The Boston Celtics shocked the NBA when they traded Jaylen Brown to their longtime rival, the Philadelphia 76ers, this offseason. Not only was Brown’s landing spot a shock, but the return for Brown, which saw the C’s land Paul George, in addition to a pair of first and second-round picks, was seen as relatively lackluster.
Many folks figured that, if Brown was going to get traded, he’d land with a team that would view him as their unquestioned leader. Instead, he’s on a loaded Philadelphia team, and if you ask Celtics insider Bill Simmons, he believes that Brown is only the fourth-best player on the Sixers’ roster currently.
Bill Simmons Hits Jaylen Brown with Harsh Reality
Brown enjoyed a lot of success during his time with Boston (after all, he was the 2024 NBA Finals MVP), but from an individual perspective, the 2025-26 campaign was the best year of his career. With Jayson Tatum missing most of the year recovering from a torn Achilles tendon, Brown put together an MVP-caliber season as the focal point of the C’s offense (28.7 PPG, 6.9 RPG, 5.1 APG, 47.7 FG%).
For years, folks had wondered whether Brown could eventually sour on the idea of working as the 1B to Tatum’s 1A in Boston. While he never officially requested a trade out of town, the understanding was that Brown was open to the idea of starting fresh with a new team, with the idea being he’d finally get a shot to prove he could be a de facto superstar player.
Instead, Brown landed with a team that already featured Joel Embiid and Tyrese Maxey and has since gone on to sign LeBron James in free agency. That is a loaded team, and while they should contend for a title, there are a lot of egos to balance here. Simmons took an immediate opportunity to fan the flames, as he claimed Brown is the fourth-best player on this team behind Embiid, Maxey, and James.
“I don’t know if this is the best situation for him in Philly, but I guess we’ll find out,” Simmons admitted on “The Bill Simmons Podcast.” “He went from, ‘It’s time for me to have my own team,’ to him being the fourth most important person on this team … He’s basically going to have to be their Derrick White.”
Celtics Hoping Jaylen Brown Trade Doesn’t Come Back to Bite Them
GettyPHILADELPHIA, PENNSYLVANIA – APRIL 26: Jaylen Brown #7 of the Boston Celtics looks on during warmups before game four of the Eastern Conference first round playoffs against the Philadelphia 76ers at Xfinity Mobile Arena on April 26, 2026 in Philadelphia, Pennsylvania. 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 Emilee Chinn/Getty Images)
There’s no doubt that this is an extremely risky move for the Celtics. Trading Brown after the best season of his career is such a minimal return, and while the front office gave itself some financial flexibility moving forward, it’s still very tough to justify this move. If Brown immediately helps Philadelphia win a championship, Boston will look even more foolish than it already does.
And yet, there are a lot of ways this could blow up in the Sixers’ faces, which is precisely what the C’s are hoping will happen. Their championship window is open, but it isn’t going to last long before issues begin popping up. The Celtics still have a talented team at their disposal, but now that Brown is gone, there are some serious questions surrounding this team that could be exacerbated if Philly goes on to make a title run.
Celtics Insider Takes Shot at Jaylen Brown After Sixers Trade