The Three Best Jason Heyward Moments and What He Meant to the Cubs Organization

Today is Jason Heyward’s 33rd birthday.

There was always a chance, given his complicated swing and the natural vagaries of aging, that he would be on his way out the door by now, after signing an eight-year deal with the Cubs before the 2016 season. You could have predicted it back then. What you might not have predicted is how quickly that descent would begin. It was more or less immediate. Many, many years before his 33rd birthday.

The timing is a little unfortunate, of course, because Heyward is celebrating his birthday knowing that he’ll no longer play for the Cubs, as announced by team president Jed Hoyer yesterday.

Even as things went so poorly, I don’t think it would be fair to say that Heyward did not bring with him many positive things in his nearly seven years in the organization.

“Great teammate,” Hoyer said when asked to assess Heyward’s legacy, per The Athletic. “Someone who — even when he was struggling — tried his absolute hardest every day, every offseason. That’s kind of what I’ll remember. He certainly had his good moments here, but he had a lot of struggles as well. When he had those struggles, he never blamed anyone. He never stopped working. He was always a guy who showed up in the best shape coming into every season. He was always a guy who was in the cages trying to get better.

“From my perspective, he never stopped working. He never stopped trying to earn his contract. He never stopped trying to be better. I think that says a lot. He was, in a lot of ways, an emotional leader of a group of players that broke the curse here and provided fans memories for a lifetime. He should be remembered that way as well.”

There’s only so much “value” in the hard work when the production isn’t there to match, but it certainly isn’t zero. Some players, having secured their one big contract, might have changed their work habits after things started to sour. Heyward, for his part, just kept grinding away to be the best he could still be, and kept leading in the clubhouse.

On that, from Ian Happ in the same Athletic article:

“He’s generous with everything, taking guys out on his boat and paying for team dinners, but also his wealth of knowledge about the game,” Happ said. “Regardless of what he’s doing personally, he’s steady in who he is coming to the field every day. That presence is super important. He kind of epitomizes what it means to be a professional in this game. It’s a lot easier to do that when things are going right. It’s a lot harder to do when things are going wrong. And he’s never wavered.”

Bonus? We’ll never know for sure just how valuable that Game 7 locker room speech was, but we can always tell ourselves it was critical.

There won’t be many unkind words shared about Heyward in the coming days, and whenever his farewell moment is at Wrigley Field. He was everything you’d want in a veteran, big-time signing … except for the results on the field. That’s the main thing. Don’t get me wrong. But the rest of the stuff is why it’s so hard to be dancing on the guy’s grave today, even as I am VERY CERTAIN this is the right move.

Which is not to say Heyward didn’t have some great moments on the field. I wanted to share three of my favorites, which are probably three of your favorites, too. Again, this is on-field stuff, otherwise The Speech would be in here somewhere. Obviously.

There’s no bad time to re-live these moments. No particular order.

There was the time Heyward put Josh Hader’s head on a swivel in a comeback victory in Milwaukee during the pandemic season:

Hader against Heyward with the game on the line … just about the last situation you’d expect to play out as it did. And for fun, Ildemaro Vargas followed with a homer of his own.

There was the time Jason Heyward scored the winning run in that WILD comeback win against the Mariners, with Jon Lester dropping down the walk-off bunt:

And there was the walk-off grand slam against the Phillies. Just one of the most unbelievable and awesome regular season moments in recent memory:

written by

Brett Taylor is the Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and on LinkedIn here. Brett is also the founder of Bleacher Nation, which opened up shop in 2008 as an independent blog about the Chicago Cubs. Later growing to incorporate coverage of other Chicago sports, Bleacher Nation is now one of the largest regional sports blogs on the web.

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