Iron Mike was undoubtedly on a downward spiral in 2003 when he stepped into the ring on February 22 in Memphis.
He faced fringe contender Clifford Etienne and knocked him out in just 49 seconds – despite claiming he had a broken back.
The pre-fight was marred by rumours of the then 36-year-old’s fitness with allegations that he sacked off his training camp in order to party in Las Vegas.
And he even took time out to get his now iconic facial tattoo just a week before the bout.
Despite all of that, and “The Baddest Man on the Planet” cancelling the fight before changing his mind, the legend still claimed what would be his final ever victory between the ropes.
He filed for bankruptcy soon afterwards but the American has since gone on to bounce back with his highly-profitable cannabis farm, several Hollywood movie appearances and his comeback to the ring against Roy Jones Jr in 2020.
But while he has rebuilt his life, his opponent that night also hit rock bottom but now has a new passion since being JAILED.
Etienne, now 53, is serving a 105-year prison sentence in Louisiana for armed robbery, kidnapping, and attempted murder of a police officer after being convicted in 2006.
The ex-heavyweight, who retired with a record of 29 wins, two draws and four losses, discovered a love of painting while in the joint.
Lynn O’Shea handles Etienne’s business affairs and she revealed to TMZ how art has saved his life behind bars.
She said: “He’s amazing. He took painting serious inside and after he earned trustee status he was actually able to become the warden’s artist and sleep in his paint room.
“That kept him away from all the drama in gen pop.
“The city of New Orleans bought one that hangs in a district police department, if you can believe that.”
However, life has not always been a pretty picture for the artist on the inside.
Back in 2015 he was transferred to a new prison after he was attacked and nearly killed in in his paint room.
O’Shea added: “Things slowed down after the attack. He used to make all his own canvas and stuff to paint on … but now he’s locked down.
“I’m hoping some friends from his past life as a boxer can help him out.”