One of Jason Heyward’s most memorable moments with the Chicago Cubs remains what happened behind closed doors.
His rain-delay speech in a players-only meeting before the 10th inning of Game 7 in the 2016 World Series before the Cubs went on to beat the Cleveland Indians 8-7 is of legend. Since signing an eight-year, $184 million contract before the Cubs’ championship season, Heyward, 31, hasn’t put up the offensive numbers expected with that type of contract. Yet despite his struggles, Heyward has become a key leader on the Cubs and, within the last year, more vocal.
The process getting to this point, however, hasn’t been easy.
“I still just never believed that the contract itself was something that I battled with,” Heyward told the Tribune earlier this month. “I just battled with the fact that in my mind I’m on the other side of things now. To sign to this amount of money, I took less to come here, had some other options, just had one of the best years of my career the year before in the same division. That year (2015) I started off slow as well.
“So just knowing (the Cubs) watched that I’m like, all right, so why don’t I get to struggle now? Why can’t I go out here and play Gold Glove defense and just try to win? We’re talking about a 108-year curse at the time. Those are all questions that crept in. That played more of a nuisance to me than the contract.”
Inconsistent playing time wasn’t something Heyward experienced in his six seasons before joining the Cubs. Good or bad games, Heyward knew he would be in the lineup the next day. Heyward said it took time for him to get past that growing pain. He has enjoyed playing for former teammate and now-manager David Ross, whom Heyward says puts winning first.
“Not that Joe (Maddon) didn’t put winning first,” Heyward said. “Not that any organization these days doesn’t put winning first, but they do try to label things a lot faster, and that can take away from someone like myself.”
Through it all, Heyward has maintained the same persona off the field and in the process become more than someone who just leads by example on the field. His voice became amplified last summer when speaking out about racial injustice following the killing of George Floyd and the Black Lives Matter movement. Stepping into a bigger leadership role with the Cubs and working with local organizations has been part of his evolution.
Heyward now lives in Chicago year-round and is getting involved with community initiatives. One is Future Ties, located on the South Side, that supports low-income families by offering after-school and summer programs for children. Another, By The Hand Kids Club on the city’s Far West side, Heyward and his wife spent time at over the offseason. They participated in Austin Harvest, where the club bought out a liquor store, renovated the space and turned it into a fresh market at which kids work and take ownership of the enterprise.
“For me, someone calling Chicago home now, I know one day that’s going to benefit my kids too,” Heyward said. “The city is gradually becoming a better place and certainly that’s actually happening.”
With the Cubs playing so many day games at Wrigley Field, it’s similar to having normal 9-to-5 work hours. Heyward has appreciated how it has allowed him to explore and enjoy Chicago too.
“Honestly, I feel like it just happened organically,” Heyward said of showing more sides of himself. “Because they care about good people because they know the game of baseball on the field, they’ve seen so much history. I feel like they take it for granted a lot less in the Midwest for sporting events. It just naturally happened. I got to live life for once.
“As an athlete, the way the city respects our space, the way they appreciate having us around, it lets you just naturally open up.”
Those within the Cubs organization haven’t overlooked how Heyward has evolved in the last five years. During the offseason, Heyward was among the first to reach out and welcome outfielder Joc Pederson and third-base coach Willie Harris to the organization, even surprising Pederson with a phone call.
Cubs president of baseball operations Jed Hoyer called Heyward a natural leader and believes part of him being more vocal within the clubhouse stems from getting older and the respect he always has commanded through his work ethic. Leadership skills can be tough to quantify in a sport that values advanced metrics and data.
“You know when you see it,” Hoyer told the Tribune. “Everyone has looked up to him so much. They know how much work he puts in and how much he cares.”
Cubs shortstop Javier Baez described Heyward “as one of my brothers” for how he always has looked out for him and cares about his family. Baez said Heyward traveled to Puerto Rico to visit him before the pandemic.
“That’s the type of brother and leaders you want on your team because they want to have the best for you,” Baez told the Tribune. “He cares about me being a good person.”
In some ways, becoming a more vocal veteran was inevitable for Heyward. Ross witnessed his maturation firsthand, sharing a clubhouse in Atlanta through Heyward’s first three years in the majors. Heyward has been around good players and good leaders throughout his career, Ross said, and was brought up to respect the elders on the team.
“And now, he’s that guy,” Ross said.
Heyward still has three years left on his contract, including this season. This team could look very different in the coming months. By the start of next year, he could be tied with catcher Willson Contreras as the second-longest-tenured Cub behind right-hander Kyle Hendricks.
“I feel like it’s just my time, my responsibility,” Heyward said, “to be one of those people that pass things along to the next generation of players.”