Infamous New York

Reformed gangster and member of Johnny Torrio’s first gang, Roxie Vanella opened this funeral parlor at 29 Madison Street.

Location: 29 Madison Street: Vanella’s Funeral Chapel

Status: Standing

He was the King of the Ragpickers and the Mayor of James Street. He knew judges and congressmen, and was a personal friend of Johnny Torrio, Al Capone, and Presidential Candidate Alfred E. Smith. His name was Robert “Roxie” Vanella, an ex-gangster turned prohibition-era undertaker who was the namesake of Vanella’s Funeral Chapel located at 29 Madison Street in one of the last-vestiges of the old Corlears Hook neighborhood.

A Young Man, Willing to Do Anything:

Born and raised in a district ruled by river pirates and street walkers, Vanella was born in a bleak tenement at 68 James Street, giving him virtually no other options but a life of crime.  In 1899, the sixteen year old Vanella proved his desperation by posting a classified ad in the New York Herald, which stated:

The ad was a surprisingly accurate resume, and Vanella went on to prove that he was in fact, “Willing to do anything.”

Johnny Torrio and The James Street Gang

He became best friends with Johnny Torrio, whose stepfather ran an illegal moonshine still across the street from Vanella’s home, and together they founded The James Street Gang, an East River auxiliary for Paul Kelly’s Five Pointers.

By 1907, the duo had parted company. Torrio relocated to Brooklyn, while Vanella moved to Montana, a strange place for an Italian from New York to say the least. While he was in the Big Sky State, Vanella’s traveling companion suddenly died of an acute gunshot wound to the head. Vanella claimed it was suicide and the cops claimed it was murder. The jury believed the cops, and they slapped Vanella with life in prison.

Ethel Eppstein would help Vanella win his freedom from a Montana Prison

After serving seven years in the Deer Lodge Penitentiary, Ethel Eppstein, a socialite prison reformer investigated Vanella’s case and found that he had been convicted on circumstantial evidence. In 1914, the state granted a re-trial and the New York gangster walked out a free man.

Johnny Torrio and Roxie Vanella: Together Again

After beating a life sentence, Roxie headed straight for Chicago where his old pal, Johnny Torrio, had become a big thing, managing Big Jim Colosimo’s brothel empire in the Levee District.It didn’t take long for the slugs to start flying.

Roxie and Torrio kicked off a shootout that left a policeman dead and Vannella wounded, but once again, Roxy beat the charges. However, after dodging two life sentences in a seven year period, the gangster smartened up and went straight. Click to read the newspaper story on Vanella.

Once again proving that he was willing to do anything, he returned to James Street where he joined the staff of Tammany Hall’s Big Tom Foley, was elected President of the Ragpickers Union, and opened Vanella’s funeral chapel where he made it big burying the casualties of the roaring twenties.

Vanella’s Funeral Chapel located at 29 Madison Street.

Torrio never forgot Roxie. When the Mayor of James Street wed in 1921, the New York Tribune reported:

John Torrio, the best man, well known in Chicago politics, came in a special [train] car, bringing a party of fifty with him.

One can only imagine the identities of Torrio’s fifty associates. Click to read the full story of Vanella’s wedding.

If anyone else has any info on Vanella, I’d love to hear it.