Mike Tyson made more than $300m (£187m) and fought 56 times in his 18-year career, but he has now filed for bankruptcy. It is just the latest disturbing development in the life and crimes of sport's most notorious athlete.
Tyson filed for bankruptcy on Friday in New York while speculation about his career was starting to take a series of bizarre twists and turns. He claims he has no money left and people close to him claim that he has no desire to fight which is a fearsome cocktail.
Tyson, 37, has survived two financially disturbing divorces and a catalogue of other chaotic monetary adventures during nearly 20 years as one of the sport's best known anarchic icons.
Last June he was paid $25m for his fight against Lennox Lewis in Memphis. It was a fight that many believed Tyson could win at a time in his career when tales of excessive spending and dwindling bank accounts were rife.
On that balmy night at the Pyramid on the banks of the Mississippi, Tyson was beaten so thoroughly that many doubted he would ever put on a glove again but the awful truth was that he had to keep fighting to somehow match his spending.
Ever since Tyson was a teenage protégé he has been reckless with his cash and an early incident when he was 21 involved giving a transport policeman in New York a brand new Bentley. There are thousands of stories like that ranging from gifts of diamond bracelets worth $200,000 to small personal handouts of $1,000. Many people inside the business of boxing have regularly pointed the finger at Don King - Tyson's major promoter - claiming that the great fight maverick had often paid himself far too much "in fees" for arranging Tyson's fights.
In 1998 King and Tyson had a spectacular fallout and they each initiated legal proceedings for $100m against the other. This case is still working its way slowly and expensively through the American legal system and there was a rumour last year that it was costing Tyson more than $1m per month to keep the charge against King buoyant. Tyson last fought in February of this year when he cleared in excess of $6m for 49 seconds work, but he has a large entourage of well-fed and well-dressed men and women and they all work for Tyson. Therefore, they are all paid for by Tyson and in his world of excessive glitz and glamour nothing is cheap.
Tyson's first wife, the American actress Robin Givens, walked away with a settlement of over $10m and last year his second wife left the divorce court with a promise of $6.5m from the boxer's future earnings.
In between marriages Tyson has been in prison on two occasions sadly with the assistance of some of America's most expensive legal minds. In addition to the prison sentences, one for rape and one for a road rage incident, Tyson has repeatedly had to defend himself against a seemingly endless catalogue of sexual harassment charges. Three years ago it was said that he retained legal representation at a cost of $10,000 each week just in case the police raided his home in Las Vegas one more time.
Perhaps Tyson is best known for his mad spending on things like rare tigers, a snip at a $100,000, and his shopping sprees in the exclusive stores in Las Vegas that often run to more than half a million dollars. I have been on one and the figures are quite staggering.
In 2000 when he fought in Manchester against Julius Francis, Tyson wanted to buy a Formula One racing car and no amount of zeroes would dissuade him from his search. Thankfully, it was pointed out to him that he would never be able to drive the car on the street and that seemed to do the trick, but he settled instead on a watch that cost nearly £1m.
Tyson will still continue with his legal fight against King, but even if he wins there is unlikely to be very much left after the lawyers have had their spoils. Hopefully, he will fight again but unless he has a drastic change in the way he runs his life he will be fighting for nothing which, according to him, is exactly what he has left from his career so far.
Perhaps he will actually do what he said he would do during a BBC documentary in 2000 and pack it all in and go to Africa and devote his life as an aid-worker for nothing.
FIGHTING MAN TYSON'S MILESTONES
1966: Born 30 June in Brooklyn.
1985: Starts professional career with first-round knockout of Hector Mercedes.
1987: Becomes undisputed world heavyweight champion beating IBF title-holder Tony Tucker.
1988: Marries actress Robin Givens, but they divorce the following year.
1991: Charged for rape of Desiree Washington
1992: Convicted on rape and other charges, jailed for six years.
1997: Fined £2m and lost Nevada licence after biting Evander Holyfield's ears.
1998: Sentenced to a year in prison for assault.
1999: Fined £125,000 by the British Boxing Board of Control for striking the referee, John Coyle.
2002: Lewis stops Tyson in the eighth round in Memphis.
2003: 22 Feb - Beats Clifford Etienne with first-round knock-out.
3 Aug - Files for bankruptcy.