Season 2: #4 Leroy Caldwell

At 73 years of age, Leroy Caldwell can be found in the City Boxing Gym in Las Vegas waiting for the break he never had as a fighter.

He fought the best heavyweights of the 1970s and 1980s and caused a few upsets. He's been to prison, he's been screwed and now he's trying to claim a debt he feels boxing owes him for services rendered.

He sparred the likes of Muhammad Ali, Bob Foster and Sonny Liston and fought Cleveland Williams, Oscar Bonavena, George Foreman, Earnie Shavers, Ron Lyle, Pinklon Thomas and countless others.

He also worked as a bouncer in Las Vegas nightspots, let an underage Mike Tyson in to one place, and he talks about life on the road as a heavyweight outsider.

At 73 years of age, Leroy Caldwell can be found in the City Boxing Gym in Las Vegas waiting for the break he never had as a fighter. He fought the best heavyweights of the 1970s and 1980s and caused a few upsets. He's been to prison, he's been screwed and now he's trying to claim a debt he feels boxing owes him for services rendered. He sparred the likes of Muhammad Ali, Bob Foster and Sonny Liston and fought Cleveland Williams, Oscar Bonavena, George Foreman, Earnie Shavers, Ron Lyle, Pinklon Thomas and countless others. He also worked as a bouncer in Las Vegas nightspots, let an underage Mike Tyson in to one place, and he talks about life on the road as a heavyweight outsider.