LOS ANGELES, CA – JUNE 24: Jason Heyward #22 of the Chicago Cubs looks on during the game between the Chicago Cubs and the Los Angeles Dodgers at Dodgers Stadium on Thursday, June 24, 2021 in Los Angeles, California. (Photo by Daniel Shirey/MLB Photos via Getty Images)
MLB Photos via Getty Images
The Los Angeles Dodgers are enjoying the perspective and knowledge of a revered World Series champion in a surprising new role, though he evidently first tried to bring that perspective to another former team.
After a lengthy and decorated career with several big market franchises, former Gold Glove outfielder Jason Heyward ended his playing career and almost immediately joined the Dodgers in an advisory role.
“The 36-year-old five-time Gold Glove outfielder has taken a job with the Los Angeles Dodgers, one of the six teams he played for during his 16-year MLB career,” the Associated Press reported in May. “He’s best known for his time with the Chicago Cubs, winning the World Series in 2016.”
Heyward’s new role as a special assistant gives him an opportunity to apply lessons from a career that included major individual and team accomplishments. And Cubs fans might be wondering why those lessons couldn’t benefit their own favorite team’s operations.
Chicago Cubs Were Jason Heyward First Choice For Post-Playing Career
Heyward’s connection to Chicago remains particularly significant.
The Cubs signed him to an eight-year, $184 million contract before the 2016 season, making him one of the most prominent additions to a team attempting to end its historic championship drought.
And Heyward quickly became an important part of the Cubs’ championship story. During the 2016 World Series, he famously led a players-only meeting during a rain delay before Chicago eventually defeated Cleveland in an unforgettable Game 7.
And that tenure influenced Heyward’s first move after he decided to start a new career after his playing days ended.
“He said he reached out to the Cubs first about a non-playing role,” the Los Angeles Times’ Maddie Lee reported. “In many ways, it came down to timing.”
Though Heyward didn’t detail how the Cubs responded to his initial interest, the Dodgers ultimately became the organization that provided Heyward with his next opportunity following some meetings with Andrew Friedman and Dave Roberts, who evidently jumped at the chance to hire him more quickly than the Cubs.
Los Angeles Dodgers Gain Veteran Perspective After Chicago Cubs Outreach
Heyward spent the 2024 season with the Houston Astros and followed that with a season with the San Diego Padres. Entering the most recent offseason, he remained prepared to play if the right opportunity emerged while simultaneously preparing himself for life after baseball.
“Heyward finished 2024 with the (Houston) Astros and spent the next season with the Padres,” Lee added. “He trained this past offseason to be ready for spring training if a team gave him an offer. But in the final weeks, he also started laying groundwork for a post-playing career in case the phone never rang.”
Now, a unique combination of recent playing experience and a championship pedigree could make Heyward particularly useful to the Dodgers.
He has experienced the pressure that comes with a massive contract, the demands of playing for a championship contender and the challenges of adjusting when a player’s career does not unfold exactly as expected. But for whatever reason, the Cubs didn’t take him up on his initial interest.