MIKE TYSON was known for making plenty of enemies in a brutal heavyweight career that saw him labelled The Baddest Man on the Planet.But that career also saw him make a multi-billion dollar circle of friends – from fellow athletes to former rivals, Hollywood A-listers and even a US President.Mike Tyson is making his return to the ring against Jake PaulCredit: SportsfileTyson (pictured with Conor McGregor) has a long list of celebrity buddiesIron Mike has been back in boxing with a number of exhibitions over the years, but now he’s stepping things up against Jake Paul.The bout against a YouTuber 31 years his junior will be his first officially sanctioned fight since 2005.In his prime, the likes of Arnold Schwarzenegger, Will Smith, Madonna, Pamela Anderson, Donald Trump and Jack Nicholson could all be spotted ringside at Tyson’s fights.Here’s the rundown of the boxer’s all-star cast of celebrity BFFs.READ MORE ON MIKE TYSONDonald TrumpMike Tyson and the US President-elect go back many years.Trump was even among the guests at Tyson’s manic 30th birthday party.In his book ‘Undisputed Truth’, Tyson wrote of “spending a fortune flying in friends from all over the country and putting them all up in a nearby hotel”.They could not stay in his house because the 19 bedrooms were reserved for all the “lady suitors” he planned on bedding.Most read in BoxingCASINO SPECIAL – BEST CASINO WELCOME OFFERSTyson wrote: “We had 13 different chefs, each one cooking in their own kitchen.”Everyone from Oprah to Donald Trump to Jay-Z to street pimps and their hos were there. There was a guy hand-rolling cigars.”You entered the house on an actual red carpet – once you got past the 40 big Fruit of Islam bodyguards stationed outside.Mike Tyson gives Tennis star Serena Williams a boxing lesson “I was so egomaniacal that I reserved the 19 bedrooms in my house for girls who I wanted to sleep with.”I told Crocodile, ‘see all these girls? They’re mine’.”And the boxer endorsed Trump in both the 2016 and 2024 elections.He told the Huffington Post in 2016: “He should be president of the United States. Hell yeah, big time!”Counting down to Jake Paul vs Mike Tyson…READ MORE on all the build-up to the massive clash in Texas on Netflix…All the info:Latest news and features: And this year, he went into more detail on the IT IS WHAT IT IS podcast, saying: “Trump is going to win. “Yeah, it’d be nice if he wins, yeah. I have my reasons [for wanting him to win]… He is just a good man. Listen, I don’t agree with all his s***.”Nobody agrees with all my s***, but you know, they [are] good people. “No one is perfect in this world. Everybody got their s***, you know.”Mike Tyson and Donald Trump at a March of Dimes dinner in New York in 1989Credit: GettyTyson (back left), Kid Rock (second to back left) and Dana White (front right) endorsed Donald Trump for PresidentCredit: Instagram / @danawhite via ifltvboxingDana WhiteMike Tyson and Dana White have a mutual friend in President-elect Trump, who they are both supporters of.But Tyson has also been very supportive of the UFC boss’ increasing involvement in boxing and said he expects White to get better fights arranged.He said: “That’s going to be the best thing to happen to boxing just like UFC.”If you’re in UFC and if anybody’s booing the fight, you’re not going to see that guy. His next fight is going to be in South Dakota somewhere. Only good fights.”If you don’t have a good fight, you ain’t never going to see that guy again. Not like boxing. “‘This guy’s going to fight next month again? We don’t want to see that.’ “If any fights stink, you’re not back in the UFC no more. You’re never going to see those guys again.”Mike Tyson with Dana White on the Hotboxin’ podcast in 2021Credit: YouTube: Hotboxin’ with Mike TysonTyson with Dana White at UFC 160Credit: Getty – ContributorNovak DjokovicMike Tyson is a huge tennis fan with his daughter Milan a keen player of the sport, which he claims has changed his life.And the boxer has revealed his favourite player is Novak Djokovic.He said: “Novak Djokovic is my favourite at the moment. If he is OK, I really like to watch him.“He is my favourite because the way he has come back from injury and beaten guys like [Rafael] Nadal and [Roger] Federer is amazing. He is a true fighter.”The pair exchanged handshakes and took pictures at Indian Wells and Tyson is keen to attend the Serb’s matches whenever he can.Mike Tyson has called Novak Djokovic his favourite playerCredit: GettyTyson watching the French Open with daughter Milan to the left and Kylian Mbappe in frontCredit: AFPSerena WilliamsThe 23-time Grand Slam winner is Tyson’s 15-year-old daughter Milan’s favourite player.In a picture in 2016 with Serena and Milan he wrote: “Milan on the right and of course the great Serena Williams. “Milan is serious about tennis and is very fortunate to get to spend precious moments Serena. Thank’s Serena.”And the American, known for her power on the tennis court, linked up with Iron Mike to put in a brutal display with the pads.Tyson wrote on Instagram that Williams “has some power”.And he added: “I don’t want to get in the ring with this GOAT @Serena Williams, much love and respect.”Serena Williams is Mike Tyson’s daughter’s favourite player and the former heavyweight champ taught the tennis star some boxing movesCredit: serenawilliams/instagramIron Mike said he ‘wouldn’t want to get in the ring with her’Credit: serenawilliams/instagramMike Tyson with daughter Milan on the right meeting Serena WilliamsCredit: InstagramArnold SchwarzeneggerFollowing his ringside appearances, Tyson maintained his friendship with the Terminator star turned governor of California.In 2021, he was invited to Schwarzenegger’s LA mansion where the pair played chess and mini-golf together.UFC star Henry Cejudo, who joined the duo, captioned his pictures “Legends only”.Schwarzenegger was often ringside at Tyson’s fights and the boxer visited his home in 2021Credit: Instagram / @henry_cejudoMike Tyson enjoying a round of mini-golf at the Schwarzenegger homeCredit: Instagram / @henry_cejudoTupacMike Tyson and Tupac were close friends with the rapper even coming to visit him in prison.The boxing icon said: “I talked to him as a young, shy kid. I went to prison, he wrote me a letter and came to see me.”That’s how we became friends, we talked on the phone and built a relationship I said to him, ‘When I leave you’ll be coming in’. “We were always saying when we came out of prison we would conquer the world, everyone would know our names that’s what happened. But, you know [how the rest went].”And he said that he was even meant to meet Tupac on the night he was shot.Tyson commented: “I was at home. I was supposed to meet with him, then I heard the news. I was supposed to join those guys, I wanted to hang out with them.”He would then never see his pal again before he died as “they wouldn’t let anyone see him” while he was in hospital.He continued: “I was home, I was in my house when I found out he had died as well. I was like everyone else, it was so overwhelming, we lost somebody special.”Mike Tyson and Tupac were close friendsCredit: GettyThe rap legend even came to visit him in prisonCredit: InstagramOprah WinfreyMike Tyson remains friends with Oprah, who made an appearance at the infamous 30th birthday party.He appeared on the Oprah Winfrey show in 2009 opening up on the ups and downs of his life to date, from being bullied as a child to the death of his four-year-old daughter Exodus in a household accident.And on the same show, he made up with fierce rival Evander Holyfield.When Oprah saw the film of the interview, she was struck by Tyson’s vulnerability.She said: “I was so impressed with what you were able to reveal about yourself. “It feels like it’s more than about you – it really is a study in humanity.”In 2021, Tyson would appear with Oprah again on Tom Brady’s Let’s Go! podcast.Mike Tyson opened up to Oprah Winfrey in a famous interview that saw him bury the hatchet with Evander HolyfieldCredit: Harpo ProductionsJAKE PAUL VS MIKE TYSON: ALL THE DETAILS YOU NEED AHEAD OF HUGE BOUTEvander HolyfieldPerhaps the most unlikely of Mike Tyson’s celebrity friendships is with his biggest ever boxing rival.For all his triumphs in the ring, Iron Mike is perhaps best known for biting part of Evander Holyfield’s ear off in their second fight in 1997.But the two made up in a joint appearance on Oprah.Tyson said on the show: “This is a beautiful guy, me and this guy both come from basically the sewage, and we watched each other grow to become established and esteemed fighters, you know what I mean?””And I just want you to know it’s been a pleasure passing through life being acquainted with you.”And two years ago they even went into business together, creating an edible cannabis product in the shape of Holyfield’s ear.Arch rival Evander Holyfield became close friends with Mike Tyson and they even launched their own cannabis product togetherCredit: RexBut he didn’t get on with everyone…In his memoir Undisputed Truth, Mike Tyson told an astonishing story about Brad Pitt.The actor is claimed to have made the A-list of stupidity by sleeping with the feared former heavyweight champ’s wife.Tyson claimed that he walked in on Pitt and his ex-wife Robin Givens having sex, with the Hollywood star shouting “dude, don’t hit me, don’t hit me” when he realised he’d been caught.In the memo, the boxer wrote: “You had to see the look on his face. He looked like he was ready to receive his last rites. He also looked stoned out of his gourd.”But Givens denied the claims in an interview with Andy Cohen.READ MORE SUN STORIESShe said: “Pulling up in the driveway? That part’s true. I thought he said he caught us in bed. “I didn’t read the book, but I was told he said he caught us in bed, which never happened. Never, ever, ever happened.”Mike Tyson claims he caught Brad Pitt in bed with his ex-wifeCredit: Getty More
