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Bill Simmons believes the Celtics are still going to try to trade Jaylen Brown, despite failing to land Giannis Antetokounmpo

The Boston Celtics endured a hectic start to the week, as they went from emerging as the favorite to land Giannis Antetokounmpo in a trade with the Milwaukee Bucks to missing out on him at the last minute, with the Miami Heat swooping in to land him. The C’s are now left picking up the pieces on this failed trade, with all eyes turning to Jaylen Brown.

The main reason Boston suddenly found itself at the center of trade talks for Antetokounmpo was because of its willingness to part ways with Brown. For the time being, though, he remains in town, making him perhaps the most intriguing trade candidate across the league. And while he didn’t get moved in this deal, Celtics insider Bill Simmons still believes that he will be playing another team at the start of the upcoming season.

Bill Simmons Gets Brutally Honest on Jaylen Brown’s Future with the Celtics

The C’s were a tepid suitor for Antetokounmpo throughout his trade saga, but on the final day of the action, they appeared to emerge as the frontrunners for his services. The front office’s willingness to include Brown in its offer for Antetokounmpo changed everything and made it clear that the team needed to land “The Greek Freak” in order to avoid an awkward situation with one of its longtime stars.

Well, that’s the situation the team is staring at right now. This isn’t the first time Brown has seen his name pop up in trade rumors, but this was the most direct the team has been when it comes to its quest to move on from him. Now that Antetokounmpo is headed to Miami, nobody really knows what the future holds for Brown.

The team could try to smooth things over with him, or it could continue exploring trades for him. Teams across the league are certainly going to be interested in potentially swinging a deal for Brown, regardless of Boston’s interest level in trading him. And while the team could potentially hold onto him, Simmons isn’t convinced that’s how things will play out.

“I personally do not think they would have entertained this at the end of the season,” Simmons said on “The Bill Simmons Podcast.” “I think something definitely shifted as we went along, and I’m not convinced he’s going to be on the team in October. I would say it’s 50/50.”

What Should the Celtics Do with Jaylen Brown?

GettyBOSTON, MASSACHUSETTS – MARCH 25: Jaylen Brown #7 of the Boston Celtics looks on during the second half against the Oklahoma City Thunder at TD Garden on March 25, 2026 in Boston, Massachusetts. The Celtics defeat the Thunder 119-109. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Maddie Meyer/Getty Images)

If Brown’s status with the Celtics wasn’t already up in the air, it certainly is now. He’s already made a handful of questionable comments since the team’s elimination from the playoffs, and reports indicate he would be open to landing with a new team this offseason. That was all contingent on him being dealt to the Bucks in exchange for Antetokounmpo, though.

Now that he is off the board, it’s tough to find another trade in which Boston would benefit from moving on from Brown. The problem is that, if he’s upset with his name popping up in these trade rumors, the front office may have no choice but to send him to a new team. Brown didn’t get traded for Antetokounmpo, but now that he’s with the Heat, the Celtics star has quickly become the most enticing trade candidate in the NBA.