9. Gerrit Cole
In the 2019 offseason, the Yankees finally got their target to anchor their rotation for years to come. After years of striking out on aces via trade, the Yankees shelled out the money to sign a guy, who at the time was a top three pitcher in Gerrit Cole, to a massive nine-year $324 million dollar deal.
Everyone knew it was an overpay at the time, but that’s really how free agency works. You’re in a bidding war with 29 other teams so you have to be able to beat the other offers.
In Cole’s first year as a Yankee, he was dominant, posting a 2.84 ERA in 12 starts in the 2020 season. He looked like the best pitcher in the American League for much of 2021 until the sticky stuff crackdown took place. Cole was still good after that, but not the elite Cole we had seen in Houston and the first year in New York.
This season, Cole has gone 9-6 with a 3.41 ERA in 25 starts. It seems like he puts a couple of very good starts together followed by an awful start. The inconsistency is not something you want from a guy making over $30 million dollars annually.
Cole is making $36 million dollars in 2022 and the same for every season through the 2028 campaign. Cole will be 37 when the deal is up. He’s still an ace but is not worth anything close to the deal he is getting.