Cubs still on the hook for millions to this all-time free agent bust

Despite his contract finally coming off the books, the Cubs will continue to pay a 2016 World Series hero through the end of the 2027 season.

Milwaukee Brewers v Chicago Cubs - Game Two
Milwaukee Brewers v Chicago Cubs - Game Two / Jon Durr/GettyImages

The 2023 season marked the final year of Jason Heyward's massive contract with the Chicago Cubs. The richest deal in franchise history inked before the historic 2016 season, quickly felt like an anchor weighing down the front office and its ability to make impact additions at key points during the team's last competitive window - so Cubs fans will be less than thrilled to know the team isn't done paying the veteran outfielder.

Sure, last year was the final lump sum payment on that eight-year, $184 million deal. But while digging around some detailed payroll information from Spotrac, I noticed the Cubs are still on the hook for $5 million in deferred payments due annually to Heyward from 2024-2027.

Now, that won't count against the Cubs' luxury tax payroll number or anything like that, but ownership has repeatedly made one thing abundantly clear: every dollar spent, whether it hits the CBT number or not, is very much in the minds of the Ricketts family and could impact the baseball operations budget.

Former Cubs outfielder Jason Heyward has sights set on another ring

Heyward, meanwhile, seemed to get his career back on track last year with the Dodgers, putting up a 117 OPS+ in a more matchup-based role in the Los Angeles outfield. He re-upped with the club this winter, and joins a team that could be historically good on the heels of the highest-spending offseason in baseball history.

Heyward's role in 2016, namely his rain delay speech in Game 7 of the World Series, buys him a lot of leash with fans even to this day. But given the production the Cubs hoped for when they poached him from the division rival Cardinals and the money they doled out, it's certainly safe to say they expected him to play a much larger role than he did during his time in Chicago.

At least in three years, we can say once and for all: the Chicago Cubs are done paying Jason Heyward... (11 years after they initially signed him).

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