Jason Varitek and Derek Lowe
This one is a twofer and might be one of the biggest swindles the Red Sox have ever pulled off in their 100-plus year history. In one fell swoop they sent out a decent reliever and received two players who were instrumental in helping them end eighty-four years of futility and finally win the World Series.
Heathcliff Slocumb was a pretty good reliever for the Red Sox, saving 31 games in 1996 and 17 in 1997 when he was traded to the Seattle Mariners for Jason Varitek and Derek Lowe. Seattle was desperate for relief pitching as they made their postseason push and parted with their two players.
Lowe had only appeared in twelve career games and Varitek was still in the minor leagues when they arrived in Boston. While Slocumb did help Seattle make the postseason in 1997 before his career fizzled out (he was out of baseball by 2000), Varitek and Lowe became cornerstones of the 2004 World Series champions.
Lowe spent his eight seasons in Boston in the same way as Tim Wakefield, bouncing between the rotation and the bullpen. He won 21 games as a starter in 2002 and 17 the following year. For his Red Sox career (1997-2004), he compiled a 70-55 record (111 starts in 384 appearances) with 85 saves, a 3.57 ERA, and 673 strikeouts.
For good measure, Lowe was the winner in all three clinching games in 2004: Game Three of the ALDS, Game Seven of the ALCS, and Game Four of the World Series. He left after the season in free agency with his Red Sox legacy secure.
As for Varitek, he became the Red Sox regular catcher in 1998 and spent his entire career in Boston before retiring after the 2011 season. He was the team captain from 2005-2011 and helped them win the World Series in 2004 and 2007. He put up a career .256 batting average to go along with 193 home runs and 757 RBI. He also caught four no-hitters, which is a league record.
This trade is often pointed to as being one of the most lopsided not just in Mariners history, but in baseball history. It’s hard not to argue that it’s also one of the best in Red Sox history.