Mar 5, 2025; Boston, Massachusetts, USA; Boston Celtics guard Payton Pritchard (11) goes to the basket past Portland Trail Blazers guard Anfernee Simons (1) during the second half at TD Garden. Mandatory Credit: Winslow Townson-Imagn Images Winslow Townson-Imagn Images

Celtics’ $100 Million Guard Linked to Another East Rival in Trade

Originally posted on Boston Celtics on SI | By Ryan Stano | Last updated Aug 26, 2025 5:00 PM ET

The Boston Celtics have been trying to unload salary as much as possible in order to get under the second apron of the luxury tax. They are now much closer to getting under the luxury tax, period.

In order to achieve that goal, they still have to find a goal for guard Anfernee Simons, the player that the Celtics received in return for the Jrue Holiday trade.

Boston has been looking for a trade partner to send him off for quite a while. They may have finally found someone who is willing to bring him in.

More news: Celtics Rumors: East Rival Targeting Anfernee Simons in Potential Blockbuster Trade

It looks like a longtime Eastern Conference rival may be interested in bringing Simons aboard.

According to Sam Amico of Hoops Wire, the Milwaukee Bucks have been contemplating a possible Simons trade. Given that Milwaukee is without injured All-Star Damian Lillard after opting to stretch and waive his remaining money, the team could use a scoring point guard upgrade.

At this point, it's unclear what kind of trade would take place between the Celtics and Milwaukee. Nothing has been confirmed at this point.

Boston is still trying to find out who they can get in return for a trade. They don't want to have to include any draft capital in a Simons trade, but they might have to if they really want to get rid of him.

More news: Celtics’ Jaylen Brown Makes Promise to Fans Ahead of 2025-26 Season

Simons is a very good scorer who can certainly help the right team. Boston doesn't seem to be in contention for a championship next season without Jayson Tatum.

The Celtics should only trade Anfernee Simons if they don't plan to compete next year

Boston will be replacing three different starters next season due to trades they have made, as well as injuries. Getting Simons out of town would very much help their cap sheet.

The Celtics are going to try to compete for a championship again in 2026-27 when they are able to get Tatum back. If they don't plan on trying to make a deep playoff run, they should trade Simons.

Simons would fit well in Boston's offensive system, since he can get hot from beyond the 3-point line in a hurry. It doesn't look like the Celtics want to give him that chance.

Last year, Simons averaged 19.3 points, 2.7 rebounds, and 4.8 assists per game.