2) Not getting rid of Jason Heyward sooner
The Jason Heyward contract was a bad contract from day one. He finally stepped it up offensively in 2019 and 2020 … but he was not good in 2021 and he was injured.
In 2022, he was injured again and awful at the plate again. The straw that broke the camel’s back this year was that this is the first year that Heyward was not an above-average defender, at minimum.
Fortunately, the Cubs have said that they are going to be getting rid of Heyward and not having him on the team for the final year of his contract.
However, if they would have been able to trade him (by eating some of his contract) or just release him earlier, then the Cubs would have been able to either sign someone on the market that’s much better than Heyward, like Starling Marte, or trade for one. They could have even turned to one of their prospects, like Christopher Morel or Brennen Davis.