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There is one professional baseball organization that stands out as the worst over the last 20 years. That organization is the Pittsburgh Pirates. They have endured 19 losing seasons in a row. They have played bad baseball and made questionable trades for many years. Their losing performance is illustrative of a team going in the wrong direction.
The Pirates have not always been so bad. They have a history of World Series championships and some of the best baseball players have played for them. But for the last 19 years, they have been the worst team in baseball.
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