Powered by Roundtable

A 2016 World Series champion's storied 16-year MLB career concludes. Heyward's impact beyond the box score cemented his legend.

Former Chicago Cubs World Series champion Jason Heyward calls it quits after 16 Major League seasons. 

Heyward officially announced his retirement on Friday morning after a long career. He played 16 years in the big leagues and began his Major League career at just 20 years old with the Atlanta Braves. 

Following a few seasons with the Braves and one season with the Cardinals, Heyward eventually signed a big contract with the Cubs during the 2016 offseason. 

He agreed to an eight-year, $184 million deal with the North Siders in December of 2015. That $184 million contract remains the largest deal that the Cubs front office has given out in the team’s history. 

At that time, this was one of the Cubs' biggest moves in history. Heyward accumulated a 29.9 WAR in his first six Major League seasons and was coming off a 7.0 WAR season with the Cardinals in 2015. 

Unfortunately, Heyward never really lived up to the massive contract he signed with the Cubs. He finished with under a 2.5 WAR in each of his seven seasons in Chicago and had a combined 9.1 WAR over those seven years. 

Heyward was never really a difference-maker during his time with the Cubs. The New Jersey native hit just .245 with 62 home runs, 111 doubles, 289 RBI, and 32 stolen bases across 744 games from 2016 to 2022. 

Despite the fact that Heyward signed an eight-year deal back in 2015, the Cubs actually released the outfielder with one year left on his deal. After hitting just .204 across 48 games in 2022, it was time to move on from him. 

There wasn’t much good that came out of the Heyward era in Chicago. He struggled offensively, his power numbers were down, and he didn’t contribute much to the Cubs during his seven years. 

However, Heyward will always be remembered in the city of Chicago. 

He is one of the biggest reasons the Cubs broke the 108-year World Series drought. Heyward called a players-only meeting during a 17-minute rain delay in Game 7 of the 2016 World Series. The Cubs had just blown a three-run lead in the eighth inning, and Cleveland had all the momentum heading into the last inning. 

So, Heyward stepped up. 

He delivered a motivational speech to his teammates in a small weight room in the visitors' locker room. The Cubs then went out to the field, scored two runs in the 10th inning, and broke the Billy Goat curse. 

While Heyward might have never lived up to his contract, he is a Cubs legend for his pivotal role in breaking the World Series drought.