Celtics urged to trade superstar wing this summer: 'Try to flip him'

The Boston Celtics' smartest move might be to trade one of their superstars this summer.

Many Celtics fans will condemn the thought of breaking up Jayson Tatum and Jaylen Brown. Still, the NBA's restrictive salary rules are making it tough for teams like Boston to keep two max players together for their entire careers while building a winning roster around those players.

The Celtics could keep Tatum and Brown together, but would that prevent GM Brad Stevens from building a deep roster around the duo moving forward?

On Sunday, The Ringer's Ryen Russillo and Bill Simmons spoke about Boston's conundrum on a new episode of The Bill Simmons Podcast.

Russillo asserted that trading Brown this summer would be a wise move for the Celtics.

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“Next year without Tatum is most likely a lost cause,” Russillo said.

“Jaylen … he’s still young enough, that I would try to flip him and look at next year as this gap year of (bringing) in some kind of assets to then reset … you’re gonna have to reset it around Tatum, anyway (in 2026).”

“You may be getting in front of something you probably have to do in 2026, anyway, and then resetting this thing around Tatum.”

“I’m serious — I think I would try to figure out a way to get a few assets back and reset the salary deck that way. You may be getting in front of something you have to do pretty soon, and there’s probably gonna be a lot less options (in 2026).”

Russillo's suggestion might rub a lot of Celtics fans the wrong way, particularly staunch Jaylen Brown supporters.

Brown's certainly done everything in his power to prove his loyalty to the Celtics organization, from delivering a championship in 2024 to playing through a torn meniscus in 2025.

It wouldn't be a basketball or emotional decision to part with Brown, but rather a cold-blooded financial choice.

Maybe Russillo's right -- the NBA's collective bargaining agreement and second apron limitations make trading Brown a healthier move for Boston than keeping him.

On the other hand, if there's any GM in the league who can figure out how to keep both The Jays and build a winner around them with the scraps of money leftover, it's Stevens.

There would be immense value in keeping Tatum and Brown together for the long haul. Fans want to see it, and this duo has already shown they can reach the promised land.

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