4. Jameson Taillon: $18 million
If Taillon continues to perform the way he did in 2023, this contract will continue to look really bad for Jed Hoyer. The 32-year-old starting pitcher was supposed to come in and provide stability to the Cubs' rotation. But the WAR of -0.1 and 4.84 ERA in 2023 don't exactly inspire confidence for Taillon's future.
With three more years left on his deal, Taillon needs to step up in a big way next year to earn his $18 million in my eyes. With Marcus Stroman likely departing in free agency and the Cubs depending on young starters, critical eyes will be on each one of Taillon's starts next year.