One of the greatest running backs of all time, O.J. Simpson has had such a decline that he is arguably more recognisable as a criminal than a football player.
After avoiding jail time for the deaths of Nicole Simpson and Ronald Goldman, Simpson had multiple legal troubles involving taxes, drug trafficking and stealing cable TV.
In September 2007, struggling to pay his debts, Simpson entered the Palace Station Hotel Casino in Las Vegas with a group of men, taking sports memorabilia at gunpoint. When questioned, Simpson attested that the items had been stolen from him.
At the trial, Simpson was convicted of multiple felonies that included kidnapping, robbery, assault and using a deadly weapon. He was sentenced to 33 years in prison, 13 years to the day that he was acquitted of murder.
For some reason, I've never considered this to be the saddest moment of Simpson's life. To me, that will always be when he sold his Heisman to pay part of a court judgement. The embodiment of his youthful promise was auctioned off in an attempt to rectify his idiocy as an adult.