1. Bill Buckner
This play will forever go down as the most infamous error in World Series history. Though the Boston Red Sox eventually shook The Curse of The Bambino in 2004, the severity of the situation in 1986, compounded by the fact it was the Red Sox, who at the time had not won the Series since 1918, had taken the lead in the top of the 10th inning. Skipper John Mcnamara chose to let Buckner stay on the field for the bottom of the 10th instead of making a defensive replacement.
It’s one thing to lose, but for the ball to literally scrape through the legs on a seemingly easy out, it was misery for Red Sox fans.