In no particular order the two worst GM in pro sports are:
Matt Millen
The Detroit Lions are 24-72 since he took over in 2001.
The year before the Lions were 9-7, and last year they finished 3-13. He is the reason for the "Fire Millen" movement, and must have some type of un-imageable dirt on Ford Family to still be in his position. Some of his resume highlights include drafting Charles Rodgers, Mike Williams, signing Corey Bradford for 7 million, and drafting wide recievers every year. But above all, his winning percentage is .250.

David Littlefield
The Pirates are 422-563 since he took over in July of 2001.
His greatest moves (jokes) where the ones he didn't even get done. Paul Maholm for Alex Rios, and falling in the Ryan Howard for Kip Wells deal. His resume of sucessful trades include. Jason Schmidt, Aramis Ramirez, and Chris Young for no one. His big moves last year were Jeromy Burnitz, and Joe Randa, both now retired. He always will pass up the best player on the draft board and the current Pirates team is last in the NL. He is 141 games under .500 and his farm system empty.
Well done guys, well done.
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