The Boston Celtics are entering a pivotal offseason, and all eyes are on Brad Stevens. After dismantling what was on track to be the most expensive roster in NBA history—a staggering $540 million—the front office has successfully shed roughly $350 million, pulling the team back under the luxury tax. This newfound financial flexibility gives Stevens more breathing room than ever before, and he’s already made it clear: the Celtics need to improve.

Following a playoff exit that left fans wanting more, Stevens didn’t mince words about the areas that need work. Now, the real action begins with the decisions he makes this summer. As the front office explores its options, the free-agent market is offering up a trip down memory lane, featuring some beloved former Celtics who could make a real difference in Boston’s title chase.

So, who should the Celtics consider bringing back? Let’s break down the most intriguing reunion candidates.

Anfernee Simons: The Shot Creator Boston Needs
In a league obsessed with analytics, it’s easy to forget the game’s simplest truth: you have to put the ball in the hoop. Anfernee Simons proved he can do just that—and in a variety of ways—during his brief stint in Boston last season. The Celtics struggled to find reliable offensive initiators, leaning heavily on Jaylen Brown, Derrick White, and Payton Pritchard. When Jayson Tatum returned, he was immediately thrust into a high-usage role. Simons, however, brought a steady scoring presence that the team desperately needed.

According to Basketball Reference, Simons posted a 23.7% usage rate, the third-highest on the team behind only Brown and Tatum. He averaged 14.3 points and 2.4 assists per game, consistently creating quality looks for himself. Even with that heavy workload, he managed a career-best 8.4% turnover rate. Better yet, he shot 42.9% on catch-and-shoot threes, proving he can thrive both on and off the ball. Stevens has emphasized the need for a greater margin for error next season, and adding a player with Simons’ offensive firepower is a direct way to raise the team’s floor.

Other Familiar Faces on the Market
The list of former Celtics hitting free agency this summer is a who’s who of fan favorites: Marcus Smart, Robert Williams III, Kristaps Porzingis, and Al Horford (who holds a player option). Each brings a unique skill set that could address specific needs. Smart’s tenacious defense and leadership are legendary in Boston. Williams III offers elite rim protection and lob threat energy. Porzingis provides floor-spacing size, and Horford’s veteran savvy remains invaluable.

Whether for nostalgia or real on-court impact, the Celtics have several paths to explore. Which reunion would you root for? The offseason is just getting started, and Boston’s front office has some serious decisions to make.