The Bet – Old Hollywood blind

This mob boss had always wanted to sleep with this alliterate A list actress, but she had always rebuffed his advances.

He was not used to people saying no to him.

So, he reached out to this permanent A list singer  and asked for his help.

The singer said he could get the actress to be anywhere the mafia boss was going to be, but the boss didn’t believe him.

They literally bet $100K on whether or not the actress would show.

The actress, who had recently divorced a husband, was in bad shape and self-medicating a lot.

The actress showed up but still wasn’t interested in the mafia boss.

He wasn’t taking no and the boss and the singer not only sexually assaulted the actress for two straight days themselves, they brought in others too.

She died shortly thereafter.

Mob boss: Carlo Gambino

Actress: Marilyn Monroe (Her ex husband: Arthur Miller)

A list singer: Frank Sinatra

Frank Sinatra’s complex relationship with the mob included activities like serving as a “bag man,” which involved carrying a suitcase filled with $2 million in cash to Cuba in 1947 during a mob celebration for Lucky Luciano’s release from jail. This incident highlighted Sinatra’s close ties with prominent mobsters, reinforcing his reputation for having mafia connections​.

Sinatra’s connections extended into his professional life, reportedly affecting his career trajectory. It is claimed that mobster threats helped Sinatra secure his Oscar-winning role in From Here to Eternity. This supposed intervention involved mob figures pressuring the film’s production to cast Sinatra, although he always denied such claims​.

Further intertwining with the mafia’s influence, Sinatra reportedly played a role in arranging meetings between Judith Exner, a woman he dated, and President John F. Kennedy. Exner, who later claimed to have been involved with both Sinatra and Kennedy, also had connections to the mob through Chicago mob boss Sam Giancana, a figure she was introduced to by Sinatra​.

Sinatra’s connections weren’t limited to Giancana. Throughout his life, he was seen with various other mob figures, impacting his personal and professional life. For example, he was forced out of casino operations at the Cal-Neva Lodge due to pressures from gaming commissions aware of his mob associations​.

While Sinatra’s ties to the mob are well-documented, his relationship with Marilyn Monroe appears more speculative and less substantiated by concrete evidence. Monroe’s own storied life intersected with many high-profile figures, and while she and Sinatra were part of the same social circles and Hollywood scene.

Marilyn Monroe ‘spent her last night with mafia boss Sam Giancana at Frank Sinatra’s lodge’

Sinatra’s interactions with the mob provide a fascinating glimpse into the overlapping worlds of entertainment, politics, and organized crime during his era. His legacy, as a result, is not just as a musical icon but also as a figure with complex, and sometimes controversial, affiliations that stirred public and media interest throughout his life.

Who is Carlo Gambino:

• Carlo Gambino was born on August 24, 1902, in Palermo, Sicily, Italy. He later immigrated to the United States with his family in 1921, settling in Brooklyn, New York.
• Gambino rose through the ranks of organized crime in New York City during the early 20th century, becoming associated with the Mafia, specifically the Cosa Nostra.
• He served as an underboss to Albert Anastasia, a prominent mobster and one-time head of the Gambino crime family.
• Gambino allegedly orchestrated the assassination of Anastasia in 1957, which allowed him to take control of the crime family.
• Following Anastasia’s death, Gambino assumed leadership of what became known as the Gambino crime family, one of the “Five Families” that dominated organized crime in New York City.
• Under Gambino’s leadership, the Gambino crime family expanded its operations into various illegal activities, including extortion, loan sharking, gambling, and narcotics trafficking.
• Unlike some other mob bosses who sought public attention, Gambino preferred to keep a low profile and operate discreetly, earning him the nickname “The Quiet Don.”
• Gambino was known for his ability to forge alliances with other criminal organizations and maintain control over his family’s operations, making him one of the most powerful mob bosses in American history.
• Despite his efforts to avoid public scrutiny, Gambino was not immune to law enforcement. He was indicted several times during his criminal career but managed to avoid significant jail time.
• Carlo Gambino died of a heart attack on October 15, 1976, at the age of 74. He left behind a lasting legacy as one of the most influential and successful Mafia bosses in American history, with his crime family continuing to wield power in New York City for decades after his death.