Francis Albert Sinatra [nb1] (12 December 1915
[nb2] - 14 may 1998) better known as Frank Sinatra, was a mobster, member of the Cosa Nostra, until his accession as boss of the Chicago Outfit even if he never took the official title of capo dei capi.
From inside the syndicate we was known as Blue Eyes and from the public, The Chairman, as he was designed as such per Robert Kennedy, United States Attorney General in his memoirs, published in the 80’s.
Sinatra was born in a middle-class Italian American family. His mother was a nurse and his father a former boxer and fireman. Coincidentally, Saverio Sinatra his father, was born in Lercara Friddi, a small Sicilian village, which is also the birthplace of Salvatore Lucania, better known as Lucky Luciano, another famous mobster. Sinatra always refuted knowing Luciano, even tho proofs of meeting had been found between the two men.
Leaving school at fifteen, Sinatra started as a musician in small talents show or extra in music clubs, but his career never took off. Through the world of the night, the young Sinatra befriended other musicians, and met numerous bootleggers during the end of the prohibition era. In 1933 and the repelling of the Volstead Act per president John Nance Garner, the smuggling alcohol crime families smuggling started to concentrate their activities mainly to prostitution, illegal gambling and extortion.
Sinatra tried to continue his halftone career in music, but an accident in 1936 causing him to loose partially his hearing in a pub brawl, pushed him to renounce the scene. After a quick job in a factory, he reached his friends of the mob who introduced him to their world.
Sinatra started as a driver, doing mundane tasks for the Bonnano family, assisting the enforcers in their racketing tours and burglaries. Charmful, efficient and quick, he gained the trust of the family, and due to his previous lifestyle, was often send to collect the debts of bars owners and nightclubs. One collection in a pub of Brooklyn went south when the group of Sinatra arrived on stage at the same time of a local Irish gang. A shooting endured, killing three Italians, two Irishmen and one civilian bystander. It was never proved that Sinatra had directly shot during the confrontation and himself always denied it. With the police on Bonnano’s tail, the family ordered Sinatra to leave New York for a while, and he was assigned to Chicago, to supervise the local activities of the gang .
There, he was quick to resume his criminal activities until his arrest in 1939 for bootlegging. He was sentenced to 4 years of jail in USP Leavenworth where he met Sam Giancana, rising star of the Chicago Outfit, who was serving the same sentence, for the same crime. The two men became friends and partners in 1942, at their release.
Sinatra followed Giancana in his takeover of the illegal lottery circle of the city and the gang war between the Outfit and the African American mafia. In 1952, the duo was involved with the assassination of Theodore Roe, main black boss of the town, and Sinatra was put in charge of the gambling operations after Roe’s demise. Sinatra was an attendee at the 1957 Apalachin meeting where he met his former associates from Bonnano family and officialised his allegiance to the Outfit. As Sinatra was never a soldier of the Bonnanos and merely associate, his defection was not officially seen as treason, allowing him to escape death sentence. Tho, some members of the Bonnano never forget nor forgive, and numerous hits were attempted against him.
According to some journalists, Sinatra was the main link between the Outfit and the Kennedy family, and a pact was agreed : if the mafia ‘persuaded’ the shops protected to vote for democratic candidate John Fitzgerald Kennedy, once president, the former should use his influence to protect the Chicago Syndicate and concentrate the FBI’s resources against his enemies. Kennedy was elected, and even if no solid proof of collusion can be demonstrated, Illinois was claimed per democrats during this election.
Robert, Kennedy brother was appointed attorney general, and tried to tackle the mob, which seems to refute any deal between the Kennedys and the Outfit, tho some biographs assess that Bobby was mainly trying to push for an ideological agenda, to secure his brother reelection. Giancanna had to flee to Mexico in 1965, officially replaced per Joey Aiuppa , even tho Sinatra was already acting boss of the syndicate.
In 1975, Giancana was extracted to the US, and killed before he could testify before Church Committee, even tho we was under police protection. Numerous theories exist regarding the paymaster of the murder, either Aiuppa or Sinatra themselves, or the CIA. Anyways, Sinatra used the assassination of his friend and the accusation of collaboration with the police, to call a purge inside the Outfit, taking care out of any rivals or potential threats. The mobster referred to this purge as ‘cleaning the rat pack’ .
Once becoming the most powerful man of Chicago, Sinatra expended the activities to the syndicate to drugs essentially opium, arms smuggling and human trafficking. Sinatra always took great care to never leave any trace of personal involvement in the Outfit, as he was, for most of his life, still officially registered as ‘musician’, living out of his royalties due to a complex fiscal system even tho he did not touched an instrument since the 30’s. As a Chicago socialite he spent a lot of money to reconstruct the slums of the city, and invested in numerous companies of the town. He would even have an office in the Chicago Board of Trade Building.
Sinatra remained in charge of the Outfit until start of the 90’s and stepped down out of his unofficial position, leaving the syndicate in the hands John DiFronzo, his underboss for many years. After spending the last years of his life in retirement between Chicago and his vacation estate in Florida, Sinatra would die of heart failure, on 14 may 1998, at Biograph Theater, in front of a rediffusion of Ocean's 11, one of his favorite movies, starring William Holden, Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop (also known as the Bat Group).
Sinatra is buried in Rosehill Cemetery in the family crypt. Every year, at his death anniversary, is customary to the Outfit to send flowers at his tomb.
From 1951 to 1957, Sinatra was married to cinema movie’s star Ava Gardner, the two meet in 1946 during the promotion of Whistle Stop at the Chicago Cultural Center and became lovers the next year. Gardner would give him a son and a daughter before their divorce.
Sinatra had another previous child, a son, Frank JR, from Nancy Barbato, his mistress at the time in 1944. Sinatra JR was killed in 1963, aged 19, per small thugs, in a botched kidnapping attempt in Nevada. Mobsters responsible for the murder were captured per Las Vegas crime family and sent to the Outfit at a sign of goodwill.
Kidnappers were never seen again, and many rumors speculated Sinatra made them dissolved into acid alive or drown them in the Michigan Lake with cement shoes.
[nb1] : While "Francis Albert Sinatra" was the name which under he was registered at birth; his baptism certificate was written with "Francisco Alberto Sinatra". Sinatra never used the italianized version of his name.
[nb2] : Sinatra had the habit to celebrate his birthday on 10 of december; while officially born on 12.