Antonio Vanella: A Deadly Serious Hoodlum and Prolific Gangster!


Antonio (Tony) Vanella – aka “Anthony Santini”, “Anthony Vanilla”, “Anthony Milo”, “Big Tony”, “The Chief” – was born in Godrano, Palermo province in Sicily on September 16, 1894. He immigrated to this country at the age of five with his father and mother on May, 18, 1899.

Vanella first settled into the Lower East Side living on Catherine Street. He later moved up to the Bronx for a time where he resided at 2027 Webster Avenue.

Years later, after being paroled from prison, he moved back to Lower Manhattan, living at 45 East End Avenue with his wife Gilda (Gloria). He and his wife never had any children.

By the mid-1960’s he had moved out to the Astoria section of Queens County where he would live for the remainder of his life.

Side Note: In 1956, Vanella voluntarily left the United States for Italy in lieu of deportation, with permission and the stipulation that he could re-enter as a permanent resident. He re-entered in June of 1956 and was a registered alien.


#A2834314.-FBI # 769770


His activities included organized armed-heists, stock thefts and frauds, strong-arm tactics, extortion, and gambling.

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Between the years of 1914 and 1940, Vanella was mostly in jail on various armed robbery convictions.

In 1920, he’d first been convicted on a first-degree robbery charge and jailed for an indefinite term.

Then in Brooklyn, early in 1924, he was again indicted on robbery, grand larceny, and assault for the well-publicized major armed-theft committed back in 1920 of two bank messengers who were accosted on a midtown street and robbed of a package containing $466,000 in highly sought after negotiable securities.

With previous second-offender status, he was subsequently tried, convicted, and sentenced in April of 1924 to serve 40-years of “hard labor” up at Sing Sing Prison.

While Vanella was serving his term at Sing Sing, he was one of 16 prisoners hauled out of their cells and shipped out further Upstate NY to Clinton Penitentiary – known as “Siberia” because it was only several miles proximity to the Canadian border and feared for its extremely harsh living conditions.

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He was charged with a possible escape attempt after a close inmate associate was found with a “dummy” propped up in the bed of his jail cell, setting the stage for the planned escape.

Authorities shipped each suspected conspirator to a different prison so as to disrupt any plans they had.

After finally being paroled from a long prison stretch in August of 1940 (Tony had served 16 years straight), he was said to have become a partner of Gambino consigliere Joseph Riccobono aka “Staten Island Joe”, in a Manhattan garment manufacturing firm.

He was also alleged to be active in garment center extortion and shakedown rackets in accord with Riccobono.


Side note: Vanella tried several times in vain to have his parole restrictions rescinded by the courts but was always denied. He’d had his original sentence shortened by the governor of the state allowing him to make parole the first time, but that’s all the “courtesy” he was gonna get!


And although little-known to the general public, Tony Vanella was indeed identified and widely-known on the streets as a formally inducted respected “soldier” in the Anastasia/Gambino Family and had the reputation as a “tough guy”.

Big Tony Vanella was indeed listed as a “button man” by both federal (FBI) and local (NYPD) law enforcement that had repeatedly declined to prosecute him on several “anti-racketeering” (AR) investigations in 1956 and 1957.

During Vanella’s arrest in 1957, the arresting agents seized his address book on a nightstand in his apartment. In it were among the following names of various criminal associates. He admitted to knowing and being friendly with all those named in the address book:

• Joseph (Joe Socks) Lanza – FBI #795896 – the czar of the Fulton Fish Market.

• John (Johnny Dio) Dioguardi – NYPD #B-114267 – well-known industrial racketeer and labor union corrupter.

• Thomas (Tommy Dio) Dioguardi – NYPD #B-88595 – John’s brother and himself a prolific garment racketeer.

• Michael (Mickey) Bowers -NYPD #B-52094 – notorious Westside waterfront racketeer, president of a ILA Longshoreman’s Union – the so-called “pistol local”, and a boss of the “Arsenal Mob”.

• Anthony (Tough Tony) Anastasia – FBI #4743827 – brother of Albert, boss of ILA -Local #1814, and czar of the Brooklyn waterfront.

• Joseph (Gus) Colozzo – NYPD #B-189380 – another union official and Brooklyn waterfront racketeer.

• Joseph Keefe – NYPD #B-62567 – well-known westside Irish hoodlum and Dock racketeer.

• Julius Friedman – NYPD #B-67820.

• Paul Silagi – prison #E-33987 – a former Sing Sing prison buddy.

• Morris (Judge) Trackiner – a well-known Albany based hoodlum and former prison buddy.

• James (Jimmy Doyle) Plumeri – top Lucchese capo and garment rackets figure for decades

…and additional assorted criminals and hoodlums such as:

• Abraham Wolf – NYPD #B-64556.

• Roderick Lucci NYPD #B-236156

• Harmon Rich

• Solomon (Solly) Fingar

• Nathan Brodsky

…. many of his closer above named associates were active in waterfront racket operations on the piers, or the garment district.

It makes sense that Vanella was also actively engaged in such activities himself. He admitted a partnership with Abe Wolf in a “zipper” association based in the garment district.

Tony Vanella was also the registered owner of the Highway Salvage Co., in NYC.

By the late 1960s, he was no longer in the streets and was slowing down.

He died in 1971 at the age of 77 years old.


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Back to The Gambino Family

The Genovese Family

The Bonanno Family

The Colombo Family

The Lucchese Family

The DeCavalcante Family


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