In the mostly unreachable world of celebrity lifestyle, it seems like having connections in all the right places helps keep Hollywood stars, athletes, and even politicians on the road to success and media attention. Sometimes these connections can be to well-known actors, producers, directors, or other people in places of power. However, there are times when even celebrities connections aren’t so well regarded and operate on the other side of the law. It’s no secret that rappers often proudly throw up signs representing street gangs like the Bloods or the Crips, such as Snoop Dogg and B-Real from Cyprus Hill.
However, there are some less obvious and even surprising celebrities that have connections to the criminal underworld. Some have seemingly flawless reputations that are an inspiration to others the world over, and others are in the public eye or are in positions of power and high status. We will take a look at 15 surprising celebrities that either have or have had connections to the criminal underworld, from street gangs to the Italian mafia, as they made their way to the top.
15 Usain Bolt - Publicly Supports The Gaza Crew
Eight-time Olympic gold medallist sprinter Usain Bolt is without a doubt one the best and most popular athletes of all time. He holds world records in the 100 meters, 200 meters, and the 4 x 100 meters relay race. In addition, Bolt is an eleven-time world champion, the face of Virgin Media, and a talented reggae DJ. Bolt is one of the most inspirational sports stars in the world.
However, even his squeaky clean has been known to get a little dirty with his public support for Vybz Kartel, a Jamaican reggae star and the imprisoned leader of one of the most notorious street gangs in Jamaica known as The Gaza. Bolt has openly supported Kartel’s early release through a social media campaign called the “Free the Gaza Boss" in 2015 and is pictured throwing up several gang signs in photographs.
14 Son's Of Anarchy's Happy Is A Real-Life Hell's Angel
David Labrava is best known for playing one of the main characters in the biker-themed crime drama the Sons of Anarchy directed by Kurt Sutter and starring Charlie Hunnam and Ron Perlman. David played the loyal SAMCRO member, enforcer, and Sergeant-At-Arms Happy Lowman, and was part of the show from season one.
David Labrava was originally hired to be a technical adviser before he was cast as Happy. The reason for this was because of his invaluable first-hand knowledge as a real-life member of the Hell’s Angels Motorcycle Club.
Although David refuses to acknowledge that the Hell’s Angels are involved in any kind of criminal activity, the club’s history and notoriety are very well-documented. In addition, he was hired for his expertise on the matter of biker gangs in a show that focuses heavily on crime and violence, so it’s more likely that he’s keeping a code of silence.
13 Dana White - Dealings With The Winter Hill Gang
Dana White is the president of the UFC (Ultimate Fighting Championships), which is the biggest and most mainstream mixed martial art organization in the world. White became the president after finding out the company was for sale during his time managing former UFC fighter Tito Ortiz. He contacted childhood friends Lorenzo and Frank Fertitta who subsequently purchased the company and installed White as the president.
However, before Dana White became involved with the UFC he ran a boxing gym in Boston which attracted the attention of the Winter Hill Gang run by Irish mobster Whitey Bulger. White tried to work out a deal with Bulger, but it didn’t go his way and the gang wanted $2,500 “protection money.”
White received some serious threats from the gang to pay up within 24 hours. So he packed his bags and left for Las Vegas the same day. Obviously Dana White has never looked back as under his leadership the UFC has become a multi-billion dollar industry. Bulger, however, is serving two life terms in prison.
12 Tamer Hassan - His Uncles Were Ex-Bank Robbers
British actor Tamer Hassan has starred in several well-known films and television shows, such as Layer Cake with Daniel Craig, Batman Begins, Clash of the Titans, Game of Thrones, 24: Live Another Day, and Snatch.
Tamer is often playing tough gangsters from London’s criminal underworld, but in real life he grew up around true life villains because his uncles were bank robbers from the 1970s and the 1980s.
Tamer has used his real experiences to help bring a sense of authenticity to his roles and the new television adaption of Guy Ritchie’s Snatch. He apparently took his cast mate and friend Dougray Scott to see his uncles so Scott could portray the mannerisms and qualities needed to portray the role without acting like a pantomime villain.
11 Conor McGregor - Kinahan Irish Mob
For anyone that’s followed the even a part of Conor McGregor’s career, it’s fairly obvious that the two-division UFC champion has a fascination and to some degree an obsession with the gangster lifestyle. He wore a blue patterned shirt that was a reference to the Mexican drug lord Joaquin “El Chapo” Guzman. In addition, he even posed in images with guns referencing the Al Pacino film Scarface.
However, McGregor’s “wannabe” gangster-style antics have crossed the line into reality on several notable occasions in his pursuit to appear “connected.” He's been seen on many occasions in the same social circles as the late David Byrne, who fell prey to notorious Dublin gang war in 2015 and was a member of Kinahan gang, which is involved with drugs and weapons smuggling.
10 Joe Namath - Associated With Two Crime Families
Joe “Broadway Joe” Namath is a Hall of Fame former professional American football quarterback that played for the New York Jets and the Los Angeles Rams NFL and the AFL during the 1960s and the 1970s.
Joe’s connection to the mob came as a result of owning shares in a Manhattan-based bar called Bachelors III which attracted celebrities, politicians, but most notably members of the Gambino and the Lucchese crime families.
The NFL commission forced Joe cut all ties with the bar, but there were allegations of him fixing games and even though they were never proven, his social circles certainly added to the controversy and raised a few eyebrows.
9 Liz Hurley - Romantically Involved With A Capo Of The Colombo Family
Liz Hurley is a model and actress that first gained media attention as Hugh Grant’s girlfriend and attending Los Angeles premiere of Four Weddings and a Funeral in a now-famous Versace dress held together by gold safety pins.
Her best-known film roles include the Bedazzled when she played the Devil with Brendan Fraser, and as Miss Kensington in Austin Powers: International Man of Mystery with Mike Myers.
In 2001, another Liz Hurley relationship gained some more media attention when she got involved with a captain of the Colombo crime family Dominic “Donnie Shacks” Montemarano after they were spotted together holding hands, although it's unknown how long they were involved.
8 Marilyn Monroe - Spent Her Last Night With A Mobster
Marilyn Monroe was one the most popular and well-known, and iconic female actresses and performers of the 1950s and is the considered one of the most recognizable pop culture icons of all time.
Sadly, despite appearances, Monroe had a complicated battle with anxiety, depression and substance abuse. As a result, her private life gained a huge amount of unwanted media attention, all of which likely paid a part in her untimely passing at the age of 36 in 1962.
According to Marilyn Monroe’s personal hair stylist and friend George Masters, she spent her final night with Sam Giancana, the head of the Chicago Outfit – a man she was in love with – at Frank Sinatra’s lodge. There he apparently tried to convince her not to go public about her affair with President John F. Kennedy.
7 Dino Bravo - Former WWE Wrestler Upset The Wrong People
Fans who grew up in what many consider to the golden age of WWE wrestling will remember the Italian-born Canadian powerhouse who was regularly matched up against the likes of Hulk Hogan, and the Ultimate Warrior and was a member of the Dream Team with Greg “The Hammer” Valentine.
However, Dino Bravo’s career with the WWE came to an end in 1992, and without any other work experience beyond wrestling, he was lured into a crime to pay off his debts and expensive mortgage and keep a roof over his wife and daughter’s heads by his mafia boss uncle.
Dino got into the lucrative cigarette smuggling business and started making a lot of money. Other mobsters started taking notice and wanted in, offering Dino a cut of their drug smuggling operations. Unfortunately for the former wrestler, the police intercepted $400,000 worth of cigarettes and Dino was blamed for the botched pick-up. According to Bret Hart, Dino apparently confided to his friends that his days were probably numbered, and unfortunately at the age of 44 that prediction came true.
6 Jerry Orbach - Close Friends With Crazy Joey Gallo
Jerry Orbach was an actor from the Bronx, New York that found worldwide fame for his supporting role in Dirty Dancing with Patrick Swayze and as the NYPD Detective Lennie Briscoe in NBC’s crime series Law & Order.
During the 1970s Jerry was a very big name in Broadway and film and was a close personal friend of Joseph “Crazy Joey” Gallo of the Profaci crime family. The pair became friends after Gallo objected to the way Orbach portrayed a mobster in the film The Gang That Couldn’t Shoot Straight, which they discussed over drinks. After this, they operated in the same social circles and even Orbach’s wife described him as charming and funny.
Unfortunately, during an evening out in 1972 with Jerry Orbach and his wife, Gallo’s mob life caught up with him. Orbach was a witness to the crime but never revealed any information about the incident to the police.
5 Billy Murray - The Krays Paid For His Acting Lessons
Essex-born Billy Murray is often cast as London gangster in films like Rise of the Footsoldier, and The Rise and Fall of a White Collar Hooligan. Video game fans will know him as the voice of Captain John Price in the Call of Duty: Modern Warfare series.
After Murray left school, he boxed for the West Ham Boxing Club, which was owned by Reggie and Ronnie Kray, two of London’s most notorious and infamous gangsters – both played by Tom Hardy in the 2015 film Legend.
However, in an act of kindness because they “liked his attitude,” they paid for Murray to attend acting school and never asked for the money back. Murray also acted as a character witness for their brother Charlie Kray in court after he was arrested for drug smuggling.
4 James Caan - Friends With The Colombo Crime Boss
James Caan is one of the biggest names in Hollywood and has starred in films like The Godfather and the Godfather Part II alongside Al Pacino, Robert DeNiro, and Marlon Brando.
James however, doesn’t just include Hollywood’s rich and famous as his friends but he isn’t ashamed of counting members of the Colombo crime family as his friends. Caan even publicly supported Colombo boss Andrew “Andy Mush” Russo, by offering to pay his bail when Russo was arrested by the FBI.
Caan and Russo are so close that Russo was revealed to be the godfather to his Scott Caan the star of the US TV crime series Hawaii Five-0. Caan was so connected that he even asked members of the mob to have a “talk” with Joe Pesci after a disagreement of an unpaid hotel bill.
3 Tony Sirico - Former Associate Of The Colombo Crime Family
Tony Sirico is an actor that has starred in films The Godfather Part II, Goodfellas, Cop Land, but he gained worldwide fame as Paul “Paulie Walnuts” Gualtieri in television series The Sopranos.
As Paulie, Tony brilliantly played a character that was both funny and terrifying in a convincing way. The reason for this was because he was able to draw from his past as an associate of the Colombo crime family in New York City.
Sirico was arrested 28 times, convicted twice, and deemed a danger to society before deciding to pursue acting. He developed the passion for acting after watching an acting troupe of ex-convicts performing at the prison where he was serving his sentence.
2 Frank Sinatra
The Academy Award-winning Frank Sinatra is considered to be one of greatest singers and entertainers of all time. He was also associated with the Italian Mafia. Although it’s no secret that many of Hollywood's elite were seen in the same circles as members of the mafia, Sinatra’s connections, however, go much deeper than a few friendly drinks on the nightclub scene.
Sinatra’s first connection to the mob is from family, as his uncle Babe Gavarante was a member of the Bergen County armed robbers who, in turn, were linked to the Moretti organization. His first wife was the cousin of one of Willie Moretti’s senior henchmen, and he even sang at their daughter’s wedding.
Sinatra was close friends and associated with notorious Chicago mobster Charles Fischetti and Atlantic City gambling boss Paul D’Amato. In addition, Frank also paid Lucky Luciano $2 million pay allegiance at the infamous Havana meeting for helping further his career.
1 Louis Antonio Ramos - Former Member Of A Street Gang
Luis Antonio Ramos is a Puerto Rican-born actor that was raised in the Bronx, New York. He has had starring roles in Friends, The Shield, The Unit, and most recently, Power with 50 Cent.
Before being given an opportunity to study acting at the New York Performing Arts High School famous for training actors like Liza Minnelli and Al Pacino, Ramos was by his own admission a gangster that grew up on the rough streets of the Bronx.
Ramos dealt drugs on street corners, and in his own words, was a street rat from the projects. Now he’s considered a fantastic character actor that is able to draw from his real-life experiences and can apply them to his gritty portrayals.
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