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Boston Red Sox: Remembering the worst trades in franchise history

By Drew Athans

WASHINGTON, D.C. - 1919: Babe Ruth poses outside the dugout for a photo, before a game in what looks like Griffith Stadium in Washington in 1919. (Photo by Mark Rucker/Transcendental Graphics/Getty Images)
WASHINGTON, D.C. - 1919: Babe Ruth poses outside the dugout for a photo, before a game in what looks like Griffith Stadium in Washington in 1919. (Photo by Mark Rucker/Transcendental Graphics/Getty Images) /
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Bronx, NY – JUNE 12: Infielder Jeff Bagwell #5 of the Houston Astros at bat against the New York Yankees during the interleague game on June 12, 2003 at Yankee Stadium in Bronx, New York. The Yankees defeated the Astros 6-5. (Photo by Al Bello/Getty Images)
Bronx, NY – JUNE 12: Infielder Jeff Bagwell #5 of the Houston Astros at bat against the New York Yankees during the interleague game on June 12, 2003 at Yankee Stadium in Bronx, New York. The Yankees defeated the Astros 6-5. (Photo by Al Bello/Getty Images) /

The Boston Red Sox have made countless shrewd deals over their long and storied history. Here’s a look at some of the worst trades they’ve ever made.

The history of the Boston Red Sox is filled with great players who thrilled the Fenway Faithful with their exploits on the baseball field. Many of the greatest Red Sox legends spent the entirety (or close to it) of their careers in Boston and became legends after their playing days were over.

However, like any franchise that’s been around as long as they have (especially over a hundred years), their history is also littered with great players they traded away. Sometimes these deals worked out, but often they ended up hurting the Red Sox and in many cases, the damage lasted for years.

The list that follows takes a look at what I think are some of the worst trades the Red Sox have made in franchise history. Some of these deals ended up being one-sided in favor of the teams on the other end, and some benefited the Red Sox but still ended up being failures for various other reasons. All impacted the Red Sox negatively to some degree or other.

Presented in (mostly) chronological order, let’s begin!

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