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AnthonyEvery move that Gene Mauch made in the 9th inning of game 5 of the '86 AL playoffs. Cost the game, the series, the pennant, and ultimately (and somewhat indirectly) the lives of Donnie Moore and his wife.
Not that this was unique for Gene, as he also threw away the '64 pennant by overpitching Short and Bunning. At least when he managed Montreal they never got close enough to first to allow him to ruin their chance at a pennant.
My vote for worst manager of the latter part of the 20th Century.