30. Andrew Miller, 2014: Four Years, $36 Million
Miller didn't make it to the end of his Yankees contract in pinstripes, dealt to Cleveland midway through the team's 2016 sell-off. Predictably, he dominated that postseason as a multi-inning weapon, earning ALCS MVP honors by hurling 7.2 innings, whenever he was needed, and racking up 14 Ks.
The next October, of course, he let the Yankees back into the ALDS by surrendering a home run to Greg Bird, left-on-left, while holding a two-games-to-none lead. The Yanks won the series. Miller never got his due in the Bronx, and the 2015 team has been largely forgotten, but this deal was a great one.