4) Worst Red Sox trade: Sparky Lyle to the Yankees
Any trade involving the Red Sox and New York Yankees is bound to go down in history as a memorable one. On March 22, 1972, the two longtime rivals made a deal that would turn out to be one of the worst the Red Sox could ever make.
Sparky Lyle was a very good reliever for the Red Sox in the late 1960s and into the early 1970s. At 22-17 with a 2.85 ERA out of the bullpen, he was one of the pitchers who helped increase the importance of bullpens. Specifically, he was a founding father of the closer role.
Lyle would turn up the heat immediately upon joining the Yankees. Over the course of seven seasons, Lyle was 57-40 with a 2.41 ERA. He saved 141 games for New York and captured the 1977 American League Cy Young Award.
To land Lyle, the Yankees gave up two players. Danny Carter was an aging first baseman who would hit .262/.301/.384 for the Red Sox in three seasons. He never played more than 100 games for them in any of those years. Mario Guerrero was much less productive. He batted .241/.278/.278 for the Red Sox in his two years. He never once hit a home run in any of his 537 plate appearances.
This is an all-time bad Red Sox trade made even worse by where he ended up.