The worst breakups in Red Sox history
Designated hitter: Reggie Jefferson
In 1996, he batted .347 with 19 homers and would have competed for a batting title with more at-bats. However, he couldnt hit lefties, causing him to be left off the playoff roster in 1999 against the Indians. When given the news, he stormed off, alienating himself from his teammates and essentially ending his career.