Mike Tyson’s bizarre message of support for Diddy as rapper is denied bail

Mike Tyson wished Sean ‘Diddy’ Combs the ‘best’ just minutes 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 was grilled about his links to Combs, 54, who will stand trial in May 2025.

Tyson, who has known Combs for decades, appeared shocked when made aware of the speculation around his name in the wake of the rapper’s arrest for a host of sex trafficking and racketeering offences last month.

‘Wait I’m synonymous with Diddy? Well, that’s cool,’ he said. ‘I never knew that.’

Asked if he had anything to say, he replied: ‘I wish him the best. In life, I wish him the best.’

Mike Tyson wished Sean ‘ Diddy ‘ Combs the ‘best’ just minutes 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 was grilled about his links to Combs, 54 (pictured together at a Cannes Film Festival party)

Combs has been locked behind bars since he was arrested and charged with racketeering conspiracy, sex trafficking and transportation to engage in prostitution on September 16.

Since then upwards of 120 victims have come forward, but Combs maintains his innocence.

He appeared in court on Thursday, surrounded by his family, where his request for bail was denied for a third time.

A judge offered a May 5, 2025 trial date at the request of his high-powered legal team.

Prosecutors said they estimate their case will take about three weeks, while Combs’ lawyers say they will need about a week to make their case.

Following Combs’ arrest, videos have emerged of the Bad Boy Record founder allegedly acting inappropriately with other celebrities – one such video from 1998 features Tyson.

Combs and Tyson are seen joking around on a couch during an interview with Damon Wayans.

While talking about a time that he fell on stage, Combs puts his hand next to Tyson’s leg.

‘I wish him the best,’ he said of the record label mogul. ‘In life, I wish him the best’

Tyson, who has known Combs for decades, appeared shocked when made aware of the speculation around his name in the wake of the rapper’s arrest (pictured together in 2017)

Tyson grabs Combs’ hand and points out his fancy watch in what has been interpreted as an apparent attempt to de-escalate the situation.

‘He truly is about the Benjamins we see,’ Tyson says.

The former heavyweight champion of the world has been pictured with Combs at multiple events over the years, with the pair partying together at the Cannes Film Festival in 2008 and enjoying a boxing match at Madison Square Garden in 2004.

They also 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 ‘awesome’ and jokingly referred to him as ‘Sugar Diddy.’

‘I just know him for a long time,’ he told PBD Podcast host Patrick Bet-David. ‘I knew him before he was Diddy and for a long time. When I first became champ I knew him.

‘I remember him he used to have crates when he’s at my after parties and stuff. Also when they were throwing parties.’

Bet-David said: ‘So many people in music and Hollywood feared this guy “Diddy”, as if he’s untouchable.’

Tyson replied: ‘Oh sugar Diddy.’

Combs appeared in court on Thursday, surrounded by his family (pictured), where his request for bail was denied for a third time

The rapper was denied bail for a third time, with a judge offering a May 5, 2025 trial date at the request of his high-powered legal team

Tyson’s recent comments were a far cry from Kevin Hart, who tried to disassociate himself from the disgraced music mogul when questioned by DailyMail.com last month.

The comedian, 45, was asked if he recalls seeing any of the now infamous bottles of baby oil found at Combs’s home when he had ‘hosted parties’ for the Bad Boy founder.

‘When I hosted for Diddy? You’re asking the wrong person the wrong question,’ he hit back.

When pressed on whether Combs would be safe in jail, Hart again tried to deflect.

‘Wrong person, wrong question,’ he retorted before heading to dinner with his bodyguard and wife Eniko Hart, 40.

Tyson, nicknamed ‘The Baddest Man On The Planet,’ was the undisputed world heavyweight boxing champion 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, just one year after his release, he bit rival Evander Holyfield on both ears. He was disqualified and temporarily suspended from boxing.

Tyson’s recent comments were a far cry from Kevin Hart, who tried to disassociate himself from Combs when questioned by DailyMail.com last month

In divorce papers, his ex-wife, actress Robin Givens, claimed that their late-1980s marriage was characterized by ‘unprovoked rages of violence and destruction.’

Tyson declared bankruptcy in 2003 and retired from professional boxing in 2006.

He has since appeared on TV shows Entourage and Brothers, and had a cameo in the hit 2009 comedy movie The Hangover.

He is currently gearing up to fight Jake Paul, four months later than scheduled after he was forced to pull out due to an ulcer.

‘Iron Mike’ was initially set to fight Paul on July 20, but experienced a health issue on a flight from Los Angeles to Miami that forced him to push back the highly-anticipated bout.

‘I was doing too much bad food and stuff, and I got sick,’ he told DailyMail.com.

Last month Paul said he would give Tyson $5million more if he lasted more than four rounds – but said the former undisputed heavyweight champion of the world would have to get ‘I love Jake Paul’ tattooed on him if he was unable to reach that mark.