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The Vicious Whyos Street Gang of New York

I've spent half a century (yikes) writing for radio and print—mostly print. I hope to be still tapping the keys as I take my last breath.

In the late 1860s, the Whyos gang began a reign of terror in Manhattan that lasted more than 20 years. They started out with simple thuggish crimes such as robberies, assaults, and killings and then progressed into the more “sophisticated” fields of extortion, prostitution, counterfeiting, and racketeering.

Manhattan’s slums were a breeding ground for violent street gangs such as the Whyos.

Manhattan’s slums were a breeding ground for violent street gangs such as the Whyos.

The Whyos Form

The Five Points area of Manhattan was a slum of epic nastiness in the middle of the 19th century. In 1842, Charles Dickens visited the area and wrote, “What place is this, to which the squalid street conducts us? A kind of square of leprous houses, some of which are attainable only by crazy wooden stairs without. What lies behind this tottering flight of steps? Let us go on again, and plunge into the Five Points ....”

The filth and squalor of the place nurtured the roots of violent gangs. Between 1866 and 1868, the New York Police Department tried to rid the Five Points of its worst elements. But, the remnants of broken-up gangs soon reformed among Irish immigrant criminals.

They would call to each other in the streets making the sound of a bird singing Why-Oh; hence the name.

The Whyos gathered members and strength and moved their criminal activities to a wider area encompassing most of Lower Manhattan. They were so vicious and powerful that anybody thinking about engaging in crime had to first get permission from the Whyos.

A rogue’s gallery of Whyo gangsters. The top row features (left to right) Baboon Connolly, Josh Hines, and Bull Hurley. The middle row is Clops Connolly, Dorsey Doyle, and Googy Corcaran. The bottom row shows Mike Lloyd, Piker Ryan, and Red Rocks Farrell.

The Whyos Headquarters

Members of the gang, when not engaged in some sort of mayhem, used to frequent a dive in the Bowery known appropriately as The Morgue. The owner boasted that the liquor he served had two purposes, to get the drinker soused quickly and to be used as an embalming fluid later.

It’s quoted in many places that The Morgue was the scene of more than 100 murders. Gunfights lasting an hour were apt to break out among gang members, but they were usually so plastered that a fatal bullet was likely to be accidental.

Other neighbourhood taverns had equally inviting names: Milligan’s Hell, McGurk’s Suicide Hall, and Chick Tricker’s Flea Bag were a few.

Piker Ryan’s Price List

One of the many bruisers that ran with the Whyos was a man known as Piker Ryan. He was a thug-for-hire to do whatever nasty work needed to be done by those with the cash to pay for his services.

In 1884, Piker Ryan was arrested for one of his many crimes. In his coat pocket police found a price list for the “disfigurements” he offered:

  • A simple punch in the face was available for two dollars;
  • Two black eyes cost four dollars;
  • Escalating levels of violence carried higher prices, so the tariff for a broken jaw and nose was $10;
  • Broken arms or legs had a value of $19; and,
  • What was euphemistically referred to as “doing the big job” came in at $100 (that’s about $2,500 in today’s money).

Co-Leading Dannys

Two Dannys co-led the gang for a while, Danny Lyons and. Danny Driscoll. Lyons ran a group of prostitutes when he wasn’t carrying out contract murders and assaults. He hired a famous hooker “Pretty” Kitty McGown away from her pimp, Joseph Quinn.

Mr. Quinn was displeased and a gunfight broke out, with Quinn turning out to be the loser. Lyons was tracked down, charged with murder, convicted, and hanged in the Tombs Prison in August 1888.

There is an alternative narrative about Dan Lyons’s demise put forward by author Robert Wilhelm. He says the Dan Lyons of Whyos infamy was shot and killed in a Five Points saloon in August 1887. Lyons was drunk and belligerent and when he was refused more booze pulled out his gun. The sober bar owner, Daniel Murphy, was quicker and his shot hit Lyons in the head.

Wilhelm says Joseph Quinn was indeed murdered by a Dan Lyons, but it was a different man with the same name. Somewhere along the line, the identities of two men were switched by a writer and subsequent chroniclers perpetuated the error.

Whatever the truth, Dan Lyons of the Whyos died in the late 1880s.

Two of Lyons’ stable of ladies were later in a Bowery pub toasting their late protector when a fight broke out between them. Gentle Maggie plunged a knife into the neck of Lizzie the Dove. As Lizzie lay on the floor, her life slipping away from her she is said to have pledged to Maggie that she would “meet you in hell and there scratch your eyes out.”

Danny Driscoll met the same fate as Danny Lyons. He got involved in a melee with Bridget “Beezy” Garrity and a man called John McCarty. Descriptions of the encounter are confusing but the important bit is that Bridget was shot and killed and Driscoll’s gun was the only one fired. Danny Driscoll was dispatched in January 1888 in The Tombs Prison.

The Tombs Prison where Danny Driscoll and many other street hoods met their fate.

The Tombs Prison where Danny Driscoll and many other street hoods met their fate.

The Whyos Final Days

With the two leaders dead and buried, the Whyos were weakened and vulnerable to the depredations of other vicious criminals.

Without strong leadership, the gang members started squabbling among themselves over the spoils of crime. Other gangs seeing the disarray swooped in to pick over the carcass. Also, the police had had enough of the Whyos and started to crack down on them.

The Five Points Gang was one of the groups that helped bring down the Whyos.

The Five Points Gang was one of the groups that helped bring down the Whyos.

This is where we meet Monk Eastman. He had the goal of picking up the pieces of the Whyos businesses in opium dens, gambling, and other rackets.

He cultivated the crooked politicians of Tammany Hall who saw to it that the police didn’t get too aggressive with his gang. And, if through some misfortune, a gang leader ended up in court, cash under the table saw to it that judges came down with favourable verdicts.

But eventually, Eastman became too uncontrollable for the compliant politicians and they stopped protecting him. He got a sentence of ten years in Sing Sing.

Eastman died as you would expect him to, shot by a disgruntled criminal accomplice in December 1920.

Monk Eastman.

Monk Eastman.

Bonus Factoids

  • One Whyo gang member, “Dandy” Johnny Dolan, had special boots made for him with ax blades embedded in the soles. These came in useful, once he had downed an adversary, for stomping on him. Dolan was hanged in The Tombs Prison in April 1876. He was 26.
  • Many other gangs infested New York in the 19th century. The Daybreak Boys were suspected of between 20 and 40 murders in the early 1850s. To join this gang prospective members had to kill someone. The Dead Rabbits gang was formed in the 1830s and specialized in “persuading” voters to cast their ballots for politicians they supported. They fought many street battles with their arch rivals, the Bowery Boys, who favoured the Know Nothing anti-immigrant party.
  • One of the habitués of the Lower Manhattan slums was Hell-Cat Maggie. She filed her front teeth to sharp points so as to inflict maximum damage on an opponent in a fight.
  • Despite being female, Gallus Mag (her real name is unknown) was the chief bouncer at the infamous Hole-in-the-Wall tavern in the Five Points. An imposing six feet tall, she walked among the patrons with a club to discourage drunks from getting disruptive. If a few belts from the bat didn’t quiet the drunk down Mag would bite off his ear before throwing him out. She kept her chewed-off trophies in pickle jars behind the bar.

Sources

  • “Wanna Be in Our Gang?” Robert McCrum, The Observer, November 24, 2002.
  • “7 Infamous Gangs of New York.” Evan Andrews, History Channel, June 4, 2013
  • Infamous New York.
  • “Sadie ‘The Goat’ Farrell – Queen of the Waterfront.” Joseph Bruno, Legends of America, undated.
  • “Word for Word / New York Gangs; The Dapper Don and Company Were a Bunch of Copycats.” Joe Sharkey, New York Times, May 3, 1998.

© 2018 Rupert Taylor

Comments

Fin from Barstow on May 05, 2018:

Good article with some nice details. I like the photos as well. You might be interested in "How the Other Half Lives" by jacob riis which talks about the poverty and such in new york that inspired some of the gangs...

good selection of photos and very informative trivia

Rupert Taylor (author) from Waterloo, Ontario, Canada on April 23, 2018:

Thanks Ralph, although I feel like I hardly scratched the surface of the topic. There were some truly evil people that sprang from the Manhattan slums.

Ralph Schwartz from Idaho Falls, Idaho on April 23, 2018:

An insightful look into the early days on the island of Manhattan, complete with colorful brigands, notorious thieves, and general rabble-rousers. You've summarized the events into a compact and easy to read narrative - thanks for sharing !

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