Proposed Trade Sees Celtics Flip Simons in 2-for-1 Deal

Anfernee Simons joined the Boston Celtics as part of the trade that sent Jrue Holiday to the Portland Trail Blazers. Simons is entering the final year of his contract and will earn $27.6 million.

Boston is marginally in the second luxury tax apron. After moving Holiday and Kristaps Porzingis this summer, along with losing Luke Kornet and potentially Al Horford, it’s unlikely Brad Stevens will want to remain a second-apron team. Therefore, Simons could potentially be re-routed before the season begins.

ClutchPoint’s Bailey Bassett has proposed a trade that would help the Celtics duck under the second luxury tax apron. The trade would also add some additional perimeter shooting. The proposed deal would look like this:

Wizards receive: Anfernee Simons

Celtics receive: Corey Kispert, Richaun Holmes, two second-round picks

“Richaun Holmes is under contract for two more seasons, and Corey Kispert won’t hit the open market until after the 2028-29 season,” Bassett reasoned. “…Both of them could have an impact on the Celtics’ roster upon Tatum’s return. Boston is particularly thin at the center position, so Holmes could have a big role with the team…Kispert would also be an intriguing option because he is one of the best 3-point shooters in the NBA.”

Kispert is entering the first year of a four-year deal and will earn $13.97 million next season. Holmes, 31, is set to earn $13.28 million. The only way this proposed trade can happen is if the Celtics, as a second-apron team, match the outgoing salary with the combined salaries of the two players coming back. Alternatively, the deal could work if it gets them under the second luxury tax apron entirely.

Otherwise, second-apron teams are stuck with strict 1-for-1 salary matching.

Celtics Could Re-Unite With Marcus Smart

According to Jake Weinbach, the Celtics could reunite with Marcus Smart if he’s made available this summer.

“A potential reunion between Marcus Smart and the Celtics would not be off the table,” Weinbach reported via X. “The Wizards, who now carry 17 players on the active roster, are expected to offload key veterans to make room for younger assets and would reportedly prefer to send Smart to a desired location.”

Whether Boston would want to bring back the combative ball-handler would remain to be seen. However, there’s no doubt that he would immediately improve the roster and command a sizeable role in the second unit.

Celtics Trying to Trade Anfernee Simons

According to Brian Windhorst, speaking via his “The Hoops Collective” podcast, Brad Stevens and the Celtics are “actively” looking to trade Simons this summer.

“I have talked to other teams that have said the Celtics are actively trying to trade Anfernee Simons,” Windhorst said. “Whether they can or not is another [thing].”

Simons fits the Celtics’ offensive system perfectly. However, his high-cost contract and limited defensive ability could lead the front office to explore its options. After all, the upcoming season is about developing talent to slot next to Jayson Tatum and Jaylen Brown. Therefore, if Simons isn’t going to be a good fit; flipping him is the best course of action.