Jon Lester – First traded to Oakland, Lester would then signed a mega-deal with the Cubs after the 2014 season. The record in Boston was a very impressive 110-63. He pitched two outstanding games in the 2013 World Series and owned a playoff record in Boston of 6-4. There’s no questioning Lester’s postseason record. He doesn’t miss many starts and gives 200+ innings a season. The Red Sox received Cespedes in a mid-season trade for Lester.
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John Lackey – From outcast to hero in Boston when fans became aware he pitched a season with a dead arm. Lackey came back strong in 2013, going 10-13. His record in Boston was 47-43. He posted a 3-1 postseason record with Red Sox. Now Lackey is leading the National League in home runs allowed. He came to Boston as a free agent and was sent to Cards for Joe Kelly and the now released Allen Craig.
Rich Hill – It’s difficult to keep track of how many times Hill pitched for the Red Sox. He signed as a free agent and left as a free agent. In four Boston seasons, Hill was 4-1 with a minuscule 1.34 ERA. Hill signed a free agent deal with the Dodgers, where he does well provided he avoids blisters.
Rubby De La Rosa – Arrived in Boston via the Punto deal with the Dodgers and left via trade to Arizona. With the D-Backs, Rubby went 14-9 and looked like he had finally started to turn the pitching corner, but injuries set him back. He was terrible with Red Sox, posting a 4-10 record and 4.54 ERA.
Wade Miley – The good news is Miley is an “Inning Eater.” The bad news is generally what happens in those innings. He was traded from Arizona to Boston for Allen Webster and De La Rosa, then shipped to Seattle after one season for Carson Smith. In his one season in Boston Miley was 11-11 with a 4.46 ERA. Now he’s a member of that dreadful Baltimore staff.