Frank Sinatra Offered To Work For The FBI Despite Alleged Mob Affiliations

Frank Sinatra is a singer and actor that got famous while singing big band numbers. He had an impressive array of hit songs and albums in the 1940s and 50s. He also appeared in several movies and won an Oscar as a supporting actor for his performance in “From Here to Eternity.”

Sinatra’s music career was so successful that his signature songs stretched for multiple generations. When he died in 1998, the singer left behind an incredible catalog of work with iconic songs like “Love and Marriage,” “Strangers in the Night,” and many more.

Besides his music, Sinatra’s alleged connections with the mob made him more popular. The association was strong enough for the FBI to watch him closely and keep a 2,000-page file on him. The singer ignored all this and offered his assistance to the agency. Keep reading to find out what he said and the FBI’s response.

During most of his musical career, Sinatra stayed true to his Italian heritage, which led to rumors about the “My Way” singer’s association with the mob. Sinatra was seen warmly greeting Lucky Luciano in 1947 at a hotel in Havana. There was also suspicion that the singer met with some of Al Capone’s gang members.

Tony Oppedisano, his former manager, revealed that those rumors had little truth in them. Via Page Six, he said, “Wiseguys wanted to be in Frank’s inner circle, and he did his best to juggle that and not let it get too heavy, but you know some people would go overboard.

He added, “Some of the guys became friends over the years, and they would try to do things for him that he never asked them to do. He’d say, ‘if these guys really want to do me a favor, I wish they’d stop doing me favors.” Sinatra reportedly became so frustrated with the “favors” and affiliation that he blamed it on his Italian heritage. Oppedisano said, “He said, ‘it’s only because my name ends with a vowel.”

Around the 1940s, Sinatra’s affiliation with the mob made the FBI start compiling a file against him. His mob ties weren’t the only reason. The singer also held a belief system that was anti-racist and had liberal views. This happened to be in the era of the Red Scare in America, so the crime bureau thought the singer was leaning towards communism.

According to the BBC, the FBI’s compiled file on the singer was over 2,000 pages long and lasted from the 1940s to the 80s. They tried to bug the singer’s home to infiltrate his life, but it was mostly unsuccessful.

In the 1950s, the singer decided to offer his services to the FBI. Sinatra asked to be an informant for the agency, and several people suspected that he did so to stop the rumors about his association with the mob.

The FBI unsurprisingly rejected his request. According to History.com, Herbert Hoover’s aide said in a report, “We want nothing to do with him.” The FBI surveillance showed nothing the public didn’t know. Washington Post reported that the file detailed Sinatra as someone with a “lifelong flirtation” with the mob and a quick temper.

Although Sinatra didn’t have the best relationship with the FBI initially, the agency helped him recover his son from kidnappers. In December 1963, Sinatra’s son, Frank Sinatra jr, was kidnapped for ransom. The requested amount was paid to the kidnappers, and not long after, they released him.

The FBI stepped in and arrested all involved shortly after the release and got back most of the ransom money. Sinatra expressed his gratitude in a letter to Hoover. The letter read, “I would like to express my deep appreciation and thanks for the excellent work of the FBI in securing the safe return of my son, in solving the crime, and for the tremendous amount of work I know they did in assisting the Department of Justice in prosecuting the crime.”

Sinatra had an ever-growing fandom till the time he died. In 1987, an American author named Kitty Kelley released an unauthorized biography of the singer. In the biography, she accused Sinatra of using his affiliation with the mob to build his career.

Her claims did nothing to reduce the actor’s popularity, and in 1993, he gained even more fans when he released “Duets.” The album was a huge hit; however, some critics weren’t too sure of the quality of the work because Sinatra recorded his parts well before the artists he featured laid their own tracks.

After performing for the final time in 1995, Sinatra died three years later at 82. A more acceptable biography called “Frank: The Voice” was released about the author in 2010 by Doubleday and written by James Kaplan. Kaplan released a sequel to the work in 2015 titled “Sinatra: The Chairman.”