Bill Simmons has never been one to shy away from bold takes, but his latest trade proposal on The Bill Simmons Podcast might be one of his most radical ideas yet. With the Boston Celtics staring down a historic $500 million payroll and the looming second apron tax penalties, Simmons floated a trade scenario that would shake up two franchises and send two All-Star guards packing.
Proposed Trade Details:
Boston Celtics Receive: Fred VanVleet, Jabari Smith Jr., Tari Eason, and the No. 10 pick in the 2025 NBA Draft
Houston Rockets Receive: Jaylen Brown and Jrue Holiday
The Celtics are coming off a disappointing playoff exit, made worse by Jayson Tatum’s devastating Achilles injury, which could keep him out for the entire 2025-26 season.
With their championship window in jeopardy and a potentially record-setting tax bill looming, Boston faces a franchise-defining crossroads. Simmons’ trade idea reflects the difficult reality that the Celtics front office is now grappling with.
As constructed, the Celtics have already committed $227.8 million in player salaries for next season, according to Spotrac. That’s $73 million above the salary cap, $32 million beyond the first apron, and roughly $20 million past the second apron.
Factor in repeat offender tax penalties, and you’re looking at an eye-watering $500 million team cost. And that’s with Tatum unlikely to play.
Simmons' logic is blunt but compelling: If the Celtics are not title contenders next season due to Tatum’s injury, why pay a historically high tax bill? Trading Brown and Holiday would instantly cut salary, inject youth, and provide future assets.
From Houston’s side, the deal would signal a shift to full-on contention. The Rockets already have a treasure trove of young talent and cap flexibility. By acquiring Jaylen Brown, who just earned Finals MVP in 2024, and Jrue Holiday, a two-time champion and elite defender, Houston would leap from a playoff squad to a genuine title threat in the West.
Pairing Brown with Alperen Sengun and Jalen Green or potentially flipping Holiday in another deal gives them a veteran backbone without gutting their future entirely.
Meanwhile, Boston would receive Fred VanVleet, a championship point guard on a more manageable contract; Jabari Smith Jr., a 21-year-old stretch big with upside; Tari Eason, a tough-nosed defender; and the No. 10 pick in the draft to keep their prospect pipeline flowing.
VanVleet replaces Holiday’s leadership, while Smith and Eason add youth and length to the Celtics’ frontcourt. Crucially, it would also drag Boston below the second apron, allowing Brad Stevens to make other trades this summer without being handcuffed by the NBA’s new collective bargaining restrictions.
Of course, this move would mean punting on 2025-26 and possibly ending the Tatum-Brown era. But Simmons’ vision is clear: the Celtics regroup financially, retool around Tatum for 2026-27, and stay flexible for the long run.
It’s aggressive. It’s risky. But with a $500 million bill looming and a superstar sidelined, Bill Simmons might be onto something.
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