10 worst Boston Red Sox trades in team history

Babe Ruth Red Sox FF Portrait
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A long history with plenty of losing must mean the Boston Red Sox have made some mistakes along the way. Indeed, they have.

Red Sox general managers past and present have made some egregious errors in judgment when it came to trading for players. Sometimes they bought a veteran and gave up a future star. In other instances, the Red Sox gave up a major leaguer for prospects that never did a whole lot.

A mix of legendary and ugly, these are the ten worst trades the Red Sox have ever made.

10) Worst Red Sox trade: Jamie Moyer to the Mariners for Darren Bragg

There’s no bragging about this Red Sox trade despite the presence of the most braggadocious player in MLB history in terms of name being present in it, Darren Bragg. At the 1996 trade deadline, the Red Sox acquired him from the Seattle Mariners for starting pitcher Jamie Moyer.

Bragg was a decent outfielder for the Red Sox in his two and a half seasons with them. In fact, his time in Boston was the peak of his long MLB career as a journeyman outfielder.

Speaking of long MLB careers, Moyer spent parts of 25 seasons in the bigs. He was in the middle of his age 33 season when the Mariners acquired him from the Red Sox. The ultimate late bloomer, Moyer did reach free agency after the season ended but would go on to re-sign with the Mariners and would regularly contend for the Cy Young Award well after Bragg was already gone.

It’s hard to blame the Red Sox for this because who would have expected a sixth place finish from him in 1999, a fourth place in 2001, and a fifth place in 2003. If they had only held onto him for one more season, maybe the Red Sox could have had him in the same rotation with Pedro Martinez.