A Cubs Fan Processes Jason Heyward’s Tenure

Jason Heyward's time in Chicago is at its end. How should we feel?

And you may ask yourself, “How do I work this?”

Funny thing, time. The first several years of Jason Heyward’s career didn’t exactly lend himself to becoming the stuff of legend in Chicago. For good reasons, anyway. His Major League debut was against the Cubs. He deposited a Carlos Zambrano pitch 430+ feet into the seats in Atlanta before scorching a single off Justin Berg later in that game. He was 2-for-5, and I don’t remember what the score was other than it being intensely lopsided. And I know Jason Heyward was very good. Later on in the timeline, he’s a St. Louis Cardinal on a squad that won the National League Central in 2015.

These are largely two insignificant details that I just happen to find mildly fun and barely ironic. Heyward blasted the Cubs in his debut, ended up front-and-center against the Cubs in St. Louis, and then signed a massive contract with those same Cubs. At the end of the 2022 season, the Chicago Cubs will release Jason Heyward. The team announced at the beginning of August that Heyward would not return this year, or ever.

With one year left on his contract, production continuing to wane, and the team boasting an abundance of talented, young outfielders in the system, it’s not as if it came as any sort of surprise. Nonetheless, I have still found myself spending the last several weeks struggling with how I would approach this. It wasn’t so much an instance of writer’s block, either. Jason Heyward’s tenure in Chicago was complicated. But also, it wasn’t? And here’s where I start to very publicly process how I feel about Jason Heyward.

And you may ask yourself, “Where is that large automobile?”

Heyward was an extremely good player prior to signing with the Cubs. In Atlanta, he had a pair of seasons with an fWAR over 4.5 and another one over five. In St. Louis, he touched a career-high at 5.6. When news of the signing broke, I was teaching American Lit (you can probably land specifically what I was teaching within three guesses). I stopped class to write the projected lineup on the board. I was very good at my job. It was an exciting thing, to be sure. The team had already signed Jon Lester the previous winter and that optimistic buzz was still very much alive after a deeper-than-expected postseason run even after it was destroyed by the extremely likable Daniel Murphy.

And we know how the rest worked out. The Cubs did, in fact, win the World Series in 2016. They broke the primary timeline and are likely directly responsible for the mangled society in which we find ourselves. Much of that is probably Heyward’s fault, too. He gave the famous speech during the rain delay which allowed the Cubs to rally back after Rajai Davis did his thing, catapulting them to a tenth-inning rally that ended a century-plus of misery.

And you may tell yourself, “This is not my beautiful house”

Barely five years later and Cubs fans have been jettisoned back into a familiar emotional state. The departures of Anthony Rizzo, Kris Bryant, Kyle Schwarber, and Javier Báez (among others) have largely landed the fanbase in such territory. Interestingly, Heyward’s imminent departure hasn’t been met with quite the same level of despair. And I think that is part of what makes his legacy in Chicago so complicated.

The deal that Jason Heyward signed with the Cubs was for eight years and $184 million. Heyward’s best season by way of fWAR came in 2018, at 2.7. In terms of wRC+, he had two seasons where he was exactly average, at 100 (2018 & 2019). His best offensive season came with a wRC+ of 131 across 50 games…in 2020. He wasn’t a good offensive player during his tenure. His swing was a mess. The rollover grounders to second base seemed to play on a loop with each plate appearance. His last full season was probably the worst of his career. But, somehow, none of that matters.

It’s not as if the Cubs were some model organization in terms of performance post-2016 or if Heyward was the singular catalyst holding them back from contention. They all had their individual moments amidst a sea of mediocrity after the title. Heyward’s contract put him under the microscope. That’s just the way it works. I’ll remember Jason Heyward’s time in Chicago for the Game 7 speech in rainy Cleveland. The walk-off grand slam against the Phillies in 2018. The three-run job off of Josh Hader in 2020. Most importantly, though, I’ll remember how much Jason Heyward loved playing for the Chicago Cubs.

And you may tell yourself, “This is not my beautiful wife”

Maybe I’m a sucker for sentiment. I’m for sure a sucker for glove-first Major Leaguers who are only occasionally good at the plate. I can’t look at the seven years that Heyward will have spent as a Cub as better than the rest of the core whose departure leveled an entire fanbase over 48 hours. But the nostalgia meter is definitely going to feel a bit emptier once he’s gone. And as someone who clings to nostalgia as a drug of choice, there will be a withdrawal. Thank goodness Jed Hoyer and Co. are here to build the “next great Cubs team.”

As fans, we aren’t privy to the inner workings of the clubhouse. So there’s something to be said for a guy who very obviously loved what he was doing, where he was doing it, and who he was doing it with. I don’t have any doubts in my mind that Heyward will end up back in some sort of capacity and the organization will be the better for it. For now, we’ll see what the future offers. He could grab a minor league deal somewhere, with hopes of latching onto a young club with immediate postseason aspirations that could use the leadership boost and a late-inning defensive outfielder. Maybe he doesn’t. But his absence, just as the much-more-discussed-and-just-as-imminent absence of Willson Contreras, will be felt by all.

Same as it ever was, same as it ever was

We can only hope this alleged “next great Cubs team” carries someone with so much emotional weight, both for the city and those around him.

Author’s Note: Did the Talking Heads subheaders work, logically? Probably not. But I bet that instrumental is stuck in your head while you’re ruminating on a long-tenured player seeing his final days after seven years with the same organization. Yeah, enjoy that sadness. 


Photo by Dan Sanger/Icon Sportswire |  Illustration by Cody Rogers (@CodyRogers10)

Randy Holt

Randy Holt is a staff writer for Pitcher List & a depth charts analyst for Baseball Prospectus. He's a self-identified Cubs fan who has become more agnostic, instead obsessing about quality defensive baseball wherever he can find it. Randy has a sport management degree from the University of Florida, as well as degrees from Embry-Riddle & Arizona State. When not wasting away on the husk of Twitter/X, Randy is a high school English teacher & a baseball and golf coach.

One response to “A Cubs Fan Processes Jason Heyward’s Tenure”

  1. Juan says:

    Love the song reference in the titles

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