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The Red Sox might need their own thread.
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Thanks for reminding me.
In my lifetime (born 1982), I'd have to say Game 6 of the 1986 World Series followed by Game 7 of the 2003 ALCS.
Game 6 of the '86 World Series is probably the toughest loss in franchise history as well. One strike away from a World Series Championship...how can it get worse than that?