Prohibition Inwood: Gangland Slaying at Dyckman Street Speakeasy

The Daily Argus, May 12, 1931.
The Daily Argus, May 12, 1931.

Roy Herbert Sloane, the shrewd and engaging young man who talked his way out of Sing Sing last fall, was cut down by shotgun fire from an automobile as he left the Mad Dot Boat Club, a speakeasy at 251 Dyckman Street, at 1 o’clock this morning.  He died half an hour later.” (New York Evening Post, May 12, 1931)

Brooklyn Daily Eagle, May 12, 1931
Brooklyn Daily Eagle, May 12, 1931

The Mad Dot’s official mail number is 251 and is about two blocks from the river.  An ordinary store on the ground floor of a light brown apartment, its sign is painted on the windows.  Curtains everywhere about it explain to all its social nature.” (New York Times, May 13, 1931)

A blue-eyed handsome man

Before being blasted to shreds in an infamous Dyckman Street gangland hit, Roy Sloane had been a suave, even brilliant young man who could have enjoyed any number of well-paying careers.

Tall and handsome, with soft blue eyes, Sloane was educated at Columbia University.  Those who knew him described him as a driven, sometimes cunning young man who had grown up in an affluent and educated household.

His father, a Congregational Minister, did his best to provide a moral compass, while his mother, a well-known author and former Labor Investigator for the State Department, did her best to keep her son on the straight and narrow.

But in Prohibition Gotham, the seemingly endless piles of dirty money generated by rumrunners, racketeers and assorted gangsters proved an irresistible lure to Sloane and many of his generation.

Despite his parent’s best intentions, Roy had always been a troublemaker.

Roy Sloane's mother, Mrs. Anna Bogenholm Sloane.
Roy Sloane’s mother, Mrs. Anna Bogenholm Sloane.

His mother, a well-known writer of the day, hoped her son might follow in her footsteps, but her spawn had a much darker destiny in mind.

Simply put, Roy Sloane son was a sociopath.

The Daily Argus. May 12, 1931.
The Daily Argus. May 12, 1931.

A sociopath, who, in May of 1931, would find himself on the receiving end of a volley of shotgun blasts while exiting the Mad Dot Boat Club, a dingy Dyckman Street speakeasy, at the age of twenty-five.

The slippery genius

Years earlier, in July of 1926, Roy Sloane was caught behind the wheel of a stolen Nash automobile.  Inside his pockets were 246 car keys.  He was suspected in the theft and resale of dozens of cars.  At trial, evidence was also introduced that he had been charged with misuse of an automobile and of violating his parole.

Originally sentenced to ten years in New York’s Sing Sing Prison Sloane watched desperately from the inside as his sentence was extended; the result of both an attempted prison break and the discovery of brass knuckles in his cell.

Gloversville, New York Herald, February 26, 1931.
Gloversville, New York Herald, February 26, 1931.

Using the system to his own benefit, the former Columbia student began the study of law.

Acting as his own lawyer, he unbelievably succeeded in having his sentence overturned and walked out of the big house thirteen years early.

A free man, Sloane told reporters that prison had done him good and that he planned on continuing his legal studies on the outside.

But the slippery young legal eagle quickly resumed his life of crime.

Caught up again

On February 15, 1931, just months after being released from Sing Sing, Sloane once again found himself on the wrong side of the law—this time caught at the scene of a botched jewelry heist.

Trapped in the lobby of 562 Fifth Avenue he was arrested as one of a trio of thieves who brazenly stole $8,000 worth of diamonds from the firm of Karos and Stein

The case is simply this,” wrote one newspaper reporter. “A wholesale jewelry firm was robbed by three men.  An alarm was given and the building was quickly surrounded by police.  Sloane’s nervousness and misstatements when questioned with dozens of other persons in the lobby led to his arrest and subsequent identification as one of the bandit trio.”  (Morning Herald, February 26,1931)

Caught red-handed, Sloane seemed unfazed by his latest legal predicament. “After seeing the things that I have, life has no terrors for me,” he bragged. (Morning Herald, February 26,1931)

Sloane was soon released on  $20,000 bail following his arrest and vowed to act as his own attorney at trial.

With a cynical smile he informed the Herald reporter, “There’s nothing like personal experience when it comes to understanding the law.  I’m having my share of experience too, but if everything doesn’t come out all right, I have only myself to blame.”

Blood on the streets of Inwood

Yonkers Statesman, May 12, 1931.
Yonkers Statesman, May 12, 1931.

The night of his death, Sloane left his mother’s apartment at 547 West 123rd Street around seven o’clock.  Before departing, he told his mother that he intended to pick up $1,000 he had been promised to cover his legal expenses related to the jewelry heist

According to the New York Times,  “His movements during the next few hours are not entirely clear, but by midnight he was leaning against the Boat Club’s neat oak bar ordering drinks for his friends and constituents.   Some say that he arrived alone and others that he had escorted two young women.

From the accounts given by Frank Graeme, the bartender, and one or two customers, the police learned of the three young men who had been guests of the Boat Club most of the evening.  They were all stocky, their dark complexions set off by the grey of their clothes.  Just before Sloane walked in, one answered a telephone and reported to his companions that “he’ll be here in a minute.”   As if in answer to this prophet Sloane walked in. 

The four chatted for a time in a friendly sort of way, and then Sloane told the bartender to give the others “nothing stronger than beer.”    This was regarded as an obscure request, a subject for laughter. 

At about 1 o’clock am, Sloane and one companion stepped from the club’s neatly curtained doors to the street. 

251 Dyckman Street, March of 2013.
251 Dyckman Street, March of 2013.

As the two men came out—the second apparently being the “spotter” for the party—a maroon colored car started along the street in the direction of the ferry. As it went by the door opened and there were two loud reports, following in close succession.  Of the lot, Sloane received three slugs and the remainder went through the windows on either side of the club’s door.  The car gathered speed, the “spotter” disappeared and the two friends inside dashed out and away.”  (New York Times, May 13, 1931)

Sloane managed to stagger some 150 feet before collapsing on the sidewalk in front of 20 Seaman Avenue where he was found sprawled out on the ground in a pool of blood of his own blood by Patrolman John Peraglia.

The policeman had raced to the scene after hearing shots fired and had followed the blood trail to Sloane’s crumpled body.

Amazingly, Sloane was still alive.  But just barely.

Wheezing and sputtering a fine red mist, Sloane attempted to speak.  Perhaps he wanted to finger his killers before surely slipping away into the darkness.  A true gangster’s death.

The policeman raised Sloane’s head on his arm.  The dying youth attempted to say something and Peraglia bent closer to hear him,” The Yonkers Statesman reported.

But Sloane was too weak, his life was ebbing and he dropped back unable to utter anything but a gasp which carried no word.  He had been shot in the abdomen and in the thigh by shotgun slugs which tore the flesh in gaping wounds.” (Yonkers Statesman, May 12, 1931)

According to another newspaper account, Peraglia said Sloane gave him a slight smile before losing consciousness, “his pale features were flushed blood red and then faded to chalk as his life ebbed there on the sidewalk.” (New York Statesman, May 12, 1931)

The policeman quickly hustled the young convict into a taxicab for the short ride to the nearby Jewish Memorial Hospital, then located on Dyckman Street near the Hudson River.

Sloane was pronounced dead a half an hour later.

New York Times, May 13, 1931.
New York Times, May 13, 1931.


Inside Sloane’s pockets police found five dollars, a fake mustache, a phony automobile license under the name John McDermott of 530 Riverside Avenue, a bogus police badge, keys to a stolen Nash automobile found parked across the street (as a twenty year old Columbia University student Sloane had been busted in Mount Vernon for carrying a master set of keys used on Nash automobiles.  Sloane was a Nash man. )

Prohibition agents arriving on the Dyckman Street crime scene quickly arrested the Mad Dot Boat Club’s owner Jimmie Delucia and a bartender on charges of possessing liquor.

They also issued an alert for the maroon sedan, license plate number 2 L 5592, which had been seen speeding from the scene.

A mother’s denial

On hearing the news of her son’s death Anna Bogenholm Sloane, who had ironically penned a best seller on the proper upbringing of children, reportedly collapsed when informed that Roy had been killed.

The Daily Argus, May 12, 1931.
The Daily Argus, May 12, 1931.

Once composed, she seemed shocked, telling reporters her Roy was an automobile salesman who came home early every night.  He “was a model boy in every respect,” she told the New York Times. (May 13, 1931)

But of course that wasn’t the truth.  Roy’s fall from grace and outright criminality had begun years earlier.   Her son’s bloody death at the fiery end of an assassin’s shotgun couldn’t have come as a complete surprise.

A mystery unraveled

As to the motive for the killing itself, police had three theories:

1)   One of the three men from the speakeasy had been or felt insulted by Sloane and exacted his revenge.

2)   Sloane had been “put on the spot” by fellow gangsters who felt Sloane had cheated them of their share of recent spoils.

3)   Sloane had entered the liquor business and had been slain by rival racketeers.  (New York Daily Argus, May 12, 1931)

In December of 1931, during the trial of Sloane’s jewelry heist cohort, Harry Jacobs, the real reason for Sloane’s execution style murder was revealed.

Unlucky in crime, Sloane turned out to be unlucky in death as well.  His shooting had been a simple case of mistaken identity.

Vincent "Mad Dog" Coll
Vincent “Mad Dog” Coll

In court testimony, Jacobs asserted that the intended target was, in fact, Vincent “Mad Dog” Coll; A.K.A. the Harlem “baby Killer.”

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  1. There was another gangland shooting on Post Ave. in 1948 . Tommy Collentine came out of his building when a car pulled up two guys got out with machine guns. My Uncle who was walking down Post to go to work with Collentine, saw the killers who told him to run and don’t stop. Which of course he did. They then shot Collentine. It was never solved but in those days you didn’t talk.

  2. There is a book “Dark Harbor” by Nathan Ward, published by Farrar, Straus and Giroux that goes into detail about the Tommy Collentine shooting.

  3. My great great grandfather was the brother of Tommy Collentine’s father. I’m proud he was a tough character and sorry for his family but glad my branch went to the midwest!


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