Who is the worst GM is pro sports history?

[Bremen]

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yeah seriously. the phillies and red sox had awful streaks through their history where not only were they bad, they were bad every year for a decade.

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Its hard to compare GMs now and then since FA really changed how the game works. Some teams (such as the Phillies) routinely sold their good players for operating cash. That would be unimaginable today. Could you imagine the Twins dealing Santana for cash so the owner could finance a movie???