George W. Bush

Team: Texas Rangers
Years of Ownership: 1989-1998
Championships Won and Playoff Appearances: Zero championships / Two playoff appearances

Only fitting that Dubya would own a piece of the Texas Rangers, hell, he is a Ranger. Nearly a decade of ownership ended with Bush being the first Texas governor to be elected to consecutive four-year terms, the Rangers winning their second divisional title in team history, and GWB collecting $14.9 million for his initial purchase. #stunt101