Skip to main content

Bill Simmons' wild Jaylen Brown trade idea comes with major risk

The assumption is that if the Celtics trade Jaylen Brown, it would be for a star like Giannis, but Bill Simmons thinks the opposite is actually true.
May 2, 2026; Boston, Massachusetts, USA; Boston Celtics guard Jaylen Brown (7) on the court before game seven of the first round of the 2026 NBA Playoffs against the Philadelphia 76ers at TD Garden. Mandatory Credit: Winslow Townson-Imagn Images
May 2, 2026; Boston, Massachusetts, USA; Boston Celtics guard Jaylen Brown (7) on the court before game seven of the first round of the 2026 NBA Playoffs against the Philadelphia 76ers at TD Garden. Mandatory Credit: Winslow Townson-Imagn Images | Winslow Townson-Imagn Images

One of the most well-known and well-connected Celtics fans out there, Bill Simmons, has been talking about every possible trade rumor since the season ended in Game 7 against the 76ers. He has pored over every angle of a potential Giannis trade, a potential Jaylen Brown trade, and has often mentioned Trey Murphy III as an intriguing target.

On his Wednesday night podcast, he went a step further, claiming that if the team does trade Brown this summer, he doesn’t believe it will be for a big-money star like Giannis. Instead, he stated that the goal would be to avoid having the two supermax contracts in Brown and Jayson Tatum, and to spread the money out across multiple players.

Simmons thinks Celtics will only trade JB to gain flexibility

His theory is that the Celtics will have two of the seven highest-paid players in the league next year and may decide that’s not sustainable for building a true contender. He suggested a trade where they send JB to New Orleans and get back Murphy III, Yves Missi, Herb Jones, a 2030 swap with the Pelicans, plus Cam Johnson and the 26th overall pick this year from Denver, with Sam Hauser and pick 40 heading to the Nuggets.

Simmons explained that he doesn’t think the Celtics want another big contract, like a Giannis, but they want to split JB’s deal into a bunch of players like this, creating flexibility to make more moves going forward, even mentioning the idea of packaging some of the new assets to move up in the draft.

This was just a fake trade that Bill made up, but there’s obviously plenty of smoke around this situation, and it seems clear that he’s in on this type of idea, spreading JB’s contract out and building a deep roster around Tatum with maximum flexibility moving forward.

Celtics are already flush with young role players on great deals

It’s a reasonable idea, but also a risky one. Trading a known commodity like Brown, who fits perfectly in Boston and has already won a Finals MVP, is a scary proposition, and there’s no guarantee that they’ll ever be able to put as good a player, or supporting cast, next to JT. 

Furthermore, the main problem with this idea is that the Celtics already have great young role players in spades, and they are all on great contracts. Would guys like Murphy, Jones, and Johnson be upgrades? Sure. But the Celtics are already flush with two-way wings in Baylor Scheierman, Hugo Gonzalez, Jordan Walsh, and Ron Harper Jr., who are on minimum deals.

Those guys have earned more playing time, and their value contracts allow the team to splurge on elite talent, like Brown. That’s why this doesn’t make a lot of sense to me. If you’re moving for a true top-line guy like Giannis, because you think he fits better and helps you raise a banner, so be it. But the Celtics have done an incredible job building on the margins, and they should be looking to build on that advantage. This kind of move would appear to do the opposite, and it feels like a waste of the job they’ve done building out the roster the last few years.

Add us as a preferred source on Google

Loading recommendations... Please wait while we load personalized content recommendations