22. Chelsea Doesn't Get Their Money's Worth For Shevchenko

Dumbass Move By: Roman Abramovich and Chelsea
: Summer 2006
A favorite player of Chelsea owner Roman Abramovich, Andriy Shevchenko was transferred from A.C. Milan for €44 million, or $58.66 million. In only 48 games (and three years) with Chelsea, Shevchenko scored a meager nine goals. And it wasn't that he turned into a bust because later on in his career with FC Dynamo Kyiv, he scored 21 goals in almost the same number of appearances. Failing to rise to the occasion? Think they got a pill for that. Pause.