#19. Anthony Young Loses 27 Consecutive Games
Biggest loser ever? Yes. Anthony Young lost a record-breaking 27 games in a row from May 6, 1992 to July 24, 1993. He broke the shitty streak against the expansion Florida Marlins. If at first you don't succeed, try try again...but maybe in AY's case a good ol' fashioned quit was called for.