The Boston Celtics are staring down an offseason of tough decisions after a disappointing playoff run exposed a glaring weakness: their guard depth. One potential solution? Reuniting with a familiar face.

According to Boston Globe columnist Gary Washburn, the Celtics should strongly consider bringing back guard Anfernee Simons in free agency. "I would bring Anfernee back on the mid-level," Washburn said on The Garden Report on CLNS. Simons, who was traded at the deadline for center Nikola Vucevic, could be the spark Boston needs off the bench.

Simons thrived as the Celtics' sixth man for much of the season, stepping up when Jayson Tatum was sidelined and Payton Pritchard moved into the starting lineup. In 49 games with Boston, he averaged 14.2 points, 2.4 rebounds, and 2.4 assists in just under 25 minutes per game—while shooting a crisp 40% from three-point range. That kind of perimeter shooting was exactly what the Celtics lacked in the postseason.

He also made history in a Celtics uniform, breaking the franchise's record for points off the bench in a road game by dropping 39 on the Miami Heat in their own building.

After the trade to Chicago, Simons actually elevated his game, posting 15.2 points, 2.8 rebounds, and three assists per game in just over 28 minutes—before a fractured wrist cut his season short.

The logic for a reunion is simple. Outside of Pritchard, Boston's guard rotation looks shaky. Derrick White, once a reliable two-way presence, showed signs of offensive decline during the playoffs. Simons would not only fill that gap but also bring youth, scoring punch, and financial flexibility. He'd likely come cheaper than White, giving the Celtics options as they reshape their roster.

For a team that prides itself on depth, bringing Simons back could be the move that keeps Boston's championship window wide open.