The Boston Celtics are poised to make significant roster changes this offseason, with a clear focus on shedding salary. One of the most likely candidates to be traded is Jrue Holiday, given his age and substantial contract. While Holiday has been a key piece in Boston’s recent success, moving him could free up cap space and reshape the team’s future. If the Celtics do trade Holiday, here are five players who could step into his starting role, each bringing a mix of promise and uncertainty that could leave fans torn between excitement and concern.
1. Marcus Smart
A potential homecoming for Marcus Smart could stir emotions among Celtics fans. The former Boston point guard, traded to the Grizzlies to make room for Holiday and later moved to the Washington Wizards, might be available again this summer. Smart’s gritty defense and fan-favorite status make him an appealing option, but his injury history—playing just 64 games over the last two seasons—raises red flags. With only one year left on his relatively affordable contract, a three-team trade could bring Smart back while helping Boston cut costs. Fans might cheer the return of a beloved player, but his health and limited long-term commitment could spark worry.
2. Mike Conley
For a short-term solution, Mike Conley could be a savvy pickup. The veteran point guard, set to earn $10.4 million next season on an expiring contract, offers leadership and solid offensive play. With Jayson Tatum expected to miss most of the 2025-26 season, Conley could stabilize the backcourt while mentoring younger players. However, the Timberwolves would need to include additional salary to match Holiday’s contract, and Conley’s age (38 by next season) and declining defensive ability might not inspire confidence for a championship push. Fans may appreciate his experience but question whether he’s enough to keep Boston competitive.
3. Damian Lillard
If the Celtics are willing to think long-term, a blockbuster trade involving both Holiday and Kristaps Porzingis for Damian Lillard could be on the table. Lillard’s contract aligns closely with the combined salaries of Holiday and Porzingis, making the deal feasible, though it wouldn’t immediately reduce Boston’s payroll. Lillard’s torn Achilles means he’ll likely miss most of next season, but his elite scoring could elevate the Celtics in 2026-27 and beyond. Fans might be thrilled at the prospect of adding a superstar, but the injury risk and lack of immediate salary relief could temper their enthusiasm.
4. Fred VanVleet
Fred VanVleet, slated to earn $44.8 million next season on an expiring contract, presents another high-profile option. Trading Holiday for VanVleet, possibly with an additional small contract to balance the books, could appeal to both teams. Houston might value Holiday’s superior defensive skills, while Boston would gain a dynamic point guard with a short-term commitment. VanVleet’s offensive prowess is undeniable, but his hefty salary and inconsistent defense could leave fans uneasy about the trade’s long-term impact. The potential to shed his contract after next season might be a silver lining, but it’s a risky move.
5. Payton Pritchard
The simplest solution might already be on the roster: Payton Pritchard. The young guard has shown significant improvement, particularly on defense, addressing earlier concerns about his game. With one of the NBA’s most team-friendly contracts, Pritchard could seamlessly step into the starting role without disrupting Boston’s salary structure. Fans may cheer his ascension, given his growth and cost efficiency, but relying on a relatively unproven player in a high-stakes role could spark doubts about whether he’s ready to lead a contending team.
Each of these options brings unique strengths and risks, leaving Celtics fans in a state of cautious optimism. Whether it’s a nostalgic reunion with Smart, a short-term fix with Conley, a bold swing for Lillard, a calculated move for VanVleet, or a promotion for Pritchard, Boston’s next steps will shape the franchise’s trajectory for years to come.