The Boston Celtics, fresh off a stunning first-round playoff exit, appear ready to blow up their championship core. According to discussions on The Bill Simmons Podcast, the franchise is seriously weighing a blockbuster trade that would send All-Star Jaylen Brown to the Milwaukee Bucks in exchange for two-time MVP Giannis Antetokounmpo — a move that would send shockwaves across the NBA.
Bill Simmons and Zach Lowe broke down the difficult financial and competitive realities facing Boston this offseason. With Brown due $57 million, $61 million, and $65 million over the next three seasons — closely mirroring Jayson Tatum’s $58 million, $62 million, and $67 million deals — the Celtics are staring down an enormous luxury tax bill for two max-salaried wings.
“This would be the time to trade him right now,” Simmons said, highlighting the urgency driven by the contracts. The podcast explored multiple suitors, with the Bucks emerging as the marquee destination. Simmons envisioned a deal in which Brown heads to Milwaukee (or a third team, such as the Atlanta Hawks, where Brown is from), with assets flowing back to the Bucks to facilitate Giannis landing in Boston.
The scenario would instantly reshape the Eastern Conference. Pairing Tatum with Antetokounmpo would create one of the most physically dominant duos in NBA history, while giving the Celtics a new superstar centerpiece less tied to the recent playoff disappointments.
Yet the potential departure of Brown carries deep emotional weight. Simmons expressed hope that Brown and Tatum — teammates who reached two NBA Finals (2022 and 2024) and won a title together in 2024 — could spend their entire careers together in Boston. That sentiment, however, now clashes with on-court reality after the Celtics surrendered a 3-1 series lead to the No. 7 seed Philadelphia 76ers.
“There is also the possibility that Brown asks out,” Simmons noted. Having played second fiddle to Tatum for nearly a decade, Brown could seek a larger role elsewhere. “We’ve seen weirder things in the NBA than Jaylen Brown deciding, ‘I’d like my own team now.’”
Brown’s recent comments have only fueled speculation. In a post-elimination Twitch livestream, he declared the 2025-26 season his favorite of his professional career — this despite the first-round collapse and coming less than two years after claiming NBA Finals MVP honors. With Tatum sidelined for much of the year, Brown posted career highs across the board: 28.7 points, 6.9 rebounds, and 5.1 assists per game on 21.7 field goal attempts. He earned his fifth All-Star selection and is poised for another All-NBA nod.
“I wish we trusted that style of play a little bit more,” Brown said of the regular-season approach that unlocked his best basketball, before playoff rotations altered the formula.
As the Celtics sit at a crossroads, front-office conversations are reportedly happening in “dark, depressing rooms,” per Simmons. Trading a homegrown star like Brown for a transcendent talent like Antetokounmpo would represent a massive gamble — one that prioritizes immediate contention windows and financial flexibility over continuity.
Whether this blockbuster materializes remains to be seen. But after a bitter early exit, Boston’s willingness to entertain moving Jaylen Brown signals a franchise prepared to do whatever it takes to return to title contention — even if it means saying goodbye to one of its cornerstones. The NBA landscape could look dramatically different by the start of next season.