2. Jason Heyward
There is a strong argument for Jason Heyward to be number one on this list, as the Cubs are going to be paying him $22 million in 2023 to not even play for them.
Heyward, formerly of the Braves and Cardinals, signed with the Cubs before their 2016 World Series campaign and has massively underperformed his 8 year, $184 million deal. When signing with the Cubs, he sighted the young core of the club as a major draw for him. The Cardinals “old core” has outlasted both Heyward and that core he cited.
In 2022, Heyward has slashed .202/.278/.277 while appearing in just 48 games for Chicago. He is still a capable defender in the outfield, but has not had an OPS over .627 since 2020. He’ll likely get a shot as a fourth outfielder on another team next year, but he will never be the guy that the league thought he’d develop into.
For Chicago, it makes sense to let Heyward walk in order to free up playing time for young guys. But it is still an awful contract to eat and will surely frustrate ownership.