Celtics Reportedly Have Explored Flipping Anfernee Simons After Jrue Holiday Trade

The Boston Celtics acquired Anfernee Simons as part of the Jrue Holiday trade, but the veteran guard may be on the move yet again.

The Athletic's Jay King reported Friday that "the Celtics have explored the idea of flipping Simons’ $27.7 million expiring contract, according to league sources."

He added: "In such a move, they would be aiming to accomplish two organizational directives Brad Stevens emphasized after the first round of the NBA Draft on Wednesday: regaining more roster flexibility and setting up a path to retain free agents Luke Kornet and Al Horford."

The news comes after an NBA personnel executive reportedly told Steve Bulpett of Heavy that "Boston's still out there talking trade, and [Simons] could be gone if the right move comes along."

In theory, Simons is a solid enough fit for the Celtics. He averaged 19.3 points and 4.8 assists per game for the Portland Trail Blazers last season across 70 games, shooting 36.3 percent from three. He's a solid perimeter shooter, hitting on 38.1 percent of his three-point attempts in his career, which should play well in Joe Mazzulla's system.

The Celtics will be without Jayson Tatum for most, if not all, of the 2025-26 season, however, as he recovers from a torn Achilles. Boston seems likely to keep the trio of Tatum, Jaylen Brown and Derrick White intact, but adding more moves with future seasons in mind could make sense.

The Celtics already got themselves under the second apron by trading Holiday and Kristaps Porziņģis. Any additional deals would hardly be a surprise, including another trade that reroutes Simons.