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Former Cubs Outfielder Not Surprised Team Only Won One World Series

Originally posted on Athlon Sports | By Sam Bernardi | Last updated Apr 8, 2025 6:00 AM ET

Jason Heyward was not an all-time Chicago Cub. After signing an eight-year, $184 million contract before the 2016 season, the all-around outfielder struggled to live up to his payday.

Heyward’s stats were underwhelming as his seven years in Chicago yielded 162-game averages of 13 home runs, 63 RBIs, a .245 batting average, a .700 OPS, and an 85 OPS+. Heyward was touted as a two-way star during his free agency, and while his defense was terrific, he never quite electrified Wrigley Field like he had earlier in his career.

However, Heyward’s first year also saw the Cubs break that infamous 108-year World Series drought. The jubilation was slightly marred by fan expectations of another, if not multiple, championships to follow.

Heyward recently provided insight as to why those expectations were unrealistic and how difficult it is to win in this league.

Here’s what he told reporters, via CHGO Cubs:

Jason Heyward talked to @thecarm on the debate Cubs fans have about not winning another World Series after 2016 with that core group:

“You gotta understand and know like how hard it is to win one.” pic.twitter.com/0SPkVSQvEN
— CHGO Cubs (@CHGO_Cubs) April 7, 2025

“It’s been a while since a team’s won back-to-back… You have to have a lot of things go your way,” Heyward added.

The fans were not completely in the wrong. Key returnees from that 2016 squad included captain 1B Anthony Rizzo, NL MVP 3B Kris Bryant, SP Jon Lester, SP Jake Arrieta, and SP Kyle Hendricks. Winning another was not out of the realm of possibilities.

That 2017 version of the Cubs lost in the championship series to the Los Angeles Dodgers, so it’s not as if they were a complete failure. In fact, Chicago had made the NLCS every year from 2015-17, the only three-consecutive occurrence in franchise history.

Heyward also emphasized the degree of difficulty of going back-to-back as the Yankees from 1998-00 are the last club to defend their crown. Uncontrollables like luck, health, and postseason draw can all play a factor during that time of year.

Cubs fans will likely never put this harmless debate to rest because while those NLCS losses may have been painful, the 2016 World Series banner flies forever, and they should always cherish that magical run.

This article first appeared on Athlon Sports and was syndicated with permission.

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