The Celtics have become a regular for making noise in the NBA offseason, but Boston could take it to another level this summer.
The championship window established by Brad Stevens and company seemingly closed with a second-round loss to the New York Knicks. The Celtics now carry a wildly expensive roster, and their best player very well could miss the entire 2025-26 season. All things considered, it wouldn’t be shocking if Boston blows it up in the coming months.
Bill Simmons was thinking in that direction on the latest episode of his self-titled podcast for The Ringer. The longtime Celtics diehard put together a hypothetical deal involving the Houston Rockets, who previously were speculated to be a potential offseason trade partner for Boston.
“Looking at Houston, ‘We’ll take Jaylen (Brown) and Jrue (Holiday). Then we’ll give you (Fred) VanVleet back and Jabari (Smith Jr.) and (Tari) Eason, and we’ll give you the 10th pick. You’ll save, like, $20 million, we can make it work with our cap,'” Simmons said. “That gets you under the second apron, right? I think they would have to think about deals like that.”
The Celtics seem very likely to move Holiday, who turns 35 next month and has $104.4 million left on his contract, should he pick up his $37.2 million player option for the 2027-28 season. Brown has over $235 million left on his deal, but at only 28 years old, Boston might view him as a key player to build around in the new era.
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But as Simmons noted, Stevens and his team probably will need to at least think about any offers that come their way this summer.