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.

more cubs news

MLBits: Red-Hot Rockies, Sticky Stuff Suspension, Salvy’s Patience Paying Off, More

The longest active winning streak in baseball belongs to ... the Rockies. More on the red-hot Rox and more in today's MLB Notes. The Red-Hot Rockies? A little over a week ago, the Rockies were 8-28. Since then, they've won...

The Cubs Are Coming Home to Face the Pirates

Cubs vs Pirates — There's going to be a little deja vu here for the next week, as the Cubs play seven straight games against the Pirates and Braves after just wrapping up six games against ... the Pirates and...

Cubs Farm Report | May 16, 2024: Brennan Davis Goes Yard in Iowa Loss

Brennan Davis' fifth home run of the season was not enough for the Iowa Cubs on Wednesday as they fell to the Syracuse Mets in a rain-shortened affair. That and more in today's Cubs Farm Report. Cubs Farm Report |...

Javier Assad is the Definition of Pitchability

Like his rotation-mate Shota Imanaga, Javier Assad has reached the point where, after every single start, you want to say the same thing: wow, that was awesome, this guy is good. It gets a little stale, in an extremely desirable...

Joe Buck is Returning to the Booth to Call a Cubs-Cardinals Game

I know that Joe Buck is a polarizing broadcaster. Some people love him. Some people hate him. I also know that he seems to have gone through phases in his career where there were stretches I thought he was mutably...

Pete Crow-Armstrong Put on a Show, and Continues to Make a Strong Case for Continued Playing Time

Pete Crow-Armstrong put on a show last night, which I mean in the most literal sense. It was more like a performance than a baseball game. Bases-loaded HBP while showing bunt? OK, sure. Running easily to first on a dropped...

Northwestern Returns to Wrigley Field TWICE This Fall

Northwestern will be making a return to Wrigley Field not just once this season, but twice! Due to the construction of their brand new football stadium, the Cats will be playing five of their seven home games at its temporary...

Impressive Fill-In Guys, Bullpen Health, Roberts, Javy, and Other Cubs Bullets

The Cubs come back home from the Pittsburgh-Atlanta road trip having split it 3-3, and I gotta say, that's a pretty solid outcome when (1) you're facing Jones and Skenes, (2) you're playing three in Atlanta where they'd lost just...

Brennen Davis Homered Again, Back-to-Back with B.J. Murray Jr. (Whom We Should Discuss)

Just about as soon as I could talk about how Brennen Davis had homered for the third time in four games, he homered AGAIN, making it four times in five games. And this time, just for fun, B.J. Murray Jr....

Wake Up and Watch the Cubs Beat the Braves to Salvage the Series

The Chicago Cubs' bats finally came alive last night in Atlanta, albeit with a little bit of help from Braves starting pitcher Charlie Morton. On the other side, Javier Assad was brilliant once again. Good win. Needed win. Enjoy the...

Latest News

New England Patriots Schedule: Dates and Times for All 17 Games, Strength of Schedule, Record Prediction

The New England Patriots are coming off their worst season in over three decades and have officially turned the page on the Belichick-Brady era by hiring Jerod Mayo as their new head coach. They’ve also hit the reset button at...

San Francisco 49ers Schedule: Dates and Times for All 17 Games, Strength of Schedule, Record Prediction

Brock Purdy led the San Francisco 49ers to an NFC Championship and their second Super Bowl appearance in the last five years in 2023. Will they pick up where they left off and continue to dominate the NFC this season?...

Ope! The Bears Also Announced Their 2024 Preseason Schedule

ESPN's Monday Night Football team will call the first game of the Caleb Williams Era when the Chicago Bears play the Houston Texans in the Pro Football Hall of Fame Game. This will mark the first time the Hall of...

The Cubs Are Coming Home to Face the Pirates

Cubs vs Pirates — There's going to be a little deja vu here for the next week, as the Cubs play seven straight games against the Pirates and Braves after just wrapping up six games against ... the Pirates and...

Dodgers vs. Reds Prediction: Expert Picks, Odds, Stats & Best Bets – Thursday, May 16, 2024

The Los Angeles Dodgers (29-16) host the Cincinnati Reds (18-25) on Thursday to begin a four-game series, with the first pitch at 10:10 PM ET from Dodger Stadium. The Dodgers are listed as -329 favorites, while the underdog Reds have...

Anthony Edwards Player Props: Three-Pointer Props and Odds vs. the Nuggets – Conference Semifinals Game 6, Thursday, May 16, 2024

To beat his 3-point prop, Anthony Edwards must make three from beyond the arc on Thursday, when his Minnesota Timberwolves meet the Denver Nuggets in Game 6 of the second round of the NBA playoffs, tipping off at 8:30 PM...

Nikola Jokic Player Props: Three-Pointer Props and Odds vs. the Timberwolves – Conference Semifinals Game 6, Thursday, May 16, 2024

At 8:30 PM ET on Thursday, in Game 6 of the second round of the NBA playoffs, it'll be the Denver Nuggets against the Minnesota Timberwolves, with Nikola Jokic needing two treys to beat his 3-pointer prop.Nikola Jokic's Three-Pointer Prop...

Michael Porter Jr. Player Props: Three-Pointer Props and Odds vs. the Timberwolves – Conference Semifinals Game 6, Thursday, May 16, 2024

To beat his 3-point prop, Michael Porter Jr. needs to make three from downtown on Thursday, when his Denver Nuggets meet the Minnesota Timberwolves in Game 6 of the second round of the NBA playoffs, beginning at 8:30 PM ET.Michael...

Jamal Murray Player Props: Three-Pointer Props and Odds vs. the Timberwolves – Conference Semifinals Game 6, Thursday, May 16, 2024

The Denver Nuggets meet the Minnesota Timberwolves at 8:30 PM ET on Thursday, in Game 6 of the second round of the NBA playoffs, and one of the 3-pointer over/unders available for this matchup requires two triples from Jamal Murray.Jamal...

Karl-Anthony Towns Player Props: Three-Pointer Props and Odds vs. the Nuggets – Conference Semifinals Game 6, Thursday, May 16, 2024

At 8:30 PM ET on Thursday, in Game 6 of the second round of the NBA playoffs, it'll be the Minnesota Timberwolves against the Denver Nuggets, with Karl-Anthony Towns needing three trifectas to beat his 3-pointer over/under.Karl-Anthony Towns' Three-Pointer Prop...

more cubs news