Celtics Already Looking to Trade Guard Acquired in Jrue Holiday Deal

Boston acquired Anfernee Simons in the Holiday trade with the Trail Blazers.

The Celtics traded for Trail Blazers guard Anfernee Simons, but he may not ever appear for Boston if they can find a new trade suitor for him, according to ESPN's Brian Windhorst. / Winslow Townson-Imagn Images

The Celtics find themselves in a precarious position during the 2025 offseason: the team is in danger of going over the second apron of the salary cap—bringing on strict financial penalties and roster management limitations—but may not be in a position to contend for an NBA title while forward Jayson Tatum recovers from the torn Achilles he suffered during the playoffs.

That predicament informed Boston's offseason moves, which has featured a few notable trades of veteran contributors like Kristaps Porziņģis and Jrue Holiday. Holiday, a key piece of the 2024 title-winning team, was traded to the Portland Trail Blazers for Anfernee Simons, a 26-year-old score-first guard who looked to be a logical fit for a roster that will miss Tatum's scoring punch for most if not all of the season.

Simons is set to make around $27.7 million this season, the final year of a four-year contract. He is a bit cheaper than Holiday, who will make over $32 million in 2025–26 and has three years left on his deal. Even so, Simons's deal might still be too rich for the Celtics' blood given their salary cap situation. On Wednesday's edition of his podcast The Hoop Collective, ESPN's Brian Windhorst shared that other NBA teams say that Boston is actively looking to move Simons just days after the trade became official.

"They're trying ... I have talked to other teams who say that the Celtics are actively trying to trade Anfernee Simons. Whether they can or not is the other [question]."

Windhorst acknoweldged that Simons may fit what Boston needs if it wants to compete in a weak Eastern Conference. However, he believes the Celtics are instead trying to make this a "gap year," where they can reset their financial situation and be in a healthier position when Tatum is back close to 100% for 2026–27.

"People may say, 'Well why would the Celtics try to retrade Anfernee Simons? The guy is an electric scorer. They need something like that.' The answer is not because they don't like him. The answer is because they're trying to make it a true gap year," Windhorst said. "Get out of the tax, reset the repeater, reset the luxury tax, put themselves in a position to truly recover."

Boston currently has over $208 million in active salary cap allocations. The second apron is set at just over $207.8 million, per Spotrac.

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