July 14th, 2016: Red Sox acquire Drew Pomeranz for RHP Anderson Espinoza
This one is a strange one. Pomeranz struggled after he was acquired by the Red Sox, then reports came out that the Padres had not disclosed medical information and Boston had the opportunity to undo this trade. Dombrowski opted to keep the trade.
In 2017, Pomeranz was terrific and stepped up in the absence of David Price to help the Red Sox to a second straight AL East title. However, towards the end of the year, Pomeranz velocity dropped vastly and after an injury in 2018 Spring Training he never got back on track.
With 2018 ending, there is pretty much no chance he makes the postseason roster, and we may have seen him throw his last pitch in a Red Sox uniform as he is becoming a free agent after this season.
On the other hand, the Padres likely are not too thrilled with what they have gotten from former top prospect Anderson Espinoza. After throwing 32 innings in class A for the Padres in 2016, he was shut down and sat out almost a year before having Tommy John surgery. Because of this, he has not thrown a pitch since 2016.
Who won this trade?
Both teams are likely pretty unhappy with the outcome of this deal, though it appears the Red Sox won this deal for now. Pomeranz did contribute one great year which helped win the division while Espinoza has been shelved for over two years now. This could change if Espinoza comes back and lives up to the hype he used to have, but that seems unlikely to happen.