7. Bill DeWitt Trades Frank Robinson

Dumbass Move By: Bill DeWitt
Date: 12/9/1965
Being a general manager means going with your gut, which is exactly what DeWitt did when he traded Frank Robinson to the Orioles for two pitchers and a minor league outfielder. DeWitt was under the assumption that Robinson was an "old 30" and past his prime. How did that turn out? The Orioles newest acquisition won the Triple Crown and American League MVP in his first season. The Big Red Machine with Frank Robinson? Wouldn't have been fair.