11. Scott Kazmir - three years, $48 million, 2015
A trio of "what" here. Scott Kazmir for three years and $48 million after the 2015 season? The left-hander was admittedly rediscovering his form a bit, but his 2014 All-Star season came in the spacious Oakland Coliseum, and his post-trade deadline showing in Houston in 2015 was pretty bad. He ended up pitching 26 games for the Dodgers in 2016, didn't take the mound again until 2021 because of injuries, and was done after five games with the Giants that year.
10. Brandon McCarthy - four years, $48 million, 2014
Again ... what?! McCarthy, for the first time in years, logged a fully healthy season and was impressive in his 14 starts with the Yankees following the 2014 trade deadline. Good for him! But $12 million per year across FOUR years heading into his age-31 season knowing the injury history? Maybe Andrew Friedman's worst signing? McCarthy pitched in 155.2 innings with the Dodgers from 2015-2017 before LA traded him to the Braves. He retied after 2018.
9. Rich Hill - three years, $48 million, 2016
Dick Mountain was another Friedman signing after he came over from Oakland and logged a 1.83 ERA and 0.79 WHIP in six post-deadline starts in 2016. Then, from 2017-2019, Hill couldn't stay healthy, pitching in 63 games. Not bad, but not $16 million worth of pitching annually. Well, if you factor in his postseason appearances (2.70 ERA in 12 games totaling 50 innings with the Dodgers), that probably justified it all. He's still hanging around, too. The soon-to-be 43-year-old will be enjoying Pittsburgh in 2023.