Colin Cowherd Says Celtics Selling Jaylen Brown Was a Chess Move. Not Everyone Agrees.

The Boston Celtics traded Jaylen Brown to the Philadelphia 76ers this week, and the internet basically melted down. Fans called it panic. Analysts gave it a D+. But Colin Cowherd sees it differently.

Cowherd, speaking on his show, argued that Celtics president Brad Stevens saw the new collective bargaining agreement coming like a freight train and got off the tracks before it hit him. Trading Brown wasn’t a mistake, Cowherd said. It was a chess move.

The deal sent Brown to Philly for multiple draft picks and veteran Paul George. On paper, Boston swapped a 29-point-per-game scorer in his prime for an older star and some futures. That’s the kind of move that gets a front office roasted on local radio for a decade if it doesn’t work.

ESPN’s Zach Kram wrote that the whole thing was baffling from start to finish. He pointed out that Boston has been the most successful franchise of the 2020s — first in regular-season wins, first in playoff wins, the only team to win a title and make another Finals — and now they’re voluntarily stepping back. He called it utterly strange.

And look, that’s fair. The Celtics just won a championship. They didn’t have to blow anything up. But Cowherd’s argument is that Stevens is looking at the new CBA rules — the harsher luxury tax penalties, the restrictions on high-spending teams — and deciding he’d rather retool now than get stuck later. That kind of long-term thinking doesn’t always sit well with fans who just want to feel good about next season.

Cowherd framed it as Stevens saying he won’t be the new NBA, meaning he won’t just run back the same expensive roster and hope for the best. He’s trying to restock while the market still values Brown. Whether that’s genius or delusion depends on what Boston does with those picks and how George fits. George is 36 and coming off another season where he missed games. That’s not nothing.

During the 2025-26 regular season, Brown averaged nearly 29 points for Boston. He was their second-best player on a title team. That doesn’t grow on trees. But the Celtics clearly decided they’d rather have flexibility than loyalty. Time will tell if they were right.

For now, Philadelphia just added an All-NBA wing to go with Embiid and Maxey. And Boston is holding draft picks and hoping the math works out. One of these teams is going to look very smart in two years. The other is going to hear about this trade every single day until they win again.