Another former Cubs player is now helping run a contender behind the scenes
Earlier this spring, former Chicago Cubs starting pitcher Kyle Hendricks accepted a role with the Detroit Tigers as a special assistant focused on pitching development. The move reunited Hendricks with former Cubs executives Scott Harris and Jeff Greenberg, though it was still disappointing for many fans to see the longtime Cub take on that type of role outside of the organization.
Now, shortly after that move, history appears to be repeating itself as former Cubs outfielder Jason Heyward is reportedly joining the Los Angeles Dodgers organization as a special assistant. Maddie Lee was first to report the news, though Heyward’s exact role or area of focus has not yet been announced.
While Heyward’s tenure with the Cubs was often criticized because of his offensive regression after signing a massive contract, many fans still have a soft spot for him. He remained an elite defender throughout much of his time in Chicago and, of course, was a key part of the club’s 2016 World Series championship team.
Interestingly, Jesse Rogers of ESPN revealed that the Cubs did speak with both Hendricks and Heyward about returning to the organization in off-field roles. However, both ultimately chose to join other organizations, each of which is arguably positioned as a contender in its respective division.
Former Chicago Cubs players Kyle Hendrick and Jason Heyward are now working behind the scenes for 2026 contenders
Hendricks landed in Detroit in a strong overall situation, joining a team that has reached back-to-back ALDS appearances. While Detroit has been hit hard by the loss of ace Tarik Skubal for the next few months, they remain in a relatively weak AL Central, keeping the door wide open for a division push.
On the other hand, the Dodgers remain a powerhouse despite some recent struggles and currently not sitting atop the NL West. Even so, they are still widely expected to be firmly in the mix and contending deep into October.
For the Cubs, the broader takeaway isn’t simply seeing former players land roles with other organization, it’s the growing trend of familiar faces finding opportunities elsewhere rather than returning to Chicago, even with the club currently leading its division and positioned as a contender this season as well.
While these decisions are shaped by a variety of factors, it underscores a simple reality: as memorable as the Cubs’ recent era was, including a championship run, that legacy doesn’t necessarily translate into automatic post-playing reunions once careers come to an end.
The post Another former Cubs player is now helping run a contender behind the scenes appeared first on ChiCitySports.
Source: https://www.chicitysports.com/former-chicago-cubs-outfielder-jason-heyward-special-assistant-los-angeles-dodgers/
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