10. Brandon McCarthy: Four Years, $48 Million, 2014
McCarthy was another rare miss for Friedman's front office, occurring in his first offseason at the helm. Best to get 'em out of the way early.
The mercurial right-hander was coming off an extremely successful run with the New York Yankees following the 2014 trade deadline (7–5 with a 2.89 ERA in 14 starts), and Friedman got suckered into paying for past performance and ignored the injury concerns along the way.
McCarthy missed significant time with the Texas Rangers early in his career rehabbing both elbow and shoulder issues, which prevented him from becoming one of the game's top young pitchers. Ultimately, he made just four starts with the 2015 Dodgers and nine with the 2016 team, having Tommy John surgery in between on April 30, 2015.
He recovered to post a solid 92.2 innings for the 2017 Dodgers, but his only World Series appearance featured a George Springer dinger and the loss in Game 2.