Heyward, who homered in his first MLB at-bat, won five Gold Gloves and two World Series rings
By Matt Snyder Mar 27, 2026 at 1:18 pm ET • 2 min read 
Getty Images On Friday, Jason Heyward officially announced his retirement from Major League Baseball. He played in parts of 16 seasons, appearing in 1,824 games in the regular season as well as 45 playoff games. Heyward plans to now focus on his youth baseball academy in Chicago.
"I wanted to reach this moment and know without a doubt that it was time to walk away, and I do. No second-guessing, no looking back, just gratitude," Heyward said in a statement. "Sixteen years in this game gave me everything, and now I get to give some of that back. Through the Jason Heyward Baseball Academy, I get to mentor the next generation, keep my hands in the game, and make sure kids in my community have the opportunities and the space to dream the same way I did. And it does not stop there. Staying connected to the younger guys coming up through the league and being a resource for them as they navigate this game matters to me just as much. It's been a heck of a career. It's been a blast."
Heyward was a first-round pick (14th overall) out of high school in 2007. He debuted to great fanfare as the top prospect in baseball in 2010 and didn't waste much time in making an impact with a three-run shot of All-Star lefty Carlos Zambrano.
He would finish second in NL Rookie of the Year voting to future Hall of Famer Buster Posey that season. Heyward posted 6.4 WAR as a rookie and made the All-Star team. He amassed 29.9 WAR through his age-25 season.
Heyward then landed an eight-year, $184 million deal with the Cubs, and they won the World Series in his first season. Heyward is credited by teammates for a speech during a Game 7 rain delay that helped rally the troops and lead to a 10th-inning rally that secured the first Cubs title since 1908.
Heyward's numbers at the plate waned in light of the early promise and prospect hype, but he long earned his keep with exceptional defense (winning five Gold Gloves), good-to-great baserunning and was one of the most heralded clubhouse guys in baseball.
All told, Heyward hit .255/.336/.408 (101 OPS+) with 1,575 hits, 306 doubles, 41 triples, 186 home runs, 730 RBI, 879 RBI, 125 steals and 41.5 WAR. He'll make the Hall of Fame ballot in five years but does not figure to get serious consideration. Still, it's always a feather in the cap of a player to make the ballot. In addition to the Cubs and Braves, Heyward also spent time with the Cardinals, Dodgers, Astros and Padres.
Heyward ranks 53rd all-time among right fielders in career WAR, sitting around players like Darryl Strawberry, Nelson Cruz, Ken Singleton, Tim Salmon, David Justice and Reggie Sanders. Even if the bar was set far too high with the hype and that first at-bat and even the entire rookie season at age 20, Heyward ended up putting together a terrific and lengthy career.
He now retires with two World Series rings (2016 Cubs and 2024 Dodgers) and an admirable post-career plan.
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