Frank Sinatra, the legendary crooner known as “The Chairman of the Board,” had a deep disdain for the media linking him to the Mafia, according to his former road manager Tony Oppedisano.

In a new book about his time with Sinatra called “Sinatra and Me, In the Wee Small Hours,” Oppedisano explains that Sinatra believed the only reason he was portrayed as being connected to the mob was because of anti-Italian sentiment.

Oppedisano quotes Sinatra as saying, “It’s only because my name ends in a vowel.”

The road manager went on to explain that Sinatra only came into contact with wiseguys because they owned the nightclubs where he performed.

He would tell Oppedisano, “Tony, I don’t get it. If the nightclubs were all owned by cardinals and monsignors, I guess I would have been spending time with cardinals and monsignors, but that doesn’t make me a cardinal or a monsignor, nor does working in a club that was owned by wiseguys make me a wiseguy.”

Oppedisano also revealed that Sinatra had a simple explanation for the photos of him posing with mobsters.

He would tell his friend, “I was raised that when a man offers his hand to shake my hand, I never asked him how he came about the money in his pocket before I shook his hand. Polite is polite.”

However, Oppedisano stated that mobsters were eager to be associated with Sinatra and would compete for his attention and friendship, including notorious mobster John Gotti.

The road manager remembered, “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. 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!'”

Despite Sinatra’s insistence that he had no mob ties, the FBI had evidence to the contrary. Files released after the singer’s death showed that he had a close friendship with Chicago mob boss Sam Giancana.

Sinatra even reportedly introduced Giancana to John F. Kennedy’s campaign team in 1960 in an effort to secure votes for the Democratic candidate.

Additionally, there were files on gifts received from mob brothers Joseph and Charles Fischetti, a performance at the wedding of Philly mob boss Angel Bruno’s daughter, and documentation that revealed the mob exerted pressure to help Sinatra wiggle out of a 1951 contract.

The situation over that contract with band leader Tommy Dorsey is similar to a subplot in the movie “The Godfather” involving the mob-linked crooner character Jonny Fontaine, which Sinatra believed was based on him.

Sinatra was so sensitive to being connected to the Mafia in the film that he reportedly once berated “Godfather” author Mario Puzo in a Beverly Hills nightclub.

Oppedisano’s book also includes lighter moments from his time with Sinatra, such as his encounter with the singer’s second wife, Ava Gardner.

He recounts chatting with Gardner and Sinatra crony Jilly Rizzo about male pals and the conversation somehow turned to Sinatra’s third wife, Mia Farrow.

Gardner allegedly said, “He finally found something that he’s been looking for his whole life. A boy with a c–t,” shocking Oppedisano and Rizzo.

Despite Sinatra’s denials of having any connections to the Mafia, it is clear that he had relationships with known mobsters and that the FBI had evidence of these connections.

However, according to Oppedisano, Sinatra believed that these connections were solely due to the fact that many nightclubs were owned by mobsters and that he had no choice but to interact with them.

He also believed that the media’s portrayal of him as having connections to the mob was due to anti-Italian sentiment.

Sinatra’s sensitivity to the subject is evident in his reported confrontation with “The Godfather” author Mario Puzo and the similarities between the character of Jonny Fontaine and his own life.

However, it is important to note that the FBI’s files and Oppedisano’s account both show that Sinatra did indeed have connections to known mobsters, regardless of his personal feelings on the matter.