On October 25, 2016, Heyward, along with teammates Dexter Fowler, Addison Russell, and Carl Edwards Jr., became the first African-Americans to play for the Cubs in a World Series game. Heyward was credited with leading an inspiring players-only meeting during a 17-minute rain delay near the end of Game 7 of the 2016 World Series. The Cubs eventually won the game 8–7 after 10 innings, and gave them their first World Series championship in 108 years. On November 9, Heyward became the first position player in Major League Baseball history to win three straight Gold Glove Awards with three different teams (Braves, Cardinals, and Cubs).