Boston sports fans have seen this movie before. A beloved star leaves town. The franchise that let him go spends decades wondering what could have been. And now, with the Celtics shipping Jaylen Brown to the Philadelphia 76ers, one analyst is drawing a direct line to the most painful trade in Boston history.
Marc Spears of Andscape compared the Brown deal to the Red Sox selling Babe Ruth to the Yankees in 1919. He said it on ESPN, via Brian Windhorst, and then posted it on X.
“There was the Babe Ruth trade out of Boston and then this is probably next,” Spears wrote.
That’s a heavy comparison. Ruth wasn’t just a good player. He was a historically dominant pitcher who threw 29 2/3 scoreless innings across the 1916 and 1918 World Series. Then in 1919 he hit 29 home runs, a number nobody had ever touched. He wanted to play the outfield full time. Red Sox owner Harry Frazee, who also produced Broadway shows, sold him to New York for $100,000.
The Curse of the Bambino, revisited?
Ruth became the defining athlete of the 1920s. The Yankees won 26 championships over the next eight decades. The Red Sox went 86 years without winning a single one. Fans called it the Curse of the Bambino, and it wasn’t broken until 2004.
Now, is Brown really comparable to Ruth? In one sense, no. Ruth changed baseball itself. Brown is a great two-way wing who won Finals MVP in 2024 when the Celtics finally got back on top. He spent 10 years in Boston, from 2016 to 2026, and made five All-Star teams. That’s a real career. But Ruth was an epochal force.
The comparison is about what happens next for the Celtics. If Philly wins multiple titles with Brown and Boston spends a decade chasing its own tail, people will talk about this deal the way they talk about Ruth to the Yankees. That’s the fear. That’s the weight Spears is putting on it.
For now, the Celtics are left without a familiar face and a fan favorite. Brown helped carry the franchise to its first championship since 2008. And the Sixers just got a proven winner entering his prime.
Bostonians have plenty of time to think about what that means. The last time a Boston team traded a star like this, the city felt it for almost a century.

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