First Hendricks, Now Heyward – Cubs Fail to Add Another 2016 Legend to Front Office

The Chicago Cubs may want appoint a new alumni club leader.

For the second time this season, the organization has watched a recent franchise legend accept a front office role with another franchise. Jason Heyward has accepted a position inside the Los Angeles Dodgers front office. The former Cubs outfielder will work as a special assistant and help out with the team's affiliates, per Alden González. Heyward played for the Dodgers during the 2023 season and a chunk of the 2024 campaign.

The Athletic shared more insight on Heyward's new role, which the 36-year-old is seemingly hoping will be his first step in a long secondary career. To be sure, a "senior advisor" role can certainly be viewed as a largely symbolic position, but Heyward has made clear that he intends to use this as an opportunity to learn the front office ropes.

Dodgers manager Dave Roberts even spoke to this point, telling The Athletic's Fabian Ardaya that this will give Heyward a good look at the other side of the game. There is no question that the 16-year veteran already mastered the art of clubhouse leadership.

Speaking of which ...

Cubs Watch Another Former Leader Go Elsewhere

Aug 29, 2025; Los Angeles, California, USA; Free agent Jason Heyward looks on before the game between the Arizona Diamondbacks and the Los Angeles Dodgers at Dodger Stadium. Mandatory Credit: Kirby Lee-Imagn Images | Kirby Lee-Imagn Images

Jason Heyward isn't just any former Cub. He isn't even just a former member of their 2016 World Series squad. The right fielder was responsible for the iconic locker room speech during the Game 7 rain delay. Vibes were reportedly low as the young group blew their lead and faced a scary trip into extra innings on the road. Heyward – a calm and collected leader – was the one to gather the troops and lift their spirits.

Of course, Heyward also went on to spend seven years in Chicago, which marked the most with any one team in his career. Did J-Hey fully live up to the hype that came with his lofty contract? No, and this undoubtedly led some fans to have mixed feelings about the five-time Gold Glove winner. But he was still a valuable and professional constant for the Cubs for over a decade. If anyone ever said in the past that he was destined for a front office role, many would have assumed the Cubs would be first in line.

Nevertheless, Heyward chose to follow a similar path to Kyle Hendricks and has teamed up with a heated NL rival in the process. The team's Game 7 starting pitcher chose to ink a deal to join the Detroit Tigers front office earlier this season. A couple of the top decision-makers in Detroit stem from the Cubs' braintrust.

Jesse Rogers of ESPN did report that the Cubs spoke with both Hendricks and Heyward about potential roles. In other words, it's not as if they were completely against the idea of welcoming either back into the organization. However, this only makes it feel slightly more alarming that neither decided to join the fold. What about the fit wasn't right? Were the Cubs not serious enough about welcoming either back?

If one thing is for sure, both Heyward and Hendricks feel like former players who could turn into quite valuable front office minds. They were also clearly willing to start from the ground up, meaning there was likely no expectation of special treatment with the Cubs. Is it possible they wanted to separate themselves from all the history and fanfare in Chicago? Sure, but one has to imagine the Cubs could have secured one or the other if they really wanted to.

At the end of the day, it's not as if this news is going to make or break the Cubs' system. There is also a world where the franchise links back up with either down the road, as they continue to climb the front office ladder. However, there is no question that it's an odd feeling to see another member of the World Series squad begin the next step of their career elsewhere. If Anthony Rizzo becomes a Yankees scout ... I'll scream!

Add us as a preferred source on Google