Chicago Cubs Still Paying Former MLB Player $5 Million Per Year

Jason Heyward, who helped the Cubs win the 2016 World Series, is still receiving deferred payments from the team.

Mar. 29, 2026 at 7:19am

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The Chicago Cubs are still paying former MLB player Jason Heyward $5 million per year through the 2027 season, even though Heyward retired from baseball earlier this week. Heyward played for the Cubs for seven seasons, helping the team win the 2016 World Series Championship.

Why it matters

Heyward's long-term deferred payment deal with the Cubs highlights the complex financial arrangements teams sometimes make to sign and retain top talent, even after a player's retirement. This story provides insight into the business side of professional sports and the lasting impact star players can have on a franchise, even after they stop playing.

The details

According to reports, the Cubs deferred all of Heyward's $20 million signing bonus, which is being paid out in four $5 million annual installments from 2024 to 2027. Heyward spent the longest tenure of his 16-year MLB career with the Cubs, batting .245 with 62 home runs, 289 RBIs, 335 runs, and 32 stolen bases during his seven seasons with the team.

  • Jason Heyward announced his retirement from MLB earlier this week.
  • The Cubs beat the Washington Nationals 10-2 on Saturday, March 29, 2026.
  • Heyward will receive his final $5 million deferred payment from the Cubs on April 1, 2027.

The players

Jason Heyward

A former MLB outfielder who played 16 seasons in the league, including seven with the Chicago Cubs where he helped the team win the 2016 World Series Championship.

Chicago Cubs

A professional baseball team based in Chicago, Illinois that plays in Major League Baseball's National League.

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What they’re saying

“The Cubs deferred all of Jason Heyward's $20 million signing bonus, paid in four $5 million installments, each April 1, 2024-27.”

— Mike Mayer, Writer, Metsmerized Online

What’s next

The Cubs will look to win the series against the Washington Nationals on Sunday, March 30, 2026.

The takeaway

This story highlights the complex financial arrangements professional sports teams make to sign and retain top talent, even after a player's retirement. Jason Heyward's long-term deferred payment deal with the Cubs shows the lasting impact star players can have on a franchise, even years after they stop playing.