Mar 30, 2025; New York, New York, USA; Portland Trail Blazers guard Anfernee Simons (1) is guarded by New York Knicks guard Landry Shamet (44) during the first half at Madison Square Garden. Mandatory Credit: Vincent Carchietta-Imagn Images Vincent Carchietta-Imagn Images

Former Blazers Guard Could Be Traded for Second Time This Offseason

Originally posted on Portland Trail Blazers on SI
By Ryan Stano | Last updated Jul 10, 2025 3:00 PM ET

The Portland Trail Blazers made the decision to trade Anfernee Simons to the Boston Celtics in exchange for Jrue Holiday. The Blazers briefly had Holiday before last season started before trading him to Boston.

Holiday will now play in Portland as the Blazers seek some players who have leadership and a track record of winning. Simons in Boston is a different story.

Almost immediately after being traded to the Celtics, NBA insiders wondered if he was there to stay or if he was going to get moved. The Celtics have seemingly answered that question.

More news: Deandre Ayton Gets Honest About Shortcomings With Trail Blazers

According to ESPN's Brian Windhorst on his podcast The Hoop Collective, the Celtics are actively trying to find somewhere to move Simons.

Celtics 'Actively Trying To Trade Anfernee Simons'https://t.co/A6gMzDlxib
— Sam Amico (@AmicoHoops) July 9, 2025

Simons has a lot of value in the NBA. Multiple teams reached out to Portland at the trade deadline to inquire about his availability at that time. The Blazers decided to try to make a run at the playoffs instead.

Boston must not want to pay his contract, either. Simons is owed $27.6 million this season, but he is on an expiring deal. The Celtics must want to extract whatever value they can from that.

It remains unclear with what teams the Celtics are engaged in trade talks regarding Simons. As Portland can attest, he is a player who can get hot in a hurry, especially from beyond the three-point arc.

Simons is best used as a sixth man on a contending team. That might be the best market for Boston to send him to as they canvass the rest of the league for a trade partner.

More news: Deandre Ayton Felt He Was 'Forgotten' While With Blazers

While Simons might not play for the Celtics, Holiday will certainly play for the Blazers. Whether he comes off the bench or starts remains to be seen. They have to figure that out before the season starts.

Portland was probably hoping they could get a little more for Simons when they unloaded him to Boston. Still, Holiday is a solid defensive player who can give them a lot of leadership.

This past season with Portland, Simons averaged 19.3 points, 2.7 rebounds, and 4.3 assists per game. He shot 42.6 percent from the field and 36.3 percent from three.

More news: Former Blazer Deandre Ayton Excited to Be With 'Winning Organization' in Lakers

For more news and notes on the Portland Trail Blazers, visit Portland Trail Blazers on SI.

This article first appeared on Portland Trail Blazers on SI and was syndicated with permission.

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