23. Tom Hicks and George Gillett – Liverpool
Looking at Liverpool now, it’s insane to imagine that the club almost went out of business under these two pantomime villains. Texans Hicks and Gillett bought the Reds promising a new stadium and major investment. To sum up, neither of these things happened, and it all went downhill rapidly.

Soon everybody was at loggerheads with each other. Fans labeled the pair as asset strippers and it all escalated into a major court case that saw them lose control of the club. They left Liverpool in the relegation zone with no trophies after three years in charge as the definition of terrible owners.