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Jaylen Brown called out by NBA host Justin Termine

The Boston Celtics are at a crossroads this offseason after losing in Round 1 of the playoffs, and superstar Jaylen Brown could be a trade candidate in the coming months.

Bill Simmons and Zach Lowe of The Ringer discussed that possibility on an episode of “The Bill Simmons Podcast” that aired on Sunday, May 3.

“This would be the time to trade him right now,” Simmons said. “Because [Brown’s yearly salary is] $57, $61 and $65 [million] the next three years, money-wise. Tatum’s [are] $58, $62 and $67 [million]. And if you’re gonna make a case to trade [Brown], it’s like, can you just afford two guys making that much money?”

Simmons and Lowe mentioned multiple teams that could prove trade suitors this summer, though the headliner was the Milwaukee Bucks with two-time MVP Giannis Antetokounmpo as the primary player coming back to Boston.

“I think [the Celtics] would be one of the contenders for Giannis, and I think Jaylen as an asset that either goes back to Milwaukee or goes to a third team, and then that team gives their stuff to Milwaukee would be how that trade goes,” Simmons continued. “A team like Atlanta, where [Brown is] from.”

Jaylen Brown Could Potentially Ask Celtics for Trade This Offseason

GettyJaylen Brown of the Boston Celtics.

Simmons added that he hopes Brown and Jayson Tatum, who have been to two NBA Finals together (2022 and 2024) and won a title together two years ago, play their entire careers alongside one another in Boston.

However, after dropping a 3-1 series lead to the No. 7 seed Philadelphia 76ers, Boston is in a position where it must consider the best path forward.

“I would understand if these are the kind of discussions they’re having in dark, depressing rooms right now,” Simmons continued.

There is also the possibility that Brown asks out after playing second fiddle to Tatum for essentially his entire 10-year NBA career.

“What if Jaylen Browns goest to the team and says, ‘It’s time, I want my own team,'” Simmons asked Lowe. “We’ve seen weirder things in the NBA than Jaylen Brown deciding, ‘I’d like my own team now.'”

Jaylen Brown Called Last Season His Favorite Year in NBA

GettyJaylen Brown of the Boston Celtics.

Brown noted on a controversial livestream following the Celtics’ disappointing first-round loss that the 2025-26 campaign was the favorite of his professional tenure thus far — a proclamation he made less than two years removed from winning a title and claiming Eastern Conference Finals MVP and NBA Finals MVP along the way.

“I wish we trusted that style of play a little bit more, but I know the playoffs kind of shifted our rotations and what we wanted to do,” Brown said on his Twitch stream. “But I am so proud, and it was my favorite year of my basketball career.”

In Tatum’s absence for the majority of the campaign, Brown averaged a career-high 28.7 points per game. He added career highs in rebounds (6.9) and assists (5.1) as well as field goal attempts (21.7).

Brown was an All-Star for the fifth time and is likely to be an All-NBA player, which will be just the second time he has accomplished that feat since joining the league in 2016.