2014 – Orioles sent Eduardo Rodriguez to Boston Red Sox for Andrew Miller
This one goes down as a win and loss. The Baltimore Orioles know that Miller was the best bullpen arm available and that he was going to someone in the American League, maybe New York, maybe Detroit.
The Orioles swooped in and took him, sending away a promising left-hander in Rodriguez.
Miller, of course, helped carry the bullpen in the playoffs until the offense faltered against Kansas City. However, Miller was outstanding for the Orioles, even if he was a rental.
But, trading away the best left-hander in the system hurts. Rodriguez was struggling for the Bowie Baysox in 2014 with knee problems, something that has continued to affect him in Boston.
But, Rodriguez is under Red Sox’ control until 2022. He certainly would be a great piece in the Orioles’ rotation right now, and probably represents the pitcher who could have been the best for Baltimore on this list. But, getting Miller was a move to go for it in 2014, and it almost worked.