1. Trevor Bauer
What more can you say about Trevor Bauer that hasn’t already been said? Ideally, nothing. It would be very pleasurable to not address him whatsoever.
Any time you set a record for obtaining money, then don’t even stick around to complete your first season of obtaining that money, you’ve earned the No. 1 spot on this list and any list that may someday follow it.
Last offseason, the Dodgers triumphantly defeated the Mets in one-on-one combat for Bauer’s hand, coming out on top with a three-year, $102 million deal that included a player option for 2022.
Spoiler alert? That onerous player option has already been picked up, even though there’s little chance of Bauer making it to the mound in LA this year. Facing two criminal accusations of sexual assault, Bauer ducked out of the 2021 season with an 8-5 record and 137 strikeouts in 107.2 innings pitched, and those numbers will likely represent his final line for the franchise.
Whenever a record-setting contract results in a player’s legacy being wiped from the record midway through his first campaign in uniform, that deal should rest comfortably atop any list of this sort. Unless the Dodgers extend the olive branch to OJ Simpson to cap this offseason with a seven-year deal, we can’t foresee them topping the massive mistake.