Interesting. Ubaldo scuffled a bit in Cleveland, but rebounded with a solid 2013 season. 1.09 ERA as Cleveland was 6-0 in his September starts that year, including beating the Twins on the last day of the season as they claimed a postseason berth by just 1 game. They also got pick #31 in the 2014 draft as compensation for Ubaldo leaving as a free agent, and they selected Justus Sheffield who they used to get Andrew Miller. Given that is also took Pomeranz 5 years and 2 additional trades to do much, I'd say Cleveland did all right there. Obviously DeRosa didn't provide comparable benefits, although they did manage to flip him for Chris Perez who at least had a couple seasons as a decent closer. And it took Archer another trade before he broke through (and arguably, he's never really broken through to be an ace in MLB). A bad trade, but perhaps not one that really hurt them -- they haven't really been held back by a lack of rotation depth the past few years. Same goes for missing out on Pomeranz.