Mike Tyson wished Sean' DD Combs the best moments before the disgraced rap mogul was denied bail for a third time.
In an exclusive interview with DailyMail.com, the 58-year-old boxing legend opened up about his relationship with Combs, 54, who is due to go on trial in May 2025.
Tyson, who has known Combs for decades, was shocked to learn of the speculation surrounding her name following the rapper's arrest last month on sex trafficking and racketeering charges.
'Wait am I DD's equivalent? Well, that's great,' he said. 'I don't know that.'
Asked if he had anything to say, he replied: 'I wish him well. I wish him the best in life'' he said.
Mike Tyson wishes Sean 'DD' Combs 'the best' minutes before disgraced rap mogul is denied bail for third time
In an exclusive interview with DailyMail.com, the 58-year-old boxing legend and Combs, 54 (pictured together at a Cannes Film Festival party)
Combs has been behind bars since he was arrested on September 16 and charged with racketeering conspiracy, sex trafficking and transportation to commit prostitution.
More than 120 victims have since come forward, but Combs maintains his innocence.
He appeared in court on Thursday, surrounded by his family, where his bail request was rejected for the third time.
A judge granted a hearing date of May 5, 2025 on the request of his high-powered legal team.
Prosecutors estimate their case will take about three weeks, while Combs' attorneys say they will need a week to present their case.
Following Combs' arrest, videos surfaced of the Bad Boy Records founder allegedly engaging in inappropriate behavior with other celebrities — one such video of Tyson in 1998.
Combs and Tyson can be seen joking around on a couch during an interview with Damon Wayans.
Speaking about the time he fell on stage, Combs put his hand next to Tyson's leg.
'I wish him well,' he said of the record label mogul. 'In life, I wish him the best'
Tyson, who has known Combs for decades, was shocked to learn of the speculation surrounding the rapper's name after his arrest (pictured together in 2017).
Tyson grabs Combs' arm and points to his fancy watch, which is interpreted as an obvious attempt to escalate the situation.
“He's really about the Benjamins we see,” Tyson says.
The former heavyweight champion of the world has teamed up with Combs at several events over the years, including partying at the 2008 Cannes Film Festival and enjoying a boxing match at Madison Square Garden in 2004.
They sat together to watch the super welterweight boxing match between Floyd Mayweather Jr. and Conor McGregor in August 2017 in Las Vegas, Nevada.
Tyson opened up about their friendship in an interview last year, in which he described Combs as 'amazing' and jokingly referred to her as 'Sugar DD'.
'I've known him for a long time,' she told PBD podcast host Patrick Bett-David. “I knew him before he was TD and for a long time. I knew him when I first became a champion.
'I remember him having boxes when he was at my parties and stuff. When they feast.'
Bet-David said: 'A lot of people in music and Hollywood were scared of this guy as “DD”, like he was untouchable.'
Tyson replied: 'Oh sugar DD.'
Combs appeared in court on Thursday, surrounded by his family (pictured) as his request for bail was rejected for the third time.
The rapper was denied bail for the third time, with the judge granting a hearing date of May 5, 2025 at the request of his high-powered legal team.
Tyson's latest comments were a far cry from Kevin Hart, who tried to distance himself from the disgraced music mogul when questioned by DailyMail.com last month.
The 45-year-old comedian was asked if he remembers seeing any of the now-infamous baby oil bottles at Combs' house when he hosted 'parties' for the Bad Boy founder.
'When I hosted Titti? You are asking the wrong question of the wrong person,” he retorted.
When pressed on whether Combs would be safe in prison, Hart tried to deflect again.
'Wrong person, wrong question,' he replied before heading out to dinner with his bodyguard and wife Eniko Hart, 40.
Nicknamed 'The Baddest Man on the Planet', Tyson was the undisputed heavyweight boxing champion of the world in the 1980s.
But his career was overshadowed by his controversies.
In 1992, he was convicted of raping teenage beauty queen Desiree Washington in Indiana and served three years in prison.
In 1997, a year after his release, he bit rival Evander Holyfield in both ears. He was disqualified and temporarily suspended from boxing.
Tyson's latest comments were a far cry from Kevin Hart, who tried to distance himself from Combs when questioned by DailyMail.com last month.
In divorce papers, his ex-wife, actress Robin Givens, said their marriage in the late 1980s was characterized by 'unprovoked violence and destruction'.
Tyson declared bankruptcy in 2003 and retired from professional boxing in 2006.
He later appeared in the television shows Entourage and Brothers, and had a cameo in the 2009 hit comedy film The Hangover.
He is currently preparing to fight Jake Ball, four months after he was forced to withdraw due to an ulcer.
'Iron Mike' was initially scheduled to fight Paul on July 20, but suffered a health problem on the flight from Los Angeles to Miami that pushed him back from the highly anticipated bout.
'I was doing really bad food and stuff and I got sick,' she told DailyMail.com.
Last month Paul Tyson said he would pay $5 million if he lasted more than four rounds – but the former undisputed heavyweight champion of the world said he would have to get an 'I love Jack Paul' tattoo if he couldn't reach that goal. .
