2. Al Davis
TEAM (YEAR PURCHASED): Oakland Raiders (1966)
W-L (WINNING PCT): 381-283-8 (.567)
COMPLEX SAYS: This dude. It was all good for the Cryptkeeper Al a few decades ago when the Raiders won three Super Bowls in a seven-year period. The only thing that has stayed the same since then has been homie's wardrobe and his old school ways. Since 2003, the Raiders have had seven losing seasons and six different head coaches. Plus there's been his epic news conferences where he publicly bashes former head coaches and has been known break out the overhead projector. Commitment to failure? You already know.