Snapshot · The Bill Simmons Podcast
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.
Where this was said
At 43:03 · chapter starts 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 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.
Despite months of meticulous preparation, Starter Story's initial launch attracted zero users — a humbling reminder that building alone guarantees nothing.
A single Reddit link post quickly drove 100 visitors to the Starter Story website, igniting the founder's belief in social traffic.
After reformatting content as a native self-post (no direct link spam), the post exploded with hundreds of upvotes and thousands of readers.
By posting again and again with the native-content strategy, the founder's posts repeatedly hit Reddit's front page, reaching millions of readers.
Before Reddit banned his domain, the founder converted his viral traffic into an email list of tens of thousands — a self-owned audience independent of Reddit.
Redditors eventually organized a petition to ban starterstory.com posts, effectively ending the Reddit growth channel — but the email list was already built.
The Reddit attention strategy ultimately served as the foundation for a million-dollar business, proving that free distribution channels can replace paid marketing.
The key tactic was keeping content fully on-platform (no direct link spam), then adding a small link at the post's end for users who wanted more.
With a thriving email list and a self-owned audience, the founder quit his six-figure New York City salary job to go all-in on Starter Story.
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