Boston Celtics shopping Anfernee Simons, interested in free agent Ben Simmons

The Boston Celtics are trying to trade Anfernee Simons while expressing interest in free agent guard Ben Simmons.

That’s according to NBA insider Marc Stein, who dropped a number of interesting nuggets in his latest Substack post.

He isn’t the first person to report that the Celtics are shopping Simons with ESPN’s Brian Windhorst also on the case.

Earlier this month, Boston sent Jrue Holiday to the Portland Trail Blazers for Simons but it doesn’t seem like the 26-year-old features in GM Brad Stevens’ long-term plans.

Simons is no doubt a capable player who offers a dynamic playmaking threat and dangerous shooting, averaging 19.3 points and 4.8 assists last season – but he’s graded as a poor defender throughout his career and that’s a red flag in Joe Mazzulla’s system.

It isn’t a complete disaster if Boston has to keep him as he’s on an expiring contract so the salary will be off the books by the time Jayson Tatum returns but the team certainly wants to pay as little tax as possible until that happens.

Tatum tore his achilles in the Eastern Conference semifinals against the New York Knicks and is expected to miss the entirety of the upcoming campaign.

Bookmakers are predicting a down year for the Celtics in 2025-26, whose win total has been set at 43.5 after winning 61 games in 2024-25 and 64 in 2023-24.

As mentioned above, Holiday is out the door – as is Kristaps Porzingis and both Al Horford and Luke Kornet are not returning.

That has opened up the potential of a few additions in free agency, with Ben Simmons’ name believed to be on Boston’s radar according to Stein.

Simmons was the first overall pick in the 2016 NBA Draft, enjoying a sparkling start to his career in Philadelphia with three All-Star selections, All-NBA Third Team honors and two appearances on the All-Defensive First Team.

Everything went downhill after he passed up an open dunk in the Sixers’ Game 7 defeat to the Atlanta Hawks in the 2021 Eastern Conference Finals, which teammate Joel Embiid and head coach Doc Rivers were publicly critical of.

He refused to play for the team, leading to a holdout and soon became the most-fined player in NBA history before he was traded to the Brooklyn Nets in February 2022.

Since then he has looked a shadow of his former self, struggling with chronic back injuries but there could be some upside to the signing on a veteran minimum contract.

There will be little to no expectations for the Celtics to challenge for the Eastern Conference crown and it gives the team a bit of freedom to experiment and see what could work.

Simmons could recoup some of his value at a big market team with low risk and a potentially high reward.

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