In 2003 the former World Heavyweight champion declared bankruptcy, despite having received more than $30 million for several of his fights and $300 million during his career.
The years since have been a mixed bag, substance abuse, the death of a child, and more, but Tyson's honesty has gone some way to repairing his reputation.
The 46-year-old said of his current status: "A gentleman who started off on the wrong side of the street and he built his way up and destroyed himself and tore himself down and he built himself up and down and at the end of the day he made it." So "Iron Mike" or the "Baddest Man on the Planet"?.
It would appear that New Zealand's immigration authorities had a great deal of difficulty deciding which when a promoter invited Tyson to bring his one-man show to Auckland next month.
At first he was worthy of a visa, despite the fact that this country does not grant visas to persons with convictions that require more than five years imprisonment. "Special dispensation" was the official spiel.
But when Prime Minister John Key criticised the decision, the writing was on the wall.
And as quick as Tyson's right hook once was, his visa was revoked yesterday by Associate Immigration Minister Kate Wilkinson, who described the original decision as a "finely balanced call".
Revocation was made easier by the withdrawal of support for the visit by the Life Education Trust, which would have been a beneficiary of the visit.
From the wrong side of the tracks, even at 46 and sober, Iron Mike was just too hot to handle for New Zealand, even for the 20 hours he would have been here.
Whether you take the view of promoter Max Markson that "he's a reformed character", an example of how a man "can turn his life around". Or that of Rape Prevention Education executive director Kim McGregor, who said: "We can't have one rule for one and another rule for another."
You would surely like to think that Immigration authorities would have handled a decision on a world-famous personality with more care than basing decision-making on a letter of support, or not, from a charity.