1) Cleveland acquires Andrew Miller, trades Ben Heller, Clint Frazier, J.P. Feyereisen and Justus Sheffield (2016)
Arguably the most pivotal move the Guardians front office has pulled off in the last decade, Andrew Miller became a staple of the then-Indians’ bullpen. Sure, they didn’t end up winning a World Series, but he was a massive part of the run in 2016 and the record-breaking 2017 regular season. Championships matter, but a better lineup that could have won it all would have made this move one of the best in the history of baseball.
The outlook of the trade becomes even better when looking at what the Guardians gave up. Cleveland is not a franchise willing to gut a farm system for one or two players, but this trade went against that philosophy – and worked. Ben Heller played in just 31 MLB games, J.P. Feyereisen is a solid bullpen arm, but nothing special (and he plays for the Tampa Bay Rays) and Justus Sheffield is still REALLY trying to find his way in the big leagues for the Mariners.
Clint Frazier, the once-promising star outfielder and key part of the Miller trade, flamed out in New York and is toiling away with the Chicago Cubs. All in all, Cleveland bet on themselves, somewhat stripped their farm system of high-caliber prospects, and benefitted with a World Series run and a regular season of 100+ wins. New York doesn’t have any of the players swapped out for Miller anymore.