The Boston Celtics are making waves in the NBA trade market, with Anfernee Simons at the center of a stunning proposed deal that could reshape their roster for the upcoming season. Fresh off a trade that saw Jrue Holiday head to the Portland Trail Blazers, Simons, now in the final year of his $27.6 million contract, might not stay in Boston for long. With the Celtics teetering on the edge of the second luxury tax apron, president of basketball operations Brad Stevens appears determined to keep the team financially flexible while bolstering their depth. Enter a blockbuster 2-for-1 trade proposal that could send Simons to the Washington Wizards and bring new talent to Boston.
A Strategic Trade to Duck the Luxury Tax
ClutchPoint’s Bailey Bassett has floated an intriguing trade idea that would help the Celtics avoid the restrictive second luxury tax apron while addressing key roster needs. The proposed deal is as follows:
Wizards receive: Anfernee Simons
Celtics receive: Corey Kispert, Richaun Holmes, two second-round picks
This trade would allow Boston to shed Simons’ hefty $27.6 million salary while bringing in two versatile players whose combined salaries—$13.97 million for Kispert and $13.28 million for Holmes—fit within the NBA’s strict salary-matching rules for second-apron teams. Alternatively, the deal could push Boston under the second apron entirely, granting them greater flexibility in future roster moves.
Bassett argues that both Kispert and Holmes could make an immediate impact. “Richaun Holmes is under contract for two more seasons, and Corey Kispert won’t hit the open market until after the 2028-29 season,” he noted. “Boston is particularly thin at the center position, so Holmes could have a big role with the team. Kispert, one of the NBA’s premier 3-point shooters, would also be an intriguing addition to space the floor for Jayson Tatum and Jaylen Brown.”
Holmes, a 31-year-old veteran, brings much-needed depth at center, especially after Boston parted ways with Kristaps Porzingis and Luke Kornet, with Al Horford’s future uncertain. Meanwhile, Kispert’s sharpshooting—consistently among the league’s best from beyond the arc—could provide the perimeter firepower Boston needs to maintain its high-octane offense.
Simons on the Move: A Mismatch in Boston?
Simons, acquired in the Holiday trade, is a dynamic scoring guard who fits seamlessly into Boston’s free-flowing offensive system. However, his defensive limitations and high-cost contract have sparked discussions about his long-term fit. According to ESPN’s Brian Windhorst on The Hoops Collective podcast, the Celtics are “actively” exploring trade options for Simons. “I’ve talked to other teams that have said the Celtics are actively trying to trade Anfernee Simons,” Windhorst revealed. “Whether they can or not is another thing.”
With the upcoming season focused on developing talent to complement superstars Jayson Tatum and Jaylen Brown, Stevens may see Simons as a luxury Boston can’t afford—both financially and stylistically. Flipping him for players like Kispert and Holmes, who offer cost-controlled contracts and specific skill sets, could align better with the Celtics’ long-term vision.
A Potential Reunion with Marcus Smart?
In another twist, Jake Weinbach reported via X that the Celtics could be in line for a reunion with fan favorite Marcus Smart. The Washington Wizards, now carrying 17 players on their active roster, are reportedly looking to offload veterans to prioritize younger talent. Weinbach noted, “A potential reunion between Marcus Smart and the Celtics would not be off the table. The Wizards would reportedly prefer to send Smart to a desired location.”
Smart, known for his tenacious defense and playmaking, could slide into a significant role in Boston’s second unit, bringing the grit and heart that defined his earlier tenure with the team. While it’s unclear if Stevens would pursue this move, Smart’s return would electrify the TD Garden faithful and add a defensive anchor to a roster in transition.
What’s Next for Boston?
As the Celtics navigate the complexities of the luxury tax and roster construction, Stevens’ aggressive approach signals a commitment to keeping Boston competitive while staying financially savvy. Trading Simons, a talented but expensive guard, for Kispert’s shooting and Holmes’ frontcourt presence could be a masterstroke. Add in the possibility of reuniting with Smart, and Boston’s offseason could go from intriguing to downright explosive.
With training camp on the horizon, all eyes are on Stevens to see how he shapes the roster around Tatum and Brown. One thing is clear: the Celtics are not standing pat, and this blockbuster trade proposal could be the first of many bold moves to keep Boston in championship contention.