Analysis: Boston Celtics Trade Anfernee Simons to Chicago for Nikola Vucevic, Pick (Report)

The Celtics have decided to rebalance their roster and move Simons to Chicago for Nikola Vucevic. The deal will also result in significant tax savings.

Jan 23, 2026; Brooklyn, New York, USA; Boston Celtics guard Anfernee Simons (4) brings the ball up court against Brooklyn Nets guard Nolan Traore (88) during the first quarter at Barclays Center. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

According to ESPN, the Boston Celtics are trading Anfernee Simons to the Chicago Bulls for Nikola Vucevic and a second-round pick. 

The trade comes as a bit of a surprise considering past rumors that the Celtics rejected offers for Vucevic and Simons’ great recent stretch of play. In the end, the Celtics wanted to rebalance their lineup and help their big-man depth. 

Vucevic is 35, and is averaging 16.9 points per game on 57% shooting on two pointers and 37.6% shooting on threes. His rebounding is down a little bit this year, but he will help shore up Boston’s defensive rebounding, which has been better recently but still ranks in the bottom third of the league. 

His ability to stretch the floor and make plays for his teammates might be what helps Boston the most. He will presumably move into the starting lineup, and his ability to pick-and-pop will open up driving lanes for Jaylen Brown, Derrick White, and Payton Pritchard. The Celtics can also run offense through him at the top of the key and on short rolls and he will do a good job finding openings. 

There's an added bonus of a financial savings. As of this moment, it saves Boston six million dollars in actual salary, but it drops the tax bill from $39.5 million to $17.7 million. 

The move also gets them under the first apron, which removes trade and buyout restrictions. They have a little more than $2 million in room to get to the first apron now, so they are free to do something like pull off a sign-and-trade if one presents itself before the deadline. Acquiring a player via sign-and-trade triggers a hard cap at the first apron.

Another element to this trade is the creation of a $27.7 million traded player exception because the Celtics are using the TPE created by the Kristaps Porzingis trade to acquire Vucevic. This new exception can be used to trade for someone this summer, even if Vucevic walks or re-signs for less money. It can be a valuable tool to build out the roster even further, especially if big-name trades are pushed to the offseason.

This feels like more of a win-now move, which raises questions about Jayson Tatum’s potential return. If Tatum is coming back soon, there is less of a need for Simons, and more of a need to create room for him with a big who can get out of the way. Tatum has expressed some hesitancy about his return, but he is still expected to return when healthy.

The Celtics will also have the same option they had with Simons, which is signing Vucevic to a lesser deal when this one expires this summer. In essence, Vucevic can become a version of Al Horford as an aging stretch big who can make plays for others.