7) Drew Smyly
Smyly is a simple case, in fact much simpler than Contreras. He could easily find himself higher on the list, but the dollar amount is low enough to rank below some of these other names. He also retains the potential to live up to the deal, unlike some of the names above him. Smyly pitched well for the Cubs in 2022 to earn a new contract worth $19MM split between 2023 and 2024. It seems likely that he will exercise his $8.5MM player option for 2024, considering how terrible he's been in 2023.
Smyly's 2023 has been a disaster compared to his first season in Chicago. In 21 starts, his ERA sits at 5.01. Smyly has actually been lucky, as advanced metrics suggest he could be even worse than the surface indicates. Smyly is allowing baserunners like never before, as evidenced by his higher walk rate. He was recently demoted to the bullpen.
Now 34, it seems unlikely that he'll have some sort of career renaissance. Smyly will make $8.5MM next year, and he may not even do it as a member of the Cubs organization. He doesn't have a guaranteed spot in either the rotation or the bullpen. The only silver lining for the Cubs here is the low commitment in both years and dollars.