Astandout veteran for the Chicago Bulls could be on the move after joining the team late in the 2025-2026 NBA season.
Anfernee Simons is set to hit the free agency market and should be viewed as a potential flight risk out of Illinois.
Grant Hughes of Bleacher Report highlighted top trade and free agency targets for each NBA team. When landing on the Orlando Magic, the writer suggested that Simons could be the second-best option behind Ryan Rollins.
Orlando Magic Urged To Snatch Chicago Bulls Player in NBA Free Agency
GettyNEW YORK, NEW YORK – FEBRUARY 09: Ben Saraf #77 of the Brooklyn Nets handles the ball as Anfernee Simons #22 of the Chicago Bulls defends in the first 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)
“Simons won’t be available at the minimum, but maybe the Magic will shuffle up the roster enough to use one of the mid-level exceptions,” Hughes explained.
“Failing that, [Tim] Hardaway could be a solid trade option as long as Orlando believes he can match the 40.7 percent he shot from deep last year.”
Simons’ value heading into free agency is all over the place.
Some NBA insiders and analysts have suggested that Simons could take a short-term offer with a contender in order to help drive his value back up before another free agency run.
But being in the league since 2018, Simons has done enough in his career to ask for another notable multi-year contract.
Anfernee Simons’ NBA Career
GettyCHICAGO, ILLINOIS – FEBRUARY 19: Brandon Ingram #3 of the Toronto Raptors drives to the basket as Anfernee Simons #22 of the Chicago Bulls defends during the first half at the United Center on February 19, 2026 in Chicago, Illinois. 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 Daniel Bartel/Getty Images)
Simons held out of college and entered the NBA Draft in 2018. He was selected in the first round with the 24th overall pick.
Simons started his career with the Portland Trail Blazers. Over seven seasons with the Blazers, Simons appeared in 389 games. He produced averages of 15.0 points, 3.3 assists, and 2.2 rebounds.
Back in July 2025, Simons was traded to the Boston Celtics.
In 49 games with the Celtics, Simons came off the bench for 24.5 minutes per game. The veteran guard shot 32.0% from three. He averaged 15.2 points, 2.8 rebounds, and 3.0 assists per game.
After getting traded to the Bulls in 2025-2026, Simons appeared in just six games before suffering an injury. He produced 15.2 points per game, while hitting on 43.8% of his shots during the short stretch.
The Bulls have space to spend and keep Simons on board. The 27-year-old could be looking for a competitive situation, which is something he could get in Orlando. The Bulls’ revamped front office has yet to reveal its hand on the Simons front.