Jeff Bagwell
This one is routinely pointed to as one of the worst trades in Red Sox history by fans and the media alike and for good reason. Jeff Bagwell went on to become one of the most prolific sluggers of his generation and ended up in Cooperstown after his career was finished. His career is always pointed to by Red Sox fans as what might have been.
Bagwell was born in Boston, raised in Connecticut, and grew up a Red Sox fan. He was drafted by the Red Sox in 1989 and was an up and coming player in their minor league system when he was traded to the Houston Astros. The Red Sox were in the midst of trying to win the AL East and make the postseason in 1990 and needed relief pitching.
They approached the Astros about Larry Andersen and in return were asked for Bagwell. Since he hadn’t hit too many home runs thus far in his career, they made the deal and came out on the wrong end of it. Andersen pitched decently for the one month he was on the Red Sox, but they were swept by the powerhouse Oakland A’s in the 1990 ALCS.
Andersen was a free agent at the end of the season and left for San Diego. Meanwhile, Bagwell spent his entire career in Houston, from 1991 to 2005 and ended his career with a .297 average, 449 home runs, 1529 RBI, an OBP of .408, a .948 OPS, 1517 R, and 1401 BB. He was inducted into the Baseball Hall of Fame in 2017.
In essence, the Red Sox traded Jeff Bagwell for one month of Larry Andersen, who appeared in 15 games with a 1.23 ERA and one save in 22 innings. Granted, it may not have been obvious that Bagwell was a future Hall of Famer, but he was a rising star in the farm system and was traded away for a month of a then-37-year-old reliever.
If this isn’t the worst trade the Red Sox have ever made, it’s close to it.