Jesse RogersMar 27, 2026, 01:47 PM ETCloseJesse joined ESPN Chicago in September 2009 and covers MLB for ESPN.com.Follow on XMultiple Authors
Heyward, 36, played for five teams after breaking in with the Atlanta Braves in 2010. His final stop came in San Diego last season where he appeared in 34 games for the Padres.
He won his first World Series ring with the Chicago Cubs in 2016, where he signed an 8-year, $184 million contract before the start of that season. It remains the largest deal in franchise history.
After seven seasons in the Windy City, Heyward joined the Los Angeles Dodgers in 2023. The next season, he spent 63 games with L.A. before being designated for assignment and finishing the year with the Houston Astros. The Dodgers later presented Heyward with a 2024 World Series ring for his contributions to the team’s championship run while wearing the blue and white.
Several years before retiring, Heyward opened a youth baseball academy in Chicago that he will dedicate even more time to now that he’s done playing.
“I wanted to reach this moment and know without a doubt that it was time to walk away, and I do,” Heyward said in a Friday news release. “No second-guessing, no looking back, just gratitude.
“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.”
Heyward’s most famous moment may have come in the weight room as opposed to the baseball diamond — specifically the visiting weight room at Cleveland’s Progressive Field. During Game 7 of the 2016 World Series — during a rain delay before the 10th inning — he gathered his team together after the Cubs blew a late game lead to Cleveland. After his “114-win” speech, the Cubs went on to beat Cleveland 8-7 in 10 innings, ending a 108-year championship drought for the franchise. Heyward was credited for calming things down after chaotic eighth and ninth innings for his team.
Jesse RogersMar 27, 2026, 01:47 PM ETCloseJesse joined ESPN Chicago in September 2009 and covers MLB for ESPN.com.Follow on XMultiple Authors
Jason Heyward has announced his retirement after 16 seasons spent with the Braves, Cardinals, Cubs, Dodgers, Astros and Padres.He is an All-Star, 5x Gold Glove Award winner and 2016 World Series champion. pic.twitter.com/oKaNASvOUh
World Series champion Jason Heyward officially retired on Friday after a 16-year big league career.
CloseJesse joined ESPN Chicago in September 2009 and covers MLB for ESPN.com.Follow on X