Jason Heyward Admits He Approached the Cubs First Before Joining Dodgers in Advisory Role

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 benefiting from the insight and experience of a respected World Series champion in an unexpected new capacity, though he initially attempted to bring that expertise to a different former club.

Following a long and accomplished career with several major market teams, former Gold Glove outfielder Jason Heyward concluded his playing days and promptly transitioned into an advisory position with the Dodgers.

According to the Associated Press in May, “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. He’s best known for his time with the Chicago Cubs, winning the World Series in 2016.”

Heyward’s new position as a special assistant offers him a platform to share lessons drawn from a career marked by significant individual milestones and team triumphs. Cubs supporters may be curious about why those insights couldn’t have been utilized by their own organization.

Chicago Cubs Were Jason Heyward’s First Choice for Post-Playing Career

Heyward’s ties to Chicago remain notably strong.

The Cubs secured him with an eight-year, $184 million contract ahead of the 2016 season, positioning him as one of the marquee acquisitions for a franchise determined to break its lengthy championship drought.

Heyward rapidly emerged as a pivotal figure in the Cubs’ championship run. During the 2016 World Series, he notably spearheaded a players-only meeting during a rain delay before Chicago ultimately triumphed over Cleveland in a memorable Game 7.

That chapter in Chicago shaped Heyward’s initial step as he began charting a new professional path after retiring as a player.

As reported by the Los Angeles Times’ Maddie Lee, “He said he reached out to the Cubs first about a non-playing role. In many ways, it came down to timing.”

While Heyward did not elaborate on how the Cubs reacted to his inquiry, the Dodgers ultimately became the franchise that offered him his next opportunity. After meeting with Andrew Friedman and Dave Roberts, the Los Angeles front office moved swiftly to bring him on board, outpacing Chicago in the process.

Los Angeles Dodgers Gain Veteran Perspective After Chicago Cubs Outreach

Heyward concluded the 2024 season with the Houston Astros and subsequently spent a year with the San Diego Padres. Heading into the most recent offseason, he remained ready to continue playing if the right opportunity presented itself, while also preparing for a career beyond baseball.

Lee noted, “Heyward finished 2024 with the (Houston) Astros and spent the next season with the Padres. 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 distinctive blend of recent playing experience and a championship résumé could prove especially valuable to the Dodgers.

He has navigated the weight of a substantial contract, the intensity of contending for championships, and the difficulties of adapting when a career does not develop as anticipated. Yet for reasons unspecified, the Cubs did not pursue his initial expression of interest.

Source link