Jayson Heyward celebrates with his Dodgers teammates in 2024. Now, he returns in a front office role.

The Los Angeles Dodgers organization is certainly not lacking in World Series Champions. Nearly the entire team, coaching staff, and front office have at least one World Series win from 2025, and most have a ring from 2024 as well. Some have three rings, going back to 2020.

However, it can never hurt to add one more World Series Champion. Especially one who is a fan favorite and was once an All-Star caliber player and gold glove winner.

The player in question is former Dodgers outfielder Jayson Heyward, who is returning to the Los Angeles organization not as a player, but as a special assistant to the front office.

Heyward, 36, last played in the MLB in 2025 with the San Diego Padres. He spent a year and a half in Los Angeles, mostly as a platoon outfielder in 2023 and 2024. He was traded to the Astros in the middle of the 2024 season, and missed out on the World Series celebrations, but Heyward is better known for his time with the Chicago Cubs, where he was a starter for the 2016 World Series-winning team.

He spent his entire career playing for winning organizations, playing for the Braves, Cardinals, Cubs, Dodgers, Astros, and Padres. In fact, Heyward was only part of a losing team three times in his 16-year career (2014 Braves, 2021 Cubs, 2022 Cubs). He played for 13 winning teams and reached the postseason 10 times.

After spending his past 16 years patrolling the outfield for some of the best and most well-run organizations in baseball, Heyward is moving into a new role, working with the Dodgers’ front office.

Heyward’s Ambitions Don’t End As an Assistant

In an interview with the California Post, Heyward revealed that he has larger aspirations that simply being an assistant. Someday, Heyward would like to serve in a permanent front office role.

“I asked for an opportunity to learn,” Heyward told Jack Harris of the California Post. “I have a goal of potentially one day being in the front office.”

Heyward told Harris that in his final years as a player, he began to find himself becoming interested in how ballclub’s are run, and decided he was interesting in eventually moving into a front office job.

Long term, he told Harris that he would find it “amazing” to be a General Manager of an MLB team. For now, however, he’s with the Dodgers to learn.

“Again, I don’t know what that route looks like right now today, coming here without much experience in it,” Heyward said. “But that’s what I’m here to work toward.”

Heyward’s Roller Coaster Career

Heyward had a roller coaster career. At 20 years old, he was an All-Star, and finished runner-up in Rookie of the Year voting with the Braves, accumulating 6.4 bWAR. After a sophomore slump which saw Heyward’s OPS dip by 141 points, and his bWAR slip to just 2.0, he put together a very strong three-year stretch in Atlanta.

From 2012-2014, Heyward slashed .266/.345/.431, with a 113 OPS+ and 14.6 bWAR (averaging nearly 5-WAR per season). He won two gold gloves, and even recieved MVP votes in 2012. Despite this, he was not named an All-Star again with the Braves.

In 2015, Heyward was acquired by the Cardinals, where he had a career-year. He was worth 7.0 bWAR, and set career-highs in hits (160), doubles (33), stolen bases (23), and batting average (.293). He won his third gold glove award, and again earned MVP votes, but once again, was not an All-Star.

At this point, through his first six seasons, Heyward had accumulated 29.9 bWAR and had just one All-Star nod to show for it.

After his strong 2015 season, Heyward joined the Cubs, with whom he would sign a long-term contract. However, Heyward was never the same after joining Chicago. In the final ten years of his career, he averaged 1.2 bWAR per season, and had an 88 OPS+. He did win a World Series in Chicago, and added two more gold glove awards as well, in 2016 and 2017.