Jason Heyward on Life, Business and The State of Race in MLB

Jason Heyward joins En Fuego to discuss Fernando Tatis Jr.’s flair, his business interests outside baseball and the subject felt throughout the nation. He opens up about race and representation in MLB.
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Jason Heyward is deliberate when he speaks, thoughtful and engaging. He’s in the middle of a most remarkable season and he’s dealing with it in that same measured manner that has made him one of the more respected clubhouse leaders in baseball.

“When we first got together initially back in Chicago was just make sure we address all the things going on in everyone's lives right now before we get back to baseball, so we can first focus on that,” Heyward tells En Fuego on Sports Illustrated. “Address it. Talk about it. Get on the same page and then move forward as a group.”

Heyward is speaking to me way back on Aug. 13, which seems like a lifetime ago. If time is a flat circle it moves ever so quickly in a pandemic before doubling back again.

One tragic event after another happens as we all continue to feel the pangs of anxiety due to the constraints of COVID safety precautions.

And while Heyward decided to sit last week in protest of the Jacob Blake shooting, our discussion prior to more recent events is all the more prescient in its context.

My discussion with Heyward was wonderfully expansive. At just 31, he’s baseball wisdom personified.

A Business, Man

Jason Heyward became a professional baseball player at 17.

Think about that. The same age some of us were still discovering what music we were really into or whether we might go away to college a year later, Heyward had the weight and the confidence of a franchise on his shoulders.

Going into college, he had a decision, one that would shape who he was and the path of his career. Education is a big part of who he is, both of his parents went to Dartmouth. His uncle, Kenny Washington, won titles at U.C.L.A. under John Wooden. And it was that school that recruited Heyward heavily.

But his parents instilled in him a confidence in himself, going pro at an early age was really the only choice looking back on it now.

“Having the support of my parents, they always pushed me to earn everything that I have and to set your goals as high as possible,” Heyward tells En Fuego. “They wanted me to be able to make my own decision for myself. They believed in that firmly. But they also believe in education, of course. And once I was able to get into college and sign a letter of intent, they felt, ‘OK, well, he did this part; He did what we asked him to do.’”

His parents understood that his goals, the sacrifices he had made up to that point, were all pointed in one direction, the diamond.

“I came into it young professionally,” Heyward said. “So, starting off it was just like, hey, how do I become an adult, play this game, build a career and become established?”

Working hard and being a clubhouse leader seems to be a good recipe for success. That work ethic has seen Heyward play over a decade, collect five Gold Gloves, an All-Star nod and a championship with the Cubs in 2016.

Read More: Jason Heyward, Santia Deck Headline the First Episode of the En Fuego Podcast

But if the Bigs were calling to that bright-eyed 17-year-old, another chapter is waiting to be written for this athlete.

“Here I am, 31 years old, going on 11 seasons, and you start to start to realize, hey, there are things that I want to use this platform for and take advantage of (from) a business aspect when I'm done playing, because I hear from a lot of guys that are now going through that transition,” Heyward said.

Last Wednesday, Sportico announced Heyward would be the first professional athlete to join Turn2 Equity Partners.

The group that also includes co-chairmen Jarett Sims and Peter Stein along with Astros manager Dusty Baker, former general managers Bobby Evans and Jim Duquette, along with former MLB Advanced Media executive VP Dinn Mann, are not only empowering athletes with the tools to succeed in a media-centric world but also allowing investors to shape and craft the scope of content going forward. Heyward is also heavily involved in his Atlanta-based training facility, DSA Training.

Instead of waiting for the next step, Heyward is carefully preparing for that step with methodical investments he believes in.

“You've got to be ready for what comes next,” He said. “And with Turn2 that was for me, my mindset on getting involved and investing in it and also investing in something that's going to have something to do with my future and something that I can actively be a part of and get acclimated with in this transition phase when it does happen for me.”

Having a player like Heyward resonates profoundly not only for the business acumen he possesses but also for his perspective on subjects outside of baseball.

Being Black in Baseball

African Americans are not flocking to the diamond in the numbers they once did. In 1981, they made up 18.7% of MLB. While the percentage of Latino players in the sport has risen dramatically over the decades, the number of African American players has dwindled to under 8%.

Baseball absolutely has to have better outreach into the Black communities. The Cubs outfielder explained he and his teammates have discussed this very topic.

“There are no baseball fields in certain areas. There are no sports facilities. There are no basketball courts or anything in certain areas,” Heyward said.

Opening Day in 2019 was a telling one in this regard, ballclubs welcomed 68 African-American players to the field out of 882 players, that’s 7.7% of the game.

Besides access, there is a major issue in compensation. A top athlete can go to college and head to the NFL and make serious money. A top-flight baseball player, even one like Heyward, may have to scrap through six levels of the minors before ever seeing the show.

Other sports have more scholarships to go around, making it far more attractive an opportunity. Success in baseball often means a real commitment financially, a commitment some families might not be able to meet.

“In a black community, the biggest influence is going to be NFL; it's going to be NBA. Now with the NFL, there are a lot of scholarships and a lot of opportunities to get into college because there are a lot of numbers,” Heyward explained. “That's leaving a lot of money that has to be spent by a family to send a kid to college to give them an opportunity to go further in (baseball). So, I feel like there's just not a lot of opportunity as other sports.”

And the issue is a stark lack of representation, something that became all the more apparent this past week amid a wave of protests.

Heyward continued, “in a work environment, in the sport of baseball, you don't see a lot of us around.”

Getting that to change is a bigger conversation, one that will take so many things to change before young African Americans pick up a bat and glove in larger numbers. But there is an avenue to be discussed.

“I think maybe that we have to find a way to get that to change or to get it more accessible in college,” Heyward explained. “Regardless of your home situation, we're all taught go to school, get good grades and things happen for you. Well, that's not necessarily the case when it comes to baseball. Right. So then African-Americans not having that opportunity in more situations than not, you know, I just think it's there's a lot of dead ends in it.”

Representation leads to empowerment and making the game far more equitable moving forward.

“In the game of baseball, it's always been you're afraid to speak out on things like that (race). You're afraid to speak on anything but baseball, especially as an African-American.”

A Bright Future 

Heyward is an old school player, grinding out the seasons with class and an arduous dedication to his craft. But that doesn’t mean he is stuck in an old school mentality.

He understands the benefit of embracing change and embracing the sizzle of flashy play coming up through the ranks.

“You talk about (Fernando) Tatis Jr., this new wave of players pimping home runs or showing flair or showing excitement is more accepted now, which I'm honestly a fan of because it's a different era,” Heyward said.

The San Diego Padres’ Tatis Jr. has become something of the face of a new, flashier generation in this sport. A couple of his more recent exploits was hitting a grand slam on a 3-0 count with his team up big and stealing third the following night under similar circumstances.

It’s so remarkably easy to love a guy like Tatis Jr., even though he dares break some of those rules nobody bothered to write down.

“It's kids coming up and bringing excitement,” Heyward said. “When I came into the game in 2010, you pimp a home run, you're going to have a problem. And that's just 2010.”

The game, however, it’s changing. “Before I got here, it was that much worse. So, I just think the game is slowly changing. And talking about the exposure, it wasn't the norm. Now it's becoming more of that. And I think it's there's a good way to balance it. And hopefully, we continue to find that with baseball.”

It certainly sounds like Heyward is all in on the fun, bat flips, pimping home runs and making this game more dynamic visually. Well, pause that thought. Heyward is refreshingly old school in this regard.

You can strut your stuff. Just know you have to get back in that box and face the chin music.

“If you're not on my team then you're not on my team’ that's for your team to handle. But just be ready to handle whatever comes with your actions.”

Dealing with COVID

None of us know what we’re doing at this moment. COVID, self-isolating during a pandemic, it’s kicking all of our butts. I like to think Heyward has a solution though. “My fiancé and I, we got two puppies. We got them during COVID because we needed something to keep the mood light and keep us in a routine.”

It’s simple, but it’s kind of the blueprint these Cubs are using to get through what has to be the most trying season of their respective careers. I’m not saying there are puppies running around the clubhouse, but it’s not a terrible idea. What Chicago is doing is keeping things light when they can.

“It's just one of those vibes where you really got to make the most of this to remember why you started playing this game, because you love it, because you have fun with the camaraderie,” Heyward said.

The Cubs are 20-14. First in their division. They are playing things out, not knowing where the season will go or the direction the country is headed. Health is always a concern but never a given. Not know, not in 2020.

Heyward is leaning on this fraternity of brothers to get through this mess, and they are going to have a little bit of fun while they’re at it.

“I think that's what we've been doing. Just having fun competing," he said. "We have to show up every day. Yes, it's our job. But we want to have fun doing this because there are worse places to be. There are people that are in worse off positions than we are right now struggling in so many ways. So we know we're bringing something to them to watch it on TV. But we're also going out here because we love the game of baseball.”

And the healing is constant with this team. It’s a clubhouse that remains transparent and eager to learn. Prior to the season, they even had speakers come in to discuss race, a subject that becomes more important as the season unfolds.

Every single ballclub is made up of a group of guys from all over the world, and it’s not always cohesive.

The Cubs’ leader came to the conclusion that through COVID, a shortened season and civil unrest taking place constantly in this country, there is one thing that they can guarantee.

“Putting it all out there,” Heyward said. “I would say at the end of the day, everyone came back to the conclusion of, no, we're a family, we're together.”