Sonny Liston, his hero, died broke and broken-down.
Still, Mike Tyson might be the only one who doesn't see where this is headed.
And he is already halfway there.
News over the weekend that Tyson filed for bankruptcy despite grossing an estimated $300 million during his boxing career hardly qualified as news. The figure, though, is substantial enough that the first time people try to get their minds around it, they assume Tyson got the worst financial advice in history.
But that would be denying Don King his due. For all his exotic pets and more exotic bedspreads, Tyson needed help to go through that much money that fast, which is why he is suing his former promoter.
The fighter contends King stole at least a third of that total, yet so twisted is their relationship that $100 million wouldn't barely cover the cost of therapy if Tyson ever did manage a permanent break. Betrayal has been the one constant in Iron Mike's life and nobody does that better than King.
When Tyson walked out of a jail cell eight years ago and right back into King's arms, much of the boxing world gasped. Rival promoter Lou Duva only shrugged.
"Why would anyone expect Mike to come out smarter?" Duva said. "He went to prison for three years, not Princeton."
Yet his cronies insisted the Tyson who walked out of the Indiana Youth Center in March 1995 was a changed man. He had those impressive tattoos of Mao and Arthur Ashe on his arms and a stack of weighty books under them.
The only real changes were these: The Tyson who came out was three years older and a much more desperate man. That's because he was nowhere near the warrior, mentally and physically, who began the stint as a guest of the state after his conviction on a rape charge.
Tyson must have known that in his heart of hearts the day he was set free. Maybe that's why he rushed back to King, why he went along with the charade. An ex-con with limited education, job experience and only one marketable skill, after all, wasn't likely to find such profitable work working for anyone else.
But Tyson also knew knocking down the stiffs King kept parading in front of him would only keep the public content for so long. It all started to go wrong with the first loss to Evander Holyfield in November 1996. On the eve of the rematch, King invited a few writers over to his Las Vegas home.
There, brooding and introspective, Tyson talked about his fascination with Liston's sad life and tragic death. Maybe because from where he sat, Tyson, once the youngest heavyweight champion ever and now 37, could see his own end in sight.
Ever since Cus D'Amato plucked Tyson out of a Brooklyn ghetto in his late teens and set him down in a Catskills gym to learn the racket, the fighter would sit in the dark by himself and watch black-and-white films of all the heavyweight champions. He loved the lore and the way all of them lived - large. He craved the respect they commanded. He especially loved dark stories like Liston's; to Tyson they were life-affirming, in a tortured kind of way.
But those stories sound much better in the retelling than they do the first time around. Tyson's misery isn't ending, it's only going to become more expensive. Shopping is one of the few things that always made him feel good, but just as the bankruptcy filing proves he hasn't curbed his appetite, it's clear he can't hold his own in a ring against a half-decent heavyweight anymore.
But he can't afford to stay out of the ring for long, either. Tyson will never command $30 million for an evening's work again and a rematch with Lennox Lewis, a third go-round with Holyfield or a first with Roy Jones Jr. - all potential big paydays - already have exceeded his reach.
More likely are opportunities against rising stars looking for a fighter with a name that will look good on the "W" side of their ledger. All that time Tyson claims to have spent readying the great books and religions of the world will not be in vain. If he stays in the fight racket, he's about to learn a lot about pain and humility, to add broken-down to broke.
Like Liston at the end, his pockets are turned inside out and you wonder whether Tyson knows what the vultures circling overhead know: that he is closer to the end of his useful days than the beginning.