Jason Heyward walks up to the plate on an 84-degree night at Wrigley Field to the tune of “Having Our Way” by popular rap artists Drake and the Migos. 

The Cubs right fielder taps home plate one time as the lyrics, “‘I’m having my way, set out here having his way, and like the third Migo I…take” blasts from the sound system at Wrigley Field. 

Heyward’s first tattoo was of the Chicago cityscape tattooed on his right shoulder, which came in 2019. The 32-year-old is strategic when it comes to his ink and his music; they’re a way for Heyward to express himself and have been a great release.

On Heyward’s left calf, there’s a tattoo of the word ‘success’ in block letters spelled out vertically. The Georgia native posted a picture of the tattoo to his Instagram account and attached the song of the same word – written by Jay-Z. 

“He always comes with the real – right, good, bad or indifferent. He gives it to you straight and he holds himself accountable,” Heyward says.

The song was originally released on November 6, 2007, only six months after Heyward was drafted out of high school. But the content of the song – which details the pitfalls of success – stuck with Heyward.

“People don’t realize that when you have success in life, what comes with that. Not so much how it changes you, the person, initially, but the way people treat you. People treat you differently,” the five-time Gold Glove winner says. “You become jaded by certain things because your normal peace of mind doesn’t exist anymore.”

That’s why the song ‘Success’ by Jay-Z stuck with Heyward enough for him to get it tattooed on his left calf in block letters. The song itself deals with the pitfalls of fame and fortune. The song was released right as Heyward found his own success – selected 14th overall in 2007 by the Braves right out of Henry County High School in Georgia. 

“When you attain a certain level of fame, almost as if you’ve ventured into another world,” Heyward said. “You become larger than life.”

Growing up, Heyward didn’t have the same shoes that some of his classmates had on their feet. 

“Seeing other people, other kids that I was going to school with, like where they had the [Air] Forces, they had the shoes, they had the fits, but my parents were putting that money elsewhere to get me ahead in life,” Heyward said. 

Heyward’s ability to sacrifice and his passion for giving back are both rooted in the lessons he learned during his childhood.

“I feel like it comes from my parents, Eugene and Laura,” Heyward told Marquee Sports Network’s Elise Menaker. “Always wanting to make sure we earned what we have in life, but help people if you can. Treat people how you want to be treated. Know that manners will take you where money won’t.”

Since signing with the Cubs prior to the 2016 season, the World Series champion has left his mark on Chicago. The 12-year-veteran helped fund the ‘Austin Harvest’ and teamed up with 2020 Cubs first round draft pick and Chicago native Ed Howard and 2018 first round draft pick Nico Hoerner to ensure  The Players Alliance Pull Up Neighbor Tour was successful on Chicago’s South Side. The trio handed out materials to help fight COVID-19, food, and baseball gear for youth.

Heyward was also one of more than 100 MLB players to donate their game checks on Jackie Robinson Day which supported the Jackie Robinson Foundation and The Players Alliance. The funds assisted in getting baseball equipment to Black communities, and a scholarship fund through The Player’s Alliance.

Heyward continues to be heavily involved in the community and recently announced a partnership with the By The Hand Club to open the Jason Heyward Baseball Academy as part of a 150,000+ square-foot sport, wellness and education facility in the North Austin neighborhood. 

“A lot of people in my position get asked questions on what can we do different for baseball,” Heyward said. “What can we do to help the city grow or change or help violence die down? I think it’s to take action, come together with people and build facilities like this.”

Heyward will serve as director of the program, and with the help of his personal staff of coaches, will mold young people into athletes and leaders in their communities.

“My wife V [Vedrana], she and I have a passion for helping people,” Heyward said. “There’s no better place to start than the community we want to start a family in one day and have our kids grow to be a part of it and see something special that we left behind to take notice and realize that it’s ok to help people on your way to having success and having fun and enjoying life.”

Heyward hopes the 10-acre campus will help ease the stress on youth in the area. 

“I want them to run to this and see it as an opportunity to have peace of mind and to see something different on a daily basis,” Heyward said.