15 worst Chicago Cubs free agent signings in franchise history

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2. Jason Heyward - Eight Years, $184 Million (2015)

The fact the largest free agent contract in Cubs history ranks this high on a list of the worst free agent signings in franchise history is hardly encouraging. But, hey, at least Jason Heyward's rain delay speech played a role in that Game 7 comeback in 2016, right?

Speech or no speech, there's no way to paint this contract as worth its weight. From the onset, Heyward couldn't figure it out at the plate. The fact he won back-to-back Gold Gloves in the first two years of the deal made things at least a bit more palatable, but his inabilty to replicate the offensive numbers from earlier in his career left a bitter taste in folks' mouths.

The year before coming to Chicago, Heyward put up big-time numbers for the rival Cardinals, slashing .293/.359/.439 - good for a 117 OPS+. That type of production, paired with his elite defensive work, made him look like a game-changer in free agency. But that hardly proved to be the case.

During his seven years with the Cubs, Heyward managed just an 86 OPS+. Late in the 2022 season, Chicago made clear its intentions to cut ties with the veteran - and he latched on with the Dodgers this winter via a minor league deal.

Production that fell well short of expectations and the fact his contract kept the front office from making necessary additions during the peak of the competitive window give Heyward the number two spot on this list, despite his outstanding contributions in the clubhouse and community.