Photo Essay: An Inside Look at Westchester’s Criminal Past

Read up on these criminal accounts in Westchester. Photo courtesy of the Westchester County Archives

An exploration of the Westchester County archives in Elmsford unearthed old photos that tell of criminal happenings in the region.

Edited by John Bruno Turiano, with research by Lindsey Smith & Gabrielle Beechert

The Westchester County archives, in Elmsford, are a treasure trove of the county’s rich and storied past. While perusing some old photographs there not long ago, we unearthed stories that reveal Westchester’s sometimes-sordid history, ones that involve a rough-and-tumble lot who dwelled in the gloom of dive bars, darkened streets, and back alleys rife with illicit activity and short tempers, as you will see.

O’Reilly/ Barry Robbery & Assault Case, 1929

Bad Deeds Across Three Towns

Crime: Robbery, Assault
Perpetrators: Thomas Barry, aka Thomas O’Reilly, and John Kelly, plus Joseph Heal and Dominick Graziano
Victims: Frank De Ruggiero, the McGennis family, the Lee family, and Officer Robert Philip of Yonkers

Crime of robbery
Photo courtesy of the Westchester County Archives

In the early morning of August 18, 1929, Thomas O’Reilly, John Kelly, Joseph Heal, Dominick Graziano, and a fifth man who was never apprehended arrived at the Roma Gardens, a low-rent cabaret on Taxter Road in East Irvington, in the town of Greenburgh. All were under the influence of alcohol. Their purpose was to see one of the hostesses, an alleged friend of Heal’s. After about two hours of drinking, the defendants started to quarrel among themselves, and four gunshots were fired, one of which struck the proprietor, Frank De Ruggiero. After the shooting, the men fled from the Roma Gardens in a Buick sedan (that had been stolen in New York City earlier), which they wrecked about a mile down the road. The McGennis family were on their way to early church services when they were held up at gunpoint by the men, who took their car and drove toward Yonkers. They then wrecked the McGennises’ car in front of the Lee home, in the village of Hastings, held up the Lees, took their car and again proceeded toward Yonkers. Once in Yonkers, they were stopped by Officer Robert Philip following a running gunfight, exchanging fire as they were chased. Several shots were fired at the officer, one of which struck Philip in the abdomen but inflicted only a shallow wound. O’Reilly was the driver and Heal was the gunman who shot the officer. All four men were convicted; O’Reilly and Kelly, however, who had previous records, received harsher sentences.

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Mugshot, 1917

Career Criminal

Crimes: Assault in the 1st Degree, Carrying a Concealed Weapon (revolver)
Perpetrator: Frank Buonofiglio, alias “Buck O’Neill”

crime of assault
Photos courtesy of the Westchester County Archives

This Mount Vernon resident had a litany of offenses, prior arrests, and sentences beyond the two associated with this mugshot. His listed profession was bartender, though it seems he spent more time stirring up trouble than drinks. Perhaps a more convincing alias would have done the trick.

Sloans Murder Case, 1929

The Missing Cook

Crime: Murder/Sexual Assault
Perpetrator: William “Willie” Sloans, aka Joseph Madison
Victim: Elsa Marshall

Photo courtesy of the Westchester County Archives

Twenty-four-year-old Elsa Marshall was a cook at the Kelly residence in the Knollwood section of Greenburgh and wife of the Kellys’ butler, William Marshall. She went missing on the evening of September 26, her birthday. Marshall alerted police and an all-night search began. Her body was found the next day, in the bushes alongside the road adjacent to Knollwood Country Club, with a shotgun wound to the left side of her body, under the arm. She apparently had been sexually assaulted (her clothing was ripped, and the body lay in a compromised position). Sheriff Thomas V. Underhill initially thought the assault may have been staged to throw off the investigation, implying the shooting may have occurred accidentally, as men often hunted with shotguns in the area.

William “Willie” Sloans, aka Joseph Madison, wasn’t even a suspect until his sister came forward, saying her brother had confessed to accidentally killing Marshall. However, Sloans was also wanted for murder in North Carolina and was sent there to be executed by the state in 1931. Even up to his execution, Sloans maintained that he accidentally killed her but never explained the state in which her body was found.

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Sing Sing Prison Escapee, 1919

$50 Reward For the Man With the Faded Tattoos

Crime: Felonious Escape
Perpetrator: Charles Marchall

crime of prison escape
Photo courtesy of the Westchester County Archives

Charles Marchall, who was incarcerated and serving a sentence for second degree assault, escaped from Sing Sing Prison in October of 1919 after having served not quite a year of his maximum four-year, 10-month sentence. Notable features include a faded tattoo on both back and front of his left forearm, plus a small horizonal scar at lower breast. No record shows he was captured.

Castaldo Homicide Case, 1923

Ace in the Hole or Up a Sleeve?

Crime: Homicide
Perpetrator: Raffaello Castaldo
Victim: Vincenzo Castillo

Crime of homicide
Photo courtesy of the Westchester County Archives

On the evening of August 25, 1923, Raffaello Castaldo, Vincenzo Castillo, and other neighborhood men were playing cards outside of Castaldo’s grocery store at 224 South 7th Avenue in Mount Vernon. An argument broke out concerning alleged cheating on Castaldo’s part. The neighbors broke up the argument between Castaldo and Castillo; later that evening, however, Castaldo retrieved a pistol and murdered Castillo outside of his tenement residence at 229 South 7th Avenue.

Sloane Robbery Case, 1929

Jewel Heist

Crime: Grand Larceny, Robbery
Perpetrator: Roy H. Sloane
Victims: Three office workers at Karos & Stein

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Grand Larceny
Photo courtesy of the Westchester County Archives

Just a few months after he was released from Ossining’s Sing Sing prison, Roy H. Sloane, who was dubbed the “Boy Lawyer” because he studied law while incarcerated, and two other men held up the office of jeweler Karos & Stein in the Miller Building at 562 Fifth Ave in Manhattan. They bound and gagged the workers and took $25,000 worth of goods. He was released soon after the arrest. In May of 1931, at age 26, he was mysteriously gunned down by a passing sedan outside a bar in Upper Manhattan.

Agostino Murder Case, 1923

Scarsdale Slaying

Crime: Murder, Second Degree
Perpetrator: Nicola Agostino
Victim: John Piccino

crime of murder
Photo courtesy of the Westchester County Archives

Nicola Agostino and John Piccino worked on the grounds at the Fenimore Country Club in Scarsdale. (Fenimore was the predecessor to Fenway GC. It was founded in 1920 and reorganized in 1936, during the Great Depression, as Fenway.) They lived on the premises in rooms adjacent to and within the garage. The two men had an argument and, after the other workers were already asleep in their bunks, Agostino shot and killed Piccino. He was indicted and later convicted of murder in the second degree.

Flegenheimer Wanted Poster, 1933

Don’t Mess With the IRS

Crime: Federal Income Tax Violation
Perpetrator: Arthur Flegenheimer (aka Dutch Schultz, Arthur Schultz, George Schultz, Joseph Harmon, Charles Harmon)

Flegenheimer Wanted Poster, 1933
Photo courtesy of the Westchester County Historical Society

Bronx-born bootlegger Arthur Flegenheimer, best known as Dutch Schultz, allegedly amassed a $50 million fortune and hid it somewhere in New York’s Catskill Mountains (the town of Phoenicia is the best guess) prior to being gunned down in a New Jersey steakhouse in 1935 at age 33. In the years before his death, Schultz lived in Yonkers and Bronxville with his wife, Frances Flegenheimer. He beat a charge of income-tax fraud but, while hiding out for months prior to the trial, he lost much of his business to his New York rivals.

Related: A Look at Westchester County’s Prison System – and the People Inside It

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