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As one of the best pure hitters in recent history and a tremendous free agent signing by the Red Sox in 2000, my inclusion of Manny Ramirez to this list may seem a bit odd to the average fan, but the reality is that Ramirez was an embarrassment to himself and his team on numerous occasions.
Throughout his tenure in Boston and his career after, Ramirez provided embarrassments on and off the field, most notably in being caught for performance enhancing drug use on two separate occasions.
Both of those incidents came after his time with the Red Sox came to a close, but given his inclusion on the notorious Mitchell Report, it's likely that Ramirez had used PEDs at some point or another when he was playing in Boston.
As a member of the Red Sox, Ramirez never failed to provide an embarrassment or two each season, either in his failure to play even adequate defense in left field at times, or in his antics that inevitably led to the label of "Manny being Manny."
Not known for his speed on the base paths, Ramirez had a penchant for chucking his batting helmet off his head while charging around the bases trying to score, in an futile attempt to run a bit faster.
One of the funniest and most embarrassing moments in Ramirez's time with the Red Sox came in 2004 when he cut off a Johnny Damon throw from center field while diving to the ground, rolling around a bit before trying to make his own throw to the infield, allowing Orioles outfielder David Newhan to speed around the bases for an inside the park home run.
In spite of all the craziness that Ramirez brought to the ballpark every day, his embarrassing moments as a member of the Red Sox were humorous failures on the field more often than not. That lands him a spot on the list, but he's not the worst in that regard by any means.