The Boston Celtics may be looking to bring back a familiar face this offseason. According to a recent report from Celtics insider John Karalis, the team is considering a reunion with former guard Anfernee Simons in NBA free agency.

Simons, now 26, had a productive stint in Boston before being traded to the Chicago Bulls ahead of the 2026 NBA trade deadline. The deal, which sent Simons to Chicago in exchange for center Nikola Vucevic, was largely a wash for both sides. Simons played only six games with the Bulls due to injury, while Vucevic struggled to find his rhythm and missed time with a fractured finger.

With the Celtics expected to let Vucevic walk in free agency this summer, the door is open for a potential reunion with Simons. Karalis highlighted the guard as a realistic target, noting his offensive firepower and improved defensive play. "We know what he can bring offensively. He made some strides defensively, too. He’d probably take up most of, if not all of, the full mid-level," Karalis wrote.

During his time in Boston, Simons was a reliable contributor off the bench. Across 49 games, he averaged 14.2 points, 2.4 rebounds, and 2.4 assists in 24.5 minutes per game, while shooting an impressive .440 from the field, .395 from beyond the arc, and .889 from the free-throw line.

For Celtics fans, a return of Simons could provide the scoring punch and depth the team needs off the bench. As the offseason approaches, all eyes will be on Boston's front office to see if they make a move to bring back this familiar face.