Anfernee Simons Reportedly Shopped by Celtics in NBA Trade Talks After Holiday Deal

The Boston Celtics are reportedly exploring the possibility of flipping guard Anfernee Simons after acquiring him in a trade that sent veteran guard Jrue Holiday to the Portland Trail Blazers this offseason.

Speaking Wednesday on his Brian Windhorst & The Hoop Collective podcast (h/t RealGM.com), ESPN NBA insider Brian Windhorst said the following about Simons and the Celtics: "I have talked to other teams who have said they are actively trying to trade Anfernee Simons. Whether they can or not is another [thing]."

Simons, 26, is about to enter his eighth NBA season, which also marks the final year of a four-year, $100 million contract he signed with the Blazers in 2022.

Originally selected 24th overall in the 2018 NBA draft, he has been a highly effective offensive player over the past four seasons after playing sparingly in his first three years in the league.

Simons has appeared in 235 games the past four years, averaging 19.9 points, 4.5 assists, 3.2 three-pointers made and 2.8 rebounds per contest, while shooting 43.6 percent from the field and 38.1 percent from beyond the arc.

Injuries have been a bit of an issue for him, as he has only reached the 70-game mark twice in his career and has never played in more than 70 games in a single season.

From 2021 to 2024, Simons missed 20 or more games in three straight seasons, which included sitting out 36 games in 2023-24.

He had a career year in 2023-24 in terms of his averages with 22.6 points, 5.5 assists, 3.6 rebounds and 3.4 three-pointers made per game, but he missed significant time with thumb and knee injuries.

He bounced back to match his career high with 70 games played last season, but Simons' numbers did take a step back to the tune of 19.3 points, 4.8 assists, 3.1 three-pointers made and 2.7 rebounds per contest.

The Celtics seemed poised to win multiple championships following their triumph in the 2024 NBA Finals, but things have changed quite a bit since then.

During the second round of the 2024-25 playoffs, superstar forward Jayson Tatum tore his Achilles, which is likely to cost him most, if not all, of the 2025-26 season.

That injury may have caused a philosophical shift, as the Celtics parted ways with multiple players who contributed to their most recent championship team, trading Holiday to Portland and Kristaps Porziņģis to the Atlanta Hawks.

Boston president of basketball operations Brad Stevens also told reporters this week it is "unlikely" the organization will retain free-agent big man Al Horford.

Taking the injured Tatum and the uncertain future of Simons out of the equation, the Celtics are currently set to enter next season with a core of Jaylen Brown, Derrick White and Payton Pritchard leading the way.

They have little in the way of quality frontcourt players, though, with Tatum on the shelf and both Porziņģis and Horford no longer in the fold.

That suggests the Celtics could look to move Simons out for a much-needed big, but if no team is interested in such a trade, head coach Joe Mazzulla may have to employ a small-ball approach next season.