The Chicago Bulls have a decision to make on their trade deadline acquisition, Anfernee Simons.
As the standout guard’s contract expires this week, Simons will be free to speak with teams in NBA free agency, which begins on June 30.
According to The Stein Line’s Jake Fischer, Chicago is thinking about bringing Simons back for another run after his short stint with the team. However, there are threats in the mix.
Chicago Bulls Get Warning About Celtics Before NBA Free Agency
GettyMIAMI, FLORIDA – JANUARY 15: Jaylen Brown #7 and Anfernee Simons #4 of the Boston Celtics celebrate during the fourth quarter of the game against the Miami Heat at Kaseya Center on January 15, 2026 in Miami, Florida. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement (Photo by Megan Briggs/Getty Images)
“Sources say Chicago is also giving consideration to bringing back scoring guard Anfernee Simons, who is expected to draw external interest from teams such as Golden State and Boston,” Fischer wrote early on Tuesday morning.
Simons joined the Bulls after a multi-month run with the Celtics. He was a returning piece in the Nikola Vucevic trade.
GettyBOSTON, MASSACHUSETTS – NOVEMBER 23: Anfernee Simons #4 of the Boston Celtics looks on during the second half at TD Garden on November 23, 2025 in Boston, Massachusetts. The Celtics defeat the Magic 138-129. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Maddie Meyer/Getty Images)
While the Celtics enjoyed Simons’ presence, they felt they needed a veteran center to patch up the concerns in the frontcourt. After Simons left, the organization sent signals across the league, making it clear that Simons would be a tagret in free agency.
It turns out that’s truly the case.
Anfernee Simons’ NBA Career
GettyNEW YORK, NEW YORK – FEBRUARY 09: Anfernee Simons #22 of the Chicago Bulls warms up prior to the game against the Brooklyn Nets at Barclays Center on February 09, 2026 in New York City. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Evan Bernstein/Getty Images)
In 2018, Simons entered the NBA Draft.
At the time, he was selected in the first round, 24th overall by the Portland Trail Blazers.
Simons didn’t have an immediate role, but he averaged 20.7 minutes off the bench during his second season in Portland.
GettyNEW YORK, NEW YORK – FEBRUARY 09: Nolan Traore #88 of the Brooklyn Nets handles the ball as Anfernee Simons #22 of the Chicago Bulls defends in the second half at Barclays Center on February 09, 2026 in New York City. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Evan Bernstein/Getty Images)
Eventually, Simons became a full-time starter and earned himself a notable contract extension with the team.
Heading into the final season of his four-year, $100 million contract, Simons was traded to the Celtics.
After Simons moved to the Bulls, he only had a chance to play in six games due to an injury. He averaged 28.4 minutes on the court. Simons produced 15.2 points per game, while shooting 32.0% from three.