Team: Cleveland Indians
Years Of Ownership: 1946-1990s
Championships Won and Playoff Appearances : One championship (1948) / Five playoff appearances

Bob Hope grew up in Cleveland, and after making it big he decided to invest in his hometown Indians in 1946. Hope remained an owner for most of the rest of his life and even saw the Indians win a ring in 1948. His dedication and loyalty was recognized when he made it onto the cover of Sports Illustrated in 1963.