Frank Sinatra’s ties to the Mafia have long been speculated about, but never confirmed. However, a new book has recently come out that claims to have the inside scoop on the matter. According to the book, Sinatra was not only friends with some of the most notorious mobsters in history, but he also did their bidding on occasion.

Lucky Luciano

While it is not a secret that Sinatra was friends with some of the biggest mobsters in history, including Lucky Luciano and Sam Giancana, the new book claims to have evidence that there was more to their relationship. Apparently, before his rise to fame as a singer, Sinatra worked as a delivery boy for Lucky Luciano, who was at the time, involved with the mafia’s business dealings.

While it has long been rumored that Sinatra made frequent deliveries to Lucky Luciano in New York, the new book claims to have proof of his involvement. The author of the book is claiming that before Sinatra became famous, he worked as a delivery boy for Luciano, and would deliver messages and packages for the mobster.

His Wild Lifestyle

In addition to his ties to the Mafia, Sinatra was also known for his wild lifestyle and womanizing. He had several high-profile affairs, including one with actress Marilyn Monroe. In fact, some have claimed that Sinatra was the one who introduced Monroe to John F Kennedy.

His Temper

In addition to his ties to the Mafia, Sinatra was also known for his volatile temper. He was often involved in fights and brawls with other celebrities. In fact, he once got into a fight with Dean Martin that resulted in both men getting arrested. Some have speculated that this was the reason why Martin refused to play in “The Rat Pack.”

His Friendships

While Sinatra’s relationship with Luciano has long been speculated about, his ties to other mobsters are also coming under scrutiny. The new book claims that not only did Sinatra try to help mobster Sam Giancana out of prison, he also attempted to get Giancana off the FBI’s most wanted list.

The book claims that before his death, Sinatra was trying to secure a Presidential pardon for Giancana. However, the plans were cancelled when it was revealed that Giancana had apparently planned on using his connection with Sinatra in order to win favor with the Kennedy family.

While much of this information is new, it is still just speculation. Sinatra’s ties to the Mafia have never been confirmed, and his friends and colleagues have always denied any involvement. However, the new book does provide some interesting insight into the singer’s mysterious past.


Despite his ties to the Mafia and adulterous behavior, Sinatra has remained one of the most beloved singers of all time. Even today, he is known for his talent and many are still enamored by his charming good looks.

Despite his troubles with the law and his ties to organized crime, Sinatra is remembered as one of the greatest singers in history. He was well known for hits such as “My Way” and “New York, New York”.