The Boston Celtics have been the NBA’s busiest team this offseason, navigating a financial tightrope with surgical precision. Faced with a looming salary cap crisis, GM Brad Stevens has made bold moves to shed significant payroll, ensuring the team avoids cap hell. However, these cost-cutting measures came at a steep price: a significant loss of talent. With superstar Jayson Tatum sidelined for the entire 2025-26 season due to an Achilles injury, the Celtics are bracing for a challenging year. But don’t expect Boston to wave the white flag. With a core of Jaylen Brown, Derrick White, Payton Pritchard, and Anfernee Simons, the Celtics are far from tanking—they’re gearing up to stay competitive in a relatively weak Eastern Conference.
To keep their playoff hopes alive, Stevens must make one more audacious move: trim the overcrowded center rotation and sign free agent Ben Simmons. This could be the blockbuster decision that keeps Boston relevant in a Tatum-less season.
Boston’s roster is currently packed with 14 players on guaranteed contracts, bolstered by the recent addition of Chris Boucher. Add in two-way players Max Shulga, Miles Norris, and Reggie Luis Jr., plus unsigned rookie Amari Williams, and the Celtics are at capacity. To make room for a game-changer like Simmons, someone has to go—and Xavier Tillman Sr. is the most likely candidate.
Tillman, a 26-year-old versatile big man, earns a modest $2.5 million for the 2025-26 season, making his contract an easy one to move. While his defensive prowess earned him a spot in Boston’s rotation, the arrival of Luka Garza, Boucher, and the emergence of Neemias Queta—along with rookie Amari Williams—has crowded the center position. Tillman’s offensive limitations further diminish his role on a team that needs spacing and scoring. Despite his youth and defensive upside, which could attract interest from other NBA teams, Tillman is the odd man out in Boston’s frontcourt.
By moving Tillman, Stevens can free up a roster spot and cap space to pursue a high-upside gamble that could redefine the Celtics’ season.
Enter Ben Simmons, the unsigned free agent whose unique skill set could be the spark Boston needs. Simmons, a former All-Star, brings elite defensive versatility that aligns perfectly with coach Joe Mazzulla’s system. Capable of guarding power forwards, centers, and even wings, Simmons would bolster a frontcourt depleted by Tatum’s absence and the roster overhaul. His ability to switch across multiple positions makes him an ideal fit for a team looking to stay scrappy and competitive.
Offensively, Simmons is not without his challenges. His reluctance to shoot and limited scoring ability require careful roster construction. However, Boston’s current lineup is tailor-made to mask these weaknesses. Surround Simmons with sharpshooters like Pritchard, Simons, White, and Sam Hauser, and his playmaking can shine. As a secondary ballhandler, Simmons can orchestrate the offense in short bursts, leveraging his vision and passing to create open looks for Boston’s shooters.
A one-year, team-friendly deal for Simmons makes perfect sense for a Celtics team in transition. Without championship expectations this season, Boston can afford to take a low-risk, high-reward swing on a player with Simmons’ upside. If he regains even a fraction of his former brilliance, the Celtics could surprise the Eastern Conference and secure a playoff spot.
The Celtics’ offseason has been defined by tough choices, but Stevens’ track record suggests he’s not afraid to make them. Trading Tillman’s modest contract to clear space for Simmons is the kind of calculated gamble that could keep Boston in the playoff hunt. In a weakened Eastern Conference, a lineup featuring Brown’s scoring, White’s two-way tenacity, Simons’ explosiveness, and Simmons’ defensive versatility could make waves.
This isn’t about chasing a title—it’s about staying relevant, developing talent, and setting the stage for Tatum’s return in 2026-27. Signing Ben Simmons could be the shocking blockbuster that keeps the Celtics’ competitive fire burning. Stevens has already proven he’s willing to make tough calls. Now, it’s time to make a bold one.