I would say Muhammad Ali fits this discription perfectly. He ended his career as the most famous man on the planet, he had wealth and luxury, but he suffered two devastating losses in a row. THe first one and the most devastating by his former sparring partner from 71-74, "The Easton Assasin" Larry Holmes. Holmes was the only person to ever KO/TKO Ali. Holmes beat the heck out of Ali, and in the end layed off the attack a little bit and just jabed with the occasional right or left hook. Ali was finished in round 11 and then couldn't get up for the 12th round. Trevor Berbick won a 15 round decision of ALi, but it was very lop sided. Like Holmes Berbick showed mercy and respect to Ali in the end so Ali wouldn't be completely devastated. If you can think of anyone else that retired in the same shoes as Ali than please tell us about him.