Jason Heyward is following a well-trodden path to what he hopes is a successful second act in baseball. Heyward, 36, is the newest special assistant in the Los Angeles Dodgers' baseball operations department. The new job comes less than two months after Heyward announced his retirement after 16 MLB seasons — including two (2023-24) in Los Angeles. According to Jesse Rogers of ESPN, Heyward also talked to the Chicago Cubs and Chicago White Sox about a role in their organizations before signing on with the Dodgers. The Cubs spoke with Jason Heyward and Kyle Hendricks about re-joining the organization but they both went elsewhere. The White Sox also talked with Heyward. https://t.co/2izqiEla0E — Jesse Rogers (@JesseRogersESPN) May 13, 2026 “I asked for an opportunity,” Heyward said, via Dodger Insider . “I had a goal of potentially being in the front office. But I understand there’s a lot to learn on this side of the game. It’s great to be a player, great to have that experience.…