Lance McCullers Jr.
This is a tough one because, on balance, Lance McCullers Jr.'s contract extension was a good idea when it was signed back in 2021. Houston penned him to a five year, $85 million deal despite the fact that he had to have Tommy John surgery and missed the 2019 season. When he has been on the mound, the results have been very good and Lance clearly wanted to be in Houston.
The problem, of course, has been his health. Aside from his Tommy John surgery which shouldn't be a dealbreaker in this day and age, McCullers Jr. has never exactly been an innings workhorse. His career high for innings in a season by a mile was 2021 where he threw 162.1 innings and finished in the top 7 in Cy Young voting with the next closest mark being 128.1 innings in 2018.
Lance's tendency to be dinged up has proven to be problematic since 2021. Again, the results were still good when he was on the mound as he had a 2.27 ERA in his eight starts in 2022, but arm troubles limited him to those eight starts and he was out for all of 2023 after having surgery to repair his troublesome flexor tendon and to take out a bone spur in his throwing elbow.
Could McCullers Jr. come back in 2024 and be good enough to justify the $17 million is going to make next year? Absolutely. However, betting on him staying healthy may not be the wisest decision and that is a lot of payroll space being taken up by a big question mark.