Jaylen Brown drafted 10 years ago
Bill Simmons noted the Celtics drafted Jaylen Brown roughly 10 years prior to the trade talks, emphasizing the deep loyalty Boston fans feel toward him.
Snapshot · The Bill Simmons Podcast
Giannis to Miami! An Urgent Gathering Pod With Chris Ryan and Justin Verrier
Explore episode
Jun 23, 2026
Where this was said
Why didn't the Giannis trade work for the Celtics?
At 27:50 · chapter starts 13:26
Simmons revisits his tweet insisting Hugo Olmstead wasn't genuinely included in Boston's trade offer for Giannis, drawing the parallel to how the Celtics once protected a raw Rajon Rondo in the Kevin Garnett trade — a move that looked right in hindsight. [1] — Bill Simmons "Bill Simmons declared he never believed Hugo Olmstead was included in any honest Boston offer, comparing it to the Rondo-for-KG trade where…" 41:16 At 20 years old and described as an asset even comparable to Khalil Ware, Hugo was simply not on the table. The conversation drifts into the 2026 NBA Draft: Simmons is live-streaming after the Boston pick, will be on Netflix, and is bullish on the draft being one of the better ones in recent memory. Verrier has talked himself into Boozer going early to Utah, though it seems to be cooling. Chris Ryan briefly assesses the Sixers ('Embiid availability dependent') and Portland's El Cheapo new owner, Tom Dundon, whose universal unpopularity among players and staff somehow makes the hosts think he'll do something splashy before the offseason ends.
Why Boston Didn't Blink on the Celtics Offer
Boston's offer was Jaylen Brown plus a couple of picks, and they never moved. Jalen was second-team All-NBA, younger and more durable than Giannis, and the Celtics simply weren't desperate enough to sweeten the deal. Brad Stevens held the line, and Milwaukee took Miami's Hail Mary instead.
Celtics were 3-11 vs. top-3 seeds cited by Stevens
Brad Stevens cited a 3-11 record against top-3 seeds in his postseason press conference as justification for needing a major roster upgrade, though Justin Verrier pushed back on the framing.
Jaylen Brown's Future in Boston: 50/50
Bill Simmons puts Jaylen Brown's odds of returning to Boston at 50/50. The small grievances have stacked up — the Twitch streams, the media spats, the 'this was my best year' quote. No smoking gun, just a thousand paper cuts. Something has clearly shifted.
Only 11 players: 125 playoff games + 19 PPG
Only 11 players in NBA history have played 125+ playoff games and averaged 19+ points, a club that includes Jaylen Brown alongside LeBron, Duncan, Kobe, and Magic.
Jaylen Brown's Historic Playoff Resume
Only 11 players in NBA history have played 125+ playoff games while averaging 19 points. The other 10 are LeBron, Duncan, Kawhi, Wade, Magic, Larry Bird, Kobe, Tatum, Worthy, and Klay Thompson. Jaylen Brown belongs in that conversation, and he's still getting better.
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