately calling Joe House'), Harden to Houston, Philadelphia trading the 1986 number 1 pick for Roy Hinson and $750,000, Portland dealing Moses Malone for $232,000 and one pick only for Buffalo to flip him for two number 1s six days later, and the Utah Jazz trading the 1982 number 3 pick (Dominique Wilkins) for John Drew and $750,000. Zach Lowe correctly notes the Jaylen Brown trade isn't comparable to the Luka deal in magnitude. Conspiracy Bill gets multiple entries: the Kawhi-to-Toronto theory (Adam Silver secretly orchestrating the trade to punish the Clippers' Aspiration scheme involvement), and the idea that Ballmer buying the Seahawks and selling the Clippers would provide cover for a quiet punishment. Listeners also get the Taylor Swift-Travis Kelce wedding fake-out, the Brad Stevens Godfather Part III analogy, and a very credible theory about Celtics clearing space for Cooper Flagg in 2028.
Chapter 2 · 01:15
The hosts immediately dive into the England-Mexico match, with both agreeing there is simply nothing in sport that matches the weight of a World Cup knockout game. Zach Lowe articulates why: the every-four-years format makes every missed opportunity feel like a lost lifetime. Bill Simmons sets the scene at Azteca — an arena he visited in 2009 for a USA-Mexico qualifier — recalling how close the stands are to the pitch, the projectiles thrown at corner kicks, and the nerve-racking business of getting out safely after Mexico loses. England went up 2-0, Mexico clawed back via penalty kicks, England played a man down for the final stretch, and Jordan Pickford made several crucial saves to preserve the win. Simmons likens Jude Bellingham's role to Jaylen Brown playing second fiddle to Jayson Tatum — a joke that immediately gets called 'too soon.' Lowe also mourns Croatia's VAR-disallowed last-second equalizer against Portugal, declares he's throwing his allegiance to Norway, and goes full nuclear on replay technology across all sports: he wants VAR thrown into the ocean and NBA ref huddles abolished entirely. The pair debate whether offside rules should require millimeter precision or just a distinct lead, and Lowe drops his two main World Cup reform takes — no automatic tier-1 status for host nations, and reseed the bracket after the group stage.
England defeated Mexico 3-2 at Azteca in the World Cup Round of 16, going up 2-0 before Mexico clawed back to tie via penalty kicks — all with England playing a man down. Azteca's atmosphere is unlike anything in sports: fans throw things at corner kicks, try to find the opposing team's hotel, and shoot fireworks at their buses.
England defeated Mexico 3-2 in the World Cup Round of 16, playing a man down for a significant stretch in a wildly dramatic match at Estadio Azteca.
Mexico had not lost a real international game at Azteca in approximately 13 years before England's Round of 16 victory.
After Croatia had a goal disallowed by VAR in the final seconds of their World Cup exit, Zach Lowe declared war on replay technology across all sports. He doesn't want to watch NBA refs huddle anymore, he doesn't want soccer's VAR hair-follicle offside checks — he wants results to stand on the field, full stop.
US striker Balogun shot 49% from three and averaged 16 points per game in the World Cup playoffs before his red card, which was later intervened upon and overturned.
Chapter 3 · 19:43
Bill Simmons opens the basketball segment noting he's been getting texts, calls, and emails from people across the league since the trade. Zach Lowe delivers the verdict: no one can be found who thinks it was good for Boston, and the working consensus is that the bridge burned between Jaylen Brown and the organization beyond recovery — perhaps for reasons 'we may not fully understand but may one day fully understand.' Bill Simmons, fresh from a shower in which he genuinely tried to argue Paul George was undervalued, reads five Clipper-era stats in succession — 23-6-5, 39% from three, 8 All-Stars, 3.43 threes per game. Lowe's response is devastating: 'That was one of the sadder one-minute segments in the history of the Bill Simmons Podcast.' He clarifies that the Celtics are not secretly coveting Paul George — they know exactly who he is, a third/fourth option who fits Mazzulla's system. Lowe adds that a high-level rival front office executive told him that only 3-4 organizations in the league could execute this trade without 'immediate cataclysmic blowback' — and Boston barely qualifies. Both hosts also note the unusual dynamic of a new ownership group (Bill Chisholm's consortium) making a cost-cutting trade rather than the typical splashy new-owner buy-in.
As the official beer sponsor of FIFA World Cup 26, Michelob Ultra is giving away $1 million in tickets and prizes through its Superior Access promotion.
Four days after the Jaylen Brown trade, the consensus across the NBA is unanimous: nobody thinks it was good for Boston. The return was surprisingly low even accounting for known skepticism about Brown's value, and the only explanation that makes sense is the bridge was burned past the point of no return.
Despite finishing 6th in MVP voting and earning All-NBA honors, Jaylen Brown's trade value was depressed primarily by his massive salary and analytical skepticism within the league.
Bill Simmons spent his morning shower compiling Paul George's actual career stats — five Clipper seasons at 23-6-5, eight All-Stars, an MVP third-place finish in 2019 — trying to convince himself Boston secretly covets George. Zach Lowe's verdict: 'That was one of the sadder one-minute segments in the history of the Bill Simmons Podcast.'
Over his 5 seasons with the Clippers, Paul George averaged 23 points, 6 rebounds, and 5 assists on 39% from three with 3.43 three-pointers made per game.
After returning from a 25-game drug suspension, Paul George averaged 21 points per game on 42% from three in his last 10 games of the season.
A high-level executive from another team told Zach Lowe that only 3-4 NBA front offices have enough credibility to make the Jaylen Brown trade without facing immediate, catastrophic fan backlash.
Zach Lowe argued the main driver of the Jaylen Brown trade was his escalating salary — $57M, $62M, $66M — which made him nearly impossible to build around alongside Tatum's even larger deal.
The Jaylen Brown trade may be the opening salvo of a new NBA era where teams treat the second apron like a hard cap. Zach Lowe reports that agents are already venting about this, and James Dolan let Mitchell Robinson walk rather than take the luxury tax hit — a championship team willingly getting worse to save money.
Zach Lowe recalled a period where the NBA salary cap stayed flat at roughly $58 million for three or four consecutive years, a similar dynamic to current second-apron pressures.
Chapter 4 · 34:04
A listener question asking whether the Jaylen Brown trade belongs on the Mount Rushmore of malpractice deals opens Simmons' best list segment of the episode. The definitive 'oh no' trades: the Luka Doncic trade (the clear number one, 'different species of horrible'), Barkley to Phoenix for Hornacek, Lang, and Tim Perry ('immediately calling Joe House'), Harden to Houston, Philadelphia trading the 1986 number 1 pick for Roy Hinson and $750,000, Portland dealing Moses Malone for $232,000 and one pick only for Buffalo to flip him for two number 1s six days later, and the Utah Jazz trading the 1982 number 3 pick (Dominique Wilkins) for John Drew and $750,000. Zach Lowe correctly notes the Jaylen Brown trade isn't comparable to the Luka deal in magnitude. Conspiracy Bill gets multiple entries: the Kawhi-to-Toronto theory (Adam Silver secretly orchestrating the trade to punish the Clippers' Aspiration scheme involvement), and the idea that Ballmer buying the Seahawks and selling the Clippers would provide cover for a quiet punishment. Listeners also get the Taylor Swift-Travis Kelce wedding fake-out, the Brad Stevens Godfather Part III analogy, and a very credible theory about Celtics clearing space for Cooper Flagg in 2028.
Bill Simmons revealed he was coming out of anesthesia when his wife broke the Jaylen Brown trade news to him. He literally could not process it. Zach Lowe adds that multiple NBA executives called him that day asking 'Is Bill okay?' — and their reactions upon finding out where Simmons was were described as the most gleeful laughing he'd ever heard from grizzled veteran league men.
The Celtics went on a run to win 56 games in the 2024-25 regular season despite a shaky start, which makes the decision to trade Jaylen Brown even more debated.
Simmons puts Jaylen Brown's blame pie at 45% salary, 40% self-awareness and role questions, and the rest on analytics. Lowe goes higher on contract — at least 50%. The on-off metrics don't tell the full story when a player carries 37-minute loads, guards the best player every night, and plays hurt all season.
Zach Lowe argued Jaylen Brown's salary was at least 50% of the reason for his trade, while Bill Simmons attributed 45% to the contract and 40% to self-awareness issues.
Zach Lowe estimated Jamal Murray's salary at approximately $50-57 million per year, raising the question of whether Denver would face similar trade-value concerns as Boston did with Jaylen Brown.
Paul George has made 8 All-Star teams and averaged 21-6-4 for his career with 39% from three, a resume Bill Simmons tried to use to justify the Celtics' trade.
Erling Haaland is the first striker Bill Simmons has ever watched who genuinely reminds him of a dominant basketball big man. Early '90s Shaq on bodies, Hakeem on footwork, young Shawn Kemp on headers — and then the Michael Myers post-goal face. He is making Norway a tournament dark horse.
The biggest what-if of Boston's offseason isn't the Finals MVP split — it's what if Tatum never got hurt during the Philly series. Lowe argues that's the event that catapulted Jaylen Brown into a new role, changed the chemistry equation, and ultimately made the trade feel necessary. Without the injury, maybe none of this happens.
The Philadelphia 76ers signed Anfernee Simons to a 2-year, $12.5 million deal, which Bill Simmons called a steal given Simons' abilities.
Simmons and Lowe make their Christmas Day game predictions: both agree on Celtics-Sixers as the noon opener, with Jaylen Brown making his Boston return. From there they diverge — Lowe wants Knicks-Heat in primetime, Simmons goes Spurs-Knicks early and OKC-Minnesota at 7:30. The wildcard is LeBron: wherever he signs, that game gets the 5 PM slot.
LeBron James chose to opt into his approximately $50 million contract rather than opt out and pursue a more ideal situation, a decision Zach Lowe and Bill Simmons questioned.
Bill Simmons' unsolicited advice to LeBron James: stop making decisions in July. Watch the season unfold from January, see who gets hurt, play golf for six months, and then pop in like Roger Clemens did with the Astros in the early 2000s. It maximizes attention and probably lands him on a better team.
Bill Simmons constructed the Mount Rushmore of 'oh no' NBA trades: Luka Doncic being number one by a mile, then Barkley to Phoenix for Hornacek/Lang/Perry, Harden to Houston, and Portland trading Moses Malone for $232,000 and one first-round pick. The Jaylen Brown trade earns a spot on the list — but it's nowhere near Luka territory.
At 12:30 AM, Bill Simmons convinced Zach Lowe he had attended Taylor Swift and Travis Kelce's wedding by dropping just enough detail to seem credible — Adam Sandler officiated, no tables, food courts everywhere, 1,500 people. Lowe was almost asking who his plus-one was before Simmons came clean.
A Kings fan named Sherb has posted the same month-by-month emotional timeline every year for five years, and it keeps coming true. October: we're gonna be good. November: we suck. August: Summer League bro our guys look sick. September: undefeated in preseason, question mark 5-seed. It is a masterpiece of sports misery.
No indexed bits in this chapter.
Four days after the Jaylen Brown trade, the consensus across the NBA is unanimous: nobody thinks it was good for Boston. The return was surprisingly low even accounting for known skepticism about Brown's value, and the only explanation that makes sense is the bridge was burned past the point of no return.
After Croatia had a goal disallowed by VAR in the final seconds of their World Cup exit, Zach Lowe declared war on replay technology across all sports. He doesn't want to watch NBA refs huddle anymore, he doesn't want soccer's VAR hair-follicle offside checks — he wants results to stand on the field, full stop.
Bill Simmons revealed he was coming out of anesthesia when his wife broke the Jaylen Brown trade news to him. He literally could not process it. Zach Lowe adds that multiple NBA executives called him that day asking 'Is Bill okay?' — and their reactions upon finding out where Simmons was were described as the most gleeful laughing he'd ever heard from grizzled veteran league men.
This episode
Factual claims made this episode, and whether a source was named.
Mexico had not lost a meaningful international home game in approximately 13 years before England's 3-2 win at Azteca in the 2026 World Cup.
Paul George averaged 23 points, 6 rebounds, and 5 assists per game with 39% from three over his 5 seasons with the Los Angeles Clippers.
Paul George had a 25-game drug suspension and then averaged 21 points per game on 42% from three in his final 10 games of the season.
Jaylen Brown finished 6th in MVP voting and made All-NBA in the 2024-25 season.
Jaylen Brown's salary escalates to $57M, $62M, and $66M over the remaining years of his contract.
The NBA salary cap stayed flat at approximately $58 million for 3-4 consecutive years during the late 2000s.
The Boston Celtics won 56 regular season games in 2024-25.
Philly traded the number 1 pick in 1986 for Roy Hinson and $750,000, missing out on Brad Daugherty.
Portland traded Moses Malone for one Buffalo first-round pick and $232,000, and Buffalo then flipped him for two number 1 picks six days later.
An anonymous NBA analytics executive reportedly graded Jaylen Brown as not one of the 50 best players in the league or not a top-7 player on a typical NBA team.
Bronny James earns approximately $2.2 million in his NBA contract.
Jamal Murray's salary is approximately $54-57 million per year.
Michelob Ultra is giving away $1 million in FIFA World Cup 26 tickets and prizes through its Superior Access promotion.
Paul George made 8 NBA All-Star teams and was 3rd in MVP voting in 2019.
Podcast P (Paul George's podcast) has gone dormant since July 2025.
This episode
Boston Celtics star traded to the Philadelphia 76ers in a deal that sent Paul George and picks to Boston, generating widespread league-wide controversy.
Veteran NBA forward acquired by Boston in the Jaylen Brown trade; Bill Simmons struggled to rationalize his value to the Celtics.
The 2026 FIFA World Cup being hosted across the US, Canada, and Mexico; a central topic of the episode's opening segment.
NBA superstar whose free agency destination is a major topic of speculation, with Golden State, Cleveland, Minnesota, and Denver all discussed as possible landing spots.
Boston Celtics star whose injury during the Philly playoff series and subsequent absence from Game 7 is cited as a catalyst for the Jaylen Brown trade.
Boston Celtics president of basketball operations who orchestrated the Jaylen Brown trade, defended somewhat by his strong organizational reputation.
Norway's striker in the 2026 World Cup, described by Bill Simmons as the first soccer player who reminds him of a dominant NBA big man.
Philadelphia 76ers center whose injury history raises questions about whether the Jaylen Brown-Maxey-Embiid trio can stay healthy through a playoff run.
Referenced as the top 'oh no' NBA trade — his move from Dallas to the Lakers is described as orders-of-magnitude worse than the Jaylen Brown trade.
Philadelphia 76ers point guard described by Bill Simmons as the true leader of the Sixers, whose team dynamic with incoming Jaylen Brown will be closely watched.
Top NBA draft pick for the Dallas Mavericks, referenced in a listener question about whether the Celtics are clearing cap space to eventually acquire him in 2028.
Denver Nuggets star repeatedly cited as an ideal LeBron James teammate; Bill Simmons described a potential LeBron-Jokic pairing as a 'weird movie' with two stars you can't believe are in the same film.
England midfielder praised by both hosts as the standout athlete of the England vs Mexico match at Azteca.
France's star forward described as one of the two most memorable players in the 2026 World Cup through the episode's recording date.
Argentina's legendary forward called the current tournament MVP by Bill Simmons, described as having the highest approval rating of any team sport athlete at the moment.
NBA franchise at the center of the episode's main discussion after trading Jaylen Brown to Philadelphia in a widely criticized move.
NBA franchise that acquired Jaylen Brown from Boston; Bill Simmons expressed optimism about their trio of Brown, Maxey, and Embiid.
Mexico City's iconic soccer stadium, described by Bill Simmons as the most intimidating sports venue he's ever attended, hosting England's dramatic 3-2 win over Mexico.
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