2016: Andrew Miller
Another trade-away! Let's keep these rolling. The Yankees missed the playoffs in 2016 and were nothing to write home about, but they had a monster bullpen that featured Chapman, Dellin Betances and Andrew Miller. In fact, the four-year, $36 million contract given to Miller after the 2014 season might've been Cashman's best work!
But then came the trade deadline, and the Yankees determined they would be sellers (smart move). Chapman was sent to the Cubs in a deal that included Gleyber Torres, and Miller was sent to Cleveland (who met Chicago in the World Series that year!) for a package of Justus Sheffield, Clint (Jackson) Frazier, Ben Heller and JP Feyereisen. Guess how many of those guys from the Miller deal are with the organization today? None!
In fact, Sheffield reportedly prevented the Yankees from acquiring Manny Machado (because Cashman didn't want to get rid of him, but was fine trading him for another pitcher on this list!). Frazier's time in the Bronx was mired in controversy and disappointment. Heller was nothing more than bullpen filler. Feyereisen was traded again and then got good with the Rays (he's a Dodger now).
Miller would've REALLY helped on the 2017 Yankees, huh? When they couldn't score runs against the Astros and needed the pitching staff to be nails? Oh, what do you know, he was an All-Star in 2017 with Cleveland and finished with a 1.44 ERA, 1.99 FIP and 0.83 WHIP. It wasn't until 2018 that his career went off the rails.
But, yeah, 2017 could've been that much more special had Miller been in pinstripes.
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