The Boston Celtics have a funny way of doing business. They trade for a player, use him for half a season, ship him out at the deadline, and then — just a few months later — consider bringing him back.
That’s the story of Anfernee Simons.
The 26-year-old guard arrived in Boston last summer as part of the Jrue Holiday trade. He played 49 games for the Celtics. He scored in double figures in 37 of them. He shot 39.5% from three. He drew praise from Joe Mazzulla for his improved defense.
Then, at the trade deadline, Boston shipped him to Chicago for Nikola Vucevic. The move helped the Celtics get below the luxury tax and add frontcourt size.
Now, according to Boston Herald reporter Zack Cox, a reunion could be on the table.
And it might make more sense now than it did the first time.
Anfernee Simons
Let me break down why Simons fits, why the Celtics should bring him back, and how his role in Boston could be completely different in a second stint.
The Simons Profile: A Scorer Who Can Shoot
Let me start with the player.
Anfernee Simons is 26 years old. He’s a 6-foot-3 guard with elite shooting ability and improving playmaking skills. He developed into a starter in Portland, averaging 19.3 points per game in 2024-25 after back-to-back 20-point seasons.
In his half-season with Boston, he averaged 14.2 points per game off the bench. He shot 39.5% from three. He was efficient. He was productive.
And then the Celtics traded him.
Why? Because they needed a center. Because they wanted to get below the luxury tax. Because Vucevic was available.
The move made sense at the time. But it also left a hole in Boston’s backcourt depth.
The Vucevic Trade: A Necessary Evil
Let me talk about the trade that sent Simons away.
The Celtics needed size. Nikola Vucevic was available. The Bulls were tanking. The deal worked financially — moving Simons’ $27.7 million salary helped Boston duck the luxury tax.
But here’s the thing: Vucevic was a healthy DNP in Game 7 against the Sixers. He barely played in the playoffs. The Celtics still lost in the first round.
So what did that trade actually accomplish?
Boston got below the tax line. That’s valuable. But they also lost a young, productive shooting guard who could have helped them in the postseason.
Now, with Vucevic likely gone in free agency, the Celtics have an opportunity to correct their mistake.
The Fit: Why Simons Works in Boston (the Second Time)
Let me talk about the basketball fit.
The Celtics’ offense is built on three-point shooting and ball movement. Simons is a career 38% shooter from deep. He can play off the ball. He can run pick-and-roll. He can create his own shot.
He’s exactly the kind of guard who thrives next to Jayson Tatum and Jaylen Brown.
In his first stint, Simons came off the bench behind Derrick White and Payton Pritchard. He didn’t complain. He played hard. He shot well. He was a professional.
But he never got a real chance to be a featured scorer. That could change in a second stint.
The Brown Trade Scenario: Why Simons Could Start
Boston Celtics forward Jaylen Brown
Let me address the elephant in the room.
Jaylen Brown’s name has been in trade rumors. If the Celtics move Brown for a superstar like Giannis Antetokounmpo, they’ll have a gaping hole at the guard position.
Derrick White is the starting point guard. Payton Pritchard is the backup. But behind them? There’s not much.
Anfernee Simons could step into that void. He could start alongside White. He could be the secondary scorer. He could take some of the playmaking pressure off Tatum.
Even if Brown stays, the Celtics need guard depth. Baylor Scheierman is a nice young player, but he’s not a proven scorer. Simons is.
The Contract: A Bargain Waiting to Happen
Let me get into the money.
Simons just finished a contract that paid him $27.7 million in the final year. That’s a lot. But Cox notes that he’ll “likely need to settle for less” on his next deal.
How much less? The non-taxpayer mid-level exception is roughly $15 million per year. The veteran minimum is much lower. Somewhere in between is realistic.
Simons is not a star. He’s not getting $30 million per year. But he’s also not a minimum-salary player. He’s a proven scorer who can shoot 40% from three.
If the Celtics can sign him for $10-15 million per year, that’s a bargain.
The Mazzulla Factor: ‘Frequent Praise for His Improved Defense’
Let me talk about the most surprising part of Cox’s report.
When Simons was in Boston, Joe Mazzulla praised his defense. That’s not something you hear often about Simons. In Portland, he was known as a scorer who struggled on that end.
But Mazzulla saw something different. He saw improvement. He saw effort. He saw a player who was buying into the system.
That matters. If Simons can be even an average defender, his value skyrockets. A 6-foot-3 guard who shoots 40% from three and holds his own on defense is a rotation player on any contender.
The Portland Years: What Simons Can Do as a Scorer
Let me remind you what Simons is capable of.
In Portland, before the Damian Lillard trade, Simons was putting up 20+ points per game as a starter. He was the focal point of the offense. He was running pick-and-roll. He was creating his own shot.
He won’t need to do that in Boston. But the fact that he can is important.
When Tatum and Brown are on the bench, the Celtics’ offense often stagnates. They need someone who can get a bucket. Simons can do that.
The Depth Chart: Where Would Simons Fit?
Let me map out the Celtics’ backcourt.
If Brown stays:
Starting guards: Derrick White, Jaylen Brown
Bench guards: Payton Pritchard, Anfernee Simons
Deep bench: Baylor Scheierman, JD Davison
That’s a solid rotation. Simons would be the sixth man — a scorer off the bench who can also play next to White or Pritchard in three-guard lineups.
If Brown is traded:
Starting guards: Derrick White, Anfernee Simons
Bench guards: Payton Pritchard, Baylor Scheierman
Deep bench: JD Davison
Simons would start. He’d be asked to score 15-18 points per night. He’d be a key piece of the offense.
Either way, there’s a role for him.
The Cost: What Would It Take to Sign Him?
Let me be realistic.
Simons will have other suitors. Teams with cap space — the Orlando Magic, the Detroit Pistons, the San Antonio Spurs — could offer him more than the Celtics can.
But Boston offers something those teams can’t: a chance to win. A chance to play in the playoffs. A chance to compete for a championship.
If Simons wants to win — and he’s said he does — he might take less money to come back to Boston.
Final Verdict: Bring Him Back
Here’s my honest take.
The Boston Celtics made a mistake when they traded Anfernee Simons. They needed a center, so they got Vucevic. Vucevic didn’t help them win. He was a DNP in Game 7.
Simons could have helped. He could have provided scoring off the bench. He could have taken pressure off Tatum and Brown.
Now the Celtics have a chance to correct that mistake.
Sign Simons in free agency. Bring him back on a team-friendly deal. Let him be the scorer off the bench that they’ve been missing.
He knows the system. He knows the coaches. He knows the players. He’s a familiar face who can contribute immediately.
The Celtics need shooting. They need guard depth. They need a player who can get a bucket when the offense stalls.
Anfernee Simons is that player.
One thing’s certain: The Celtics should not let the same player get away twice.