Ali, as a young teen I bet 5$ he would beat Smokin Joe that first time. Later i bet a couple dollars with a sucker that he'd "whip" that uknown Norton(opps). Then I was sure Big George would murderize Ali. I bet 60 dollars on Norton in their third(but controversial) match. I was picking up a date and bet her poor kid brother 10 bucks that he'd beat Neon Leon(I felt bad for taking advantage of him til Ali lost).
Matter of fact I lost every bet on a Ali fight over the years. I began to think he'd only lose if I bet on him to win.
But I had my day, it was easy to find people to take him when he fought Holmes. I won about as much as I lost over the years that night. Of course I quit betting on fights after that(kinda).
Not exactly what you were looking for in this thread, but I thought I'd share it with you just the same.