The Cubs are still on the hook for millions from this all-time free agent disaster.

The 2023 season was the final year of Jason Heyward’s big deal with the Chicago Cubs. The richest deal in franchise history, signed 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 final competitive window – so Cubs fans will be disappointed to learn that the team isn’t finished paying the veteran outfielder.

Yes, last year was the final lump sum payment on the eight-year, $184 million agreement. However, in digging through some specific payroll statistics from Spotrac, I discovered that the Cubs are still obligated to pay Heyward $5 million in deferred payments from 2024 to 2017.

Now, that will not count against the Cubs’ luxury tax payroll number or anything else, but ownership has repeatedly stated that every dollar spent, whether it hits the CBT number or not, is very important to the Ricketts family and may have an impact on the baseball operations budget.

Source: Bellinger returning to the Cubs on $80M, 3-year deal

Former Cubs outfielder Jason Heyward has set his eyes on another ring.

Heyward, meanwhile, appeared to get his career back on track last year with the Dodgers, posting a 117 OPS+ in a more matchup-oriented role in the Los Angeles outfield. He re-signed with the club this winter and joins a team that has the potential to be historically good following the most expensive offseason in MLB history.

Heyward’s performance in 2016, specifically his rain delay statement in Game 7 of the World Series, earned him a lot of leeway with fans even today. However, considering the production the Cubs anticipated for when they signed him from the division rival Cardinals, as well as the money they paid him, it’s logical to assume they expected him to play a much larger part than he did in Chicago.

At least in three years, we’ll be able to declare for sure that the Chicago Cubs are done paying Jason Heyward… (11 years after signing him).

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