Celtics Insider Provides Update on Anfernee Simons Trade Rumors

Mar 30, 2025; New York, New York, USA: Portland Trail Blazers guard Anfernee Simons (1) dribbles during the first half against the New York Knicks at Madison Square Garden. Mandatory Credit: Vincent Carchietta-Imagn Images | Vincent Carchietta-Imagn Images

Do the Boston Celtics have an Anfernee Simons problem?

The club's new big-ticket guard acquisition, 26, represents its most valuable on-court haul following a flurry of cost-cutting trades this summer. Boston swapped out 35-year-old former championship guard Jrue Holiday, a six-time All-Defensive Teamer and two-time All-Star, in exchange for Simons' expiring deal.

Holiday is under contract for three more seasons at a pricier annual value, and Boston was looking to skirt the league's punitive second luxury tax apron this season, when the team doesn't expect to compete for a championship by offloading his money.

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The Celtics also traded away starting center Kristaps Porzingis, let his deep-bench backup Luke Kornet sign with the San Antonio Spurs in free agency, and appears set to let reserve big man Al Horford walk, too, although he has yet to sign with a new team.

Boston may face something of an uphill battle when it comes to potentially dealing Simons' expiring $27.7 million contract this season, Brian Robb of MassLive writes.

Simons Faces an Uncertain Trade Market

"It’s going to be based largely on his trade market around the league, in my opinion. The guard spot is very deep around the league and there simply aren’t a lot of teams in the market for a guy making [$27.7] million that wouldn’t start for most teams," Robb notes. "That could change if certain injuries hit but even then, the finances would need to make sense for Boston to make a deal... They aren’t going to want to take on unwanted long-term money in any deal for Simons and instead ideally would be cutting salary."

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Last season, Simons was shifting to a starting point guard role for the 36-46 Portland Trail Blazers, after having served as the club's starting shooting guard for years. In 70 healthy contests, the 6-foot-3 pro averaged 19.3 points on .426/.363/.902 shooting splits, 4.8 dimes, 2.7 boards, and 0.9 steals a night.

For now, the Celtics will need to figure out how to stagger Simons and Sixth Man of the Year point guard Payton Pritchard, who in the wake of Holiday's exit seems poised to move into that starting point guard role next to two-time All-Defensive Team guard Derrick White.

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