Former Dodgers Outfielder Joins Team in New Role

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. I think that will help me along the way. But at the same time, I think it’s important to learn scouting, how to evaluate players, learn the (research and development) and analytics terminology."

If Heyward ultimately lands an executive role, he'll join several recently retired players along that path. The San Francisco Giants (Buster Posey), Boston Red Sox (Craig Breslow), Seattle Mariners (Jerry Dipoto) and White Sox (Chris Getz) are all led by former players, most of whom played against Heyward from 2010-25.

“In my mind, it would be cool to be a GM, maybe a president one day,” Heyward said, via The Athletic. “Who knows? But it is nice to have an opportunity to learn from what I think is the best.”

Heyward announced his retirement in an Instagram post on March 27. He won five Gold Glove Awards, made an All-Star team and collected National League MVP votes in three seasons.

Heyward finished his career with a slash line of .255/.336/.408 with the Atlanta Braves, St. Louis Cardinals, Cubs, Dodgers, Houston Astros and San Diego Padres.

Jason Heyward gave the most important speech in Cubs history during the Game 7 rain delay in 2016

Respect to a legend pic.twitter.com/jrKRXyBlc5
— Onyx (@OnyxOdds) March 27, 2026

In 2016, Heyward helped the Cubs win a historic championship. His inspirational clubhouse pep talk during a rain delay in Game 7 is widely credited with helping the team score two runs in the 10th inning against the then-Cleveland Indians, and deliver the first World Series title to Chicago's North Side since 1908.

It's a skill that would logically translate to player development while the Dodgers help Heyward round out his baseball operations skill set.

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