Jason Bay
You don’t usually consider a trade where you get rid of one of the most feared sluggers in the league, but this trade was still a good one for the Red Sox. After seven incredibly productive and successful seasons in Boston, Manny Ramirez‘ act was wearing thin and grating on his teammates, manager, and fans.
In addition to (allegedly) faking injuries and refusing to play when called upon, the breaking point was reached when Ramirez threw longtime Red Sox traveling secretary Jack McCormick to the floor in anger when he couldn’t get more than the allotted number of game tickets for his family.
The Red Sox promptly shipped Manny out to the Dodgers at the 2008 trade deadline in a three-team deal and in return got Jason Bay from the Pittsburgh Pirates. Bay was the polar opposite to Ramirez in terms of personality, calm and friendly and he immediately became a key contributor.
In 49 regular season games with the Red Sox in 2008, Bay hit .293 with 9 home runs and 37 RBI. He was even better in the postseason, hitting .412 with 2 home runs and 5 RBI in the ALDS and .292 with a homer and 4 RBI in the ALCS. For an encore, he had a fantastic 2009 season hitting .267 with 36 home runs and 119 RBI.
The Red Sox offered him a contract after the season in the hopes of keeping him in Boston long-term, but he instead went to free agency and left for the New York Mets. While Bay was initially thought of as the one that got away, it turns out the Red Sox got the best of him in 2008 and 2009.
He battled injuries and decreased production over his three years in New York before retiring in 2013 after a final season spent in Seattle. Still, his brief time in Boston and his monster 2009 helped Red Sox fans get over losing Manny (who ended up having his own issues with PEDs after leaving Boston).