Another beloved teammate and leader on the 2016 Chicago Cubs World Series team is joining an MLB front office outside of Chicago.
Jason Heyward is joining the Dodgers front office as a special assistant:
Jason Heyward is joining the Dodgers front office as a special assistant. @maddie_m_lee was on it. Not much of a surprise given how beloved he was in his time in Los Angeles. Dave Roberts said he will be going around to different affiliates to observe. He’s here today.
— Fabian Ardaya (@FabianArdaya) May 13, 2026Jason Heyward was considered an elite mentor during his time as a Dodger player. Now the Dodgers will use those skills and others to impact the club as a special assistant. Story: t.co/dSoed8t9xH
— Dodger Insider (@DodgerInsider) May 14, 2026Jason Heyward has joined the Dodgers as a special assistant, with high aspirations for a future in a front office: “In my mind, it would be cool to be a GM, maybe a president one day. Who knows? But it’s nice to have an opportunity.” t.co/IskbvOjyNm
— Fabian Ardaya (@FabianArdaya) May 14, 2026Hey, good for Jason Heyward. He’s a natural leader and was always as well-regarded as any teammate in recent memory. The Dodgers are fortunate to have his eyes and mind working with their young talent.
Like Kyle Hendricks, there were apparently discussions between the Cubs and Jason Heyward about a post-playing role, but he elected to go elsewhere:
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. t.co/2izqiEla0E
— Jesse Rogers (@JesseRogersESPN) May 13, 2026Interestingly, the reporting on Hendricks and the Cubs suggested that he was excited to get a chance to work with developing Tigers prospects, and it sounds like the same is true for Heyward on the positional side. Were the Cubs less open to that in their cases? Or maybe less inclined to provide immediate leadership roles? Were other relationships a factor (we know Hendricks is close with much of the Tigers’ front office, which had come over from the Cubs; and obviously Heyward spent some of his later years with the Dodgers)? Combination of things?
I don’t see any reason to be TOO upset about these things, even if it’s disappointing as a fan. I wish these guys well, and you never know when their paths might cross again down the road with the Cubs after getting some experience elsewhere.
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