Sophie Lyons at the Fair

Sophie Lyons at the Fair

We have in jail again one of whom perhaps a few here and in Detroit and Jackson have heard. Her name is Sophie Lyons, and she has been returned from the Work house for a new trial. She has already cost the county a large sum of money in the two trials she has had and the case may be taken to another court or perhaps not again prosecuted here. However it is to be hoped that no pains or money will be spared in giving this noted outlaw her just deserts. It would not be a bad reputation for Washtenaw County that it was a hard one for criminals.

— Ann Arbor Courier, July 13, 1883

Ann Arbor, 38 miles directly west of Detroit, is the seat of Washtenaw County and home to the University of Michigan. Founded in 1824 by East Coast land speculators, Ann Arbor has agricultural roots, but by the 1880s it was a flourishing town populated by well-to-do citizens.

Ann Arbor hosted the 33rd Washtenaw County Fair during the first week of October 1881. The fair gave farmers a place to display their harvest bounty and compete for cash prizes. “There were ninety entries of poultry, about sixty of sheep, 165 of fruit and sixty-five of grain and seeds.” Oxen, swine, horses, “fat cattle” and steer were also on display, along with flowers, butter, cheeses and sweetmeats. There was even a competition for the prettiest baby. Purses of between $40 and $150 were offered in a variety of horseraces. A hot air “balloon ascension” was another feature that drew in the crowds.

The atmosphere was festive despite the cold, rainy weather that dogged the fair during its first two days. However on the third day the weather improved and the crowds swelled. Harriet Cornwell, the elderly wife of a wealthy paper mill owner, attended the fair that Thursday.

Harriet was in the Floral Hall when a lady wearing a broad-brimmed hat with a veil stopped and asked her if she’d dropped her handkerchief. Harriet wasn’t sure but after checking, she discovered that she had. The woman offered to find it for her. Harriet wasn’t in good health and she gladly accepted the kind offer. The woman asked bystanders to move back so she could locate the hanky. After she located it and handed it to Harriet, she left so quickly she seemed to have vanished into thin air. Harriet didn’t even get a chance to thank the stranger for her kindness.

It wasn’t until after she got back home that Harriet noticed her gold watch and chain were missing. She thought the watch and chain might have been stolen at the fair, so she reported it to the police. She didn’t associate the loss with the veiled woman who’d retrieved her handkerchief.

Meanwhile, Superintendent Andrew Rogers of the Detroit Police was busy seizing packages sent to Sophie Lyons’ housekeeper. Many of the packages contained valuable watches and jewelry. Sophie told friends she’d gone to Cleveland to attend President Garfield’s funeral, but Rogers believed she’d really gone to put her talents as a pickpocket to use.

One of the packages the Detroit police intercepted was sent from Ann Arbor. It contained Harriet Cornwell’s gold watch and chain.

washtenaw court house 1877

Washtenaw County Court House, Ann Arbor, Michigan

Sophie was charged with “larceny from the person” for the theft of Harriet’s valuables. She was placed on trial at the Washtenaw County Court House.

The prosecutors had to prove Sophie was at the fair in Ann Arbor on the day the watch and chain were stolen. This was difficult because she wore a hat and veil wherever she went, including in the courtroom during her trials. Some witnesses were certain they had seen her in Ann Arbor. Others  weren’t so sure. Her defense attorneys had witnesses who knew her and testified that she’d been in Detroit the day the watch was stolen.

Sophie veiled hat

Sophie Lyons in one of her unusual veiled hats; 1887 mugshot photo taken in St. Louis, MO

According to the prosecutor, when the judge ordered Sophie to show her face to a witness, she “sprang like a panther, tore her wrappings from her head and face and rushed to the witness, thrusting her face close up” to the witness’s face. She kept her back to the courtroom and immediately replaced the hat and veil after the witness got a look at her.

Sophie was volatile in court — at times she cried, asking who would care for her children if she went to prison. Other times she threatened violence against prosecution witnesses. She had a sharp tongue and seemed to enjoy using it.

Theresa Lewis was called as a witness, but her credibility was damaged when her role as a confidential informant for the police was revealed.

Sophie’s trials in Ann Arbor attracted large crowds. Many attended hoping to hear her fling insults at Theresa or even see the two women brawling with one another. Sophie accused Theresa of stealing things from her home while she’d been a tenant. At one point the judge ordered Sophie and Theresa to stand next to each other. Sophie took the opportunity to bash into Theresa, sending her flying across the courtroom.

DeHoCo

Stereoview of cells and passage in the Detroit House of Corrections, ca. 1880; NYPL

The prosecution prevailed and Sophie was convicted of stealing Harriet’s watch and chain in March 1882. She was sent to the Detroit House of Correction but released seven months later when the Michigan Supreme Court reversed the conviction. She was was tried again and convicted a second time, in February 1883, and sent to the DeHoCo again. The Supreme Court overturned her second conviction in July 1883.

Her money exhausted and her health poor after two incarcerations, she begged the judge to drop the charges, but he refused. Her final trial in Ann Arbor was held in March 1884. She was found not guilty at the third trial, however her legal troubles weren’t over yet.

She was immediately held in Detroit on charges related to pickpocketing in Cleveland. However by then Theresa, who was also an important witness in that case, was suffering from cancer. After many postponements, the charges were dropped when Theresa died in May 1886. Sophie then left Detroit and headed to other large cities where her face was less well known.

sohpie lyons author marked

Sophie Lyons, author photo, ca. 1913

Thomas Byrnes, Chief of Detectives in New York City, published Professional Criminals of America in 1886. Byrnes described the 204 criminals he considered to be the most dangerous individuals in America. Sophie was one of only ­­­18 women to make the cut. He noted in her bio that she had been recently “convicted at Ann Harbor, Michigan” but his information was already out of date.

Sophie spent the next 20 years shoplifting, pickpocketing, robbing banks and blackmailing people all over the Midwest (except Michigan), the East Coast, Canada and Europe, but ultimately she returned to her home in Detroit. By the early 20th century Sophie claimed she’d reformed and even published a memoir, titled Why Crime Does Not Pay. Though she had given up crime, her substantial fortune came almost entirely from her earlier criminal activities and the irony of her book’s title was certainly deliberate.

If Sophie ever made another visit to Ann Arbor after 1884, she kept it quiet. No doubt she wanted to avoid the town where she was put on trial three times for the same crime — it was a record for her and not one she would have bragged about.

She died in 1924 at Grace Hospital after collapsing of a stroke in her home. Her cremains were buried next to those of her favorite child, Carleton Mason (who spent most of his life in Seattle, steering clear of his mother and her notorious reputation) at Detroit’s Woodmere Cemetery.

Featured Photo: mugshot of Sophie Lyons from Professional Criminals of America by Thomas Byrnes, 1886.

A Noted Woman Outlaw

A Noted Woman Outlaw

Sophie Lyons, the woman who indulges in aliases, pistols, morphine, etc., was released from arrest yesterday, the doctors failing to agree on her insanity.

— Detroit Free Press, May 25, 1881

For years the name “Sophie Lyons” raised the hackles of policemen throughout the world. Sophie was particularly unpopular in southeastern Michigan, where she was tried three times for pickpocketing in the early 1880s.

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Pre-1876 drawing of Sophie based on her now-lost mugshot photograph

Her story began in New York City on Christmas Eve 1847, when Sophia Elkin was born to German-Jewish immigrant parents. The youngest of three children, she was taught to steal during childhood by her family, who were part of the Gotham criminal underworld. At the age of 12 she served a prison term for burglary at the New York House of Refuge on Randall’s Island, off the coast of Manhattan.

After her release from prison she took her mother’s maiden name, Levy, and worked for Fredericka “Marm” Mandelbaum, an infamous New York City fence, who helped polish Sophie’s pickpocketing and shoplifting skills. Her first marriage to a thief named Maurie Harris was short-lived. By the age of 18 Sophie was married to her second husband, Edward “Ned” Lyons, a notorious bank robber. All four of Sophie’s husbands and most of her many lovers were criminals.

By the late 1870s Sophie had split with Ned and moved to Michigan, partly due to its proximity to Canada, which at the time had no extradition treaty with the United States. There she operated under several aliases, including Kate Loranger and Harriet Smith. The Detroit police soon figured out her true identity and found that she’d learned her craft from New York City experts and had an escape from Sing Sing under her belt.

She tried to commit suicide in 1877 while she was held in the Detroit jail on a shoplifting charge. At the time she was addicted to morphine and was going through painful withdrawal symptoms. While she was in court awaiting a hearing, she violently attacked another prisoner who had insulted her.

Andrew Rogers, Superintendent of the Detroit Police, breathed a sigh of relief when Sophie left Detroit, but by 1880 she’d returned. In March 1881 she tried to shoot George Hendrie, the wealthy owner of the Detroit City Railway. She claimed the married Hendrie had fathered a child with her and she demanded money from him to keep the matter quiet. Hendrie refused to succumb to her blackmail attempts so she confronted him at his office, pistol in hand. Fortunately for Hendrie, she was a lousy shot and the bullet missed its mark.

Andrew Rogers

Andrew Rogers, ca. 1905, Detroit Historical Society

Rogers suspected that Sophie was pickpocketing and shoplifting on his patch again, but she was so clever that it was difficult to get evidence against her, so he resorted to an unusual tactic. He hired a poor Detroit widow, Theresa Lewis, who was desperate for cash, to work as his confidential informant. Theresa’s job was to ingratiate herself with Sophie, spy on her and gather evidence against her to be shared with Rogers and one other trusted police officer.

During the summer of 1881 Theresa went to Sophie’s Detroit house at 23rd and Fort streets and offered to read the bible with her. Sophie had no interest in the bible but she allowed Theresa to stay as a tenant in her home. Theresa moved in and began to spy on the household. She reported her discoveries back to Rogers.

Sophie left town to attend the funeral of President James Garfield in Cleveland, Ohio, on September 21, 1881. Theresa told Rogers that Sophie’s housekeeper, Sarah Brew, began to receive many packages sent from out of town by a “Sarah Smith” after Sophie left. Theresa kept some of the wrappings from the packages and gave them to the police.

Garfield funeral Cleveland

Crowds in Cleveland for the Garfield funeral

Rogers suspected that “Sarah Smith” was actually Sophie and that the packages contained items stolen by her while she was out of town, so he instructed his trusted officer to intercept any packages at the post office that were addressed to Sarah Brew.

The Garfield funeral, with its massive crowds, provided abundant prospects for pickpockets, but it wasn’t the only situation that was ripe with opportunities. County fairs, with their large crowds and many distractions, offered exceptional hunting grounds for pickpockets looking to practice their craft. And since the fairs were often held in smaller communities, people were less likely to be on their guard than in the crowded shopping districts of big cities.

The next time Sophie appeared on the radar of Superintendent Rogers, she’d been at a fair in Ann Arbor, Michigan.

Next post: Sophie Lyons Goes to the Fair

Featured photo: Sophie Lyons, CDV by James Alba Bostwick; National Portrait Gallery, Smithsonian Institution; gift of Pinkerton’s, Inc.

Two Chucks Make One

Two Chucks Make One

Pickpockets Arrested…The Mayor has also received information that two men, named John North, Jr., alias Smith, alias Musgrave, alias “Big Chucks,” and John Thompson, alias “Little Chucks,” professional pickpockets, were in the city, loitering and sleeping about the Neptune engine house. They were also arrested and committed thirty days each for vagrancy. On the person of “Little Chucks” was found a small memorandum book, in which he had a list of the county fairs in Ohio, where he proposed to follow his calling.

Pittsburgh Daily Post (Pittsburgh, Pennsylvania), September 6, 1858

The arrest in Pittsburgh of two men dubbed with the “Chucks” moniker was reported as far away Washington, D.C., where they were described as “two noted Philadelphia pickpockets.” Evidently the men planned to visit county fairs in the mid west — fertile hunting grounds for prospective victims with full pocket books and distracted brains.

The following year John Keeley, better known as “Little Chucks” was arrested in Philadelphia after he was chased from a church building by a police officer. He was sent to jail for vagrancy and attempted pickpocketing. He was also accused of “riot and malicious mischief.” Less than two months later, Thomas W. North, also known as “Big Chucks,” was arrested in Baltimore, along with another man, for knocking down and robbing Gibson M. Nelson. Mr. Nelson subsequently died as a result of the injuries he sustained during the robbery.

John North, alias Keely, was arrested in March 1861, in Camden, New Jersey, for pickpocketing. Only a few days previously he had been released after a two year stay in Philadelphia’s Eastern State Penitentiary for the same offense. The news report about his release mentioned that he was also called “Little Chucks.”

Smart nineteenth century criminals kept police busy with a bewildering array of aliases and nicknames. “Big Chucks” was called John or Thomas North, or John Smith or John Musgrave. “Little Chucks” was known by the first name John and the surnames North, Thompson or Keeley. Several newspapers reported that “Big Chucks”and “Little Chucks” were two criminals who often worked together.

Were the Chucks actually two men, as the newspapers claimed? Photographic evidence argues for a different conclusion.

big chucks backCrudely scratched in the metal plate on the reverse of an ambrotype photograph from the St. Louis Rogues’ Gallery are the words “Big Chucks alias Daly.” The photo is undated but it was likely made around 1860. A photograph made by Samuel G. Szabó shows a man identified as “John McNauth alias Keely alias little Chucks Pick Pocket.” Szabó was a Hungarian photographer who traveled around America photographing rogues’ galleries in various police departments, including those in St. Louis, Philadelphia and Baltimore, between 1857 and 1861. His reasons for doing this are unknown, however he compiled an album of prints from his negatives. The album survived and was donated to The Metropolitan Museum of Art in 2005.

I’m convinced that the man wearing the fabulous top hat in the Met photo is the same man, shown hatless, in the St. Louis photo. It’s possible they were brothers who had remarkably similar hair and facial features but if so, it’s likely that detail would have been commented on in the news, but it wasn’t.

Why was it reported that “Big Chucks” and “Little Chucks” were two people? Like any accomplished criminal, he wanted to keep the police guessing about his identity. If they thought they were chasing not one man but two it was all the more confusing! So he varied his moniker and, when he worked with another pickpocket, suggested to the partner that he also use one of the “Chucks” sobriquets. As long as he wasn’t photographed, who would ever know?

Once police got his photograph and circulated it around, the game was up. This was precisely the reason rogues’ galleries were started in St. Louis and New York City and were soon in popular demand in other large American cities.

Who was he really? Based on most of his aliases he was probably Irish or the child of Irish immigrants, but we’ll never know for sure.

Featured photos: “Big Chucks,” Missouri History Museum, and “Little Chucks,” The Metropolitan Museum of Art.

Life Savings Larceny

Life Savings Larceny

It is a grave error for magistrate and justices of the peace to permit pickpockets [to] escape conviction. What is worse, such leniency is frequently due to the influence of the pickpockets with the minor judiciary who discharge them.

— Judge John Monaghan, quoted in The Philadelphia Inquirer, August 5, 1920

Trifim Trochuk, a 37-year-old Russian immigrant, got on the Second Street trolley to ride to Philadelphia’s Washington Avenue Wharf on July 17, 1920. At the wharf he planned to board the steamship Haverford to sail back to his Russian homeland. He’d worked for the last six years as a dishwasher in a restaurant in order to save up enough money to return to Russia and bring his wife and children to America. His life savings, $867 in dollars and 600 Russian rubles, was in his hip pocket.

A young woman boarded the trolley and Trifim generously got up to give her his seat. As he did so, a man who had boarded with the woman jostled him and Trifim felt a hand reach into his hip pocket. He checked his pocket and panicked when he realized his money was gone. He shouted that he’d been robbed, then he noticed a roll of banknotes in the lap of the woman to whom he’d given his seat. She was trying to hide the notes with her handkerchief.

Ida Weiner_back_marked

Back side of Ida’s Bertillon card.

The man and woman, Harry Stoll, alias Dahl or Goodman, and Ida Wergna, alias Weiner, were arrested on suspicion of being pickpockets when the trolley reached its stop. The couple denied knowing each other, however they were tried together two weeks later. After one “stubborn juror,” who thought he needed to ask more questions and hear more witnesses, was convinced to change his vote, Harry and Ida were convicted of grand larceny.

There’s no record of whether or not Trifim got his money back.

Harry boasted of being arrested multiple times in New York and Philadelphia for pickpocketing, claiming he’d never been convicted. Not so lucky this time, he was sentenced to a minimum of two years at the infamous Eastern State Penitentiary by Judge Monaghan. Ida, who confessed to the judge about her role in the crime, was sentenced to eighteen months in Moyamensing Prison.

TrifimAccording to Trifim’s 1942 naturalization record, he never made the trip back to Russia where his four children still lived. Trifim’s wife, Uliana, died in Russia and he never remarried.

Featured photo: Bertillon card of Ida Wergna. Collection of the author.

Naturalization record of Trofim Trochuk: Massachusetts, State and Federal Naturalization Records, 1798-1950.

Angry in Omaha

Angry in Omaha

Minnie Bradley was arrested on the evening of December 11, 1902, and charged with “larceny from the person” or pickpocketing. Someone from the Midway Saloon, a well-known dance hall and whorehouse owned by several notorious Omaha crime bosses, offered to pay her $25 bond. Before she was released, W. H. Breiter showed up at the police station and identified Minnie as the person who had robbed him earlier that evening. Minnie offered Breiter $5 to drop the charge, but he refused, so she spent the night in jail.

Described in the newspaper as a “traveler,” Breiter had been “strolling about” near the Tenth street viaduct in Omaha, Nebraska. He told police that a woman appeared out of the darkness and demanded his money. He claimed he handed it over to her.

The next day Minnie appeared before Police Judge Louis Berka. The judge decided she could stand for trial for the Breiter hold up, but he offered her an alternative — if she left Omaha the charges against her would be dropped. She chose to leave rather than face a trial, but first the police took her mugshot to guarantee that all Omaha police officers would be familiar with her face, in case she was tempted to return.

judge-Berka

Judge Louis Berka. Find-A-Grave.

Minnie’s 1901 mugshot is unusual for the amount of emotion she displayed. She has her arms crossed and it’s obvious that she’s angry and unwilling to look at the camera, or maybe she looked away just before the shutter was released. Her occupation was listed as “prostitute” and her home, at 116 North Eleventh Street, was around the corner from the Midway.

Breiter’s story about Minnie robbing him doesn’t really add up. It’s unlikely that a lone woman would rob a man outdoors in a deserted spot at night. It’s possible that Breiter was a client who didn’t want it known that he visited a prostitute, particularly an African-American prostitute. He might have refused to pay, so she took what he owed her.

Minnie returned to Omaha in 1904 and made two more appearances in police court before Judge Berka. The first, in March 1904, was as witness against a man named William Warwick, who was accused of assaulting her. The two had gotten into a heated argument when he bragged to her that, due to his light complexion, he often passed as a white man during his travels out west. He also mentioned that he had been in the company of two white women the previous evening. Minnie said William should show more respect for his race and reminded him that his mother was a black woman. His response was to punch her. Judge Berka sentenced him to 30 days in jail.

Two months later, in May 1904, Minnie was the defendant in a case of assault and battery brought against her by an African-American woman named Annie Curtis. Annie was drunk and her behavior was violent — an argument broke out between the two women. Minnie claimed Annie was on the verge of throwing a phonograph at her when bystanders intervened. Annie claimed Minnie threw a brick at her, which Minnie denied. The outcome of the case was not reported.

Minnie slipped out of the news after 1904, but her mugshot leaves little doubt that she was a force to be reckoned with.

Featured photo: Minnie Bradley’s 1902 mugshot. Collection of the Nebraska State Historical Society.

Fainting Bertha

Fainting Bertha

She was an expert pickpocket who would steal a man’s diamond stickpin, using her well-known fainting trick, without batting an eye. But she was also mentally ill, suffering periodic bouts of insanity so intense that it was impossible for doctors or hospital attendants to control her. In the grip of one of these attacks, which sometimes occurred at night, she had been known to break every window she could reach while screaming profanities at the top of her lungs. Her mood swings were intense — she was calm one moment and crying hysterically the next. By July 1911, officials in Nebraska were faced with the vexing question of what to do with “Fainting Bertha” Liebbeke.

Bertha was born in Council Bluffs, Iowa, in March 1880 to William and Mary Liebbeke. William was a cobbler and an immigrant to the United States from Germany. Mary was born in Switzerland. Bertha’s parents met and married in Pottawattamie, Iowa in 1870. The Liebbekes had nine children and seven of them, including Bertha, lived to adulthood. William died in 1896.

Soon after her father’s death Bertha was diagnosed with Saint Vitus Dance (now called Sydenham’s chorea), an infectious disease that results in uncontrollable twitching and jerking movements of the victim’s face, hands and feet. Her diagnosis was likely what caused her to be sent to the Iowa Institution for Feeble-Minded Children in Glenwood. Possibly due to age restrictions she was transferred to the Iowa State Hospital for the Insane in Clarinda, where she remained for less than a year.

Iowa State Hospital for the Insane in Clarinda

Iowa State Hospital for the Insane, Clarinda, Iowa.

Between hospitalizations Bertha claimed she was seduced by a man named Gunther who schooled her in the art of “larceny from the person.” Despite her psychiatric problems, she was an excellent student. Not only was she good at getting the goods, she developed a unique approach to her profession, taking full advantage of her blond-haired, blue-eyed good looks and stylish appearance. Bertha would get into a crowd of people and swoon. The gallant gentleman who came to her rescue by catching her got a reward he wasn’t expecting — his pockets were picked. It was done so adeptly that most didn’t realize their loss until Bertha was long gone.

Bertha became notorious. She took trains to all the big midwestern cities, robbing train conductors and passengers along the way. She not only robbed individuals, she used her nimble fingers to steal from large department stores, such as Marshall Field & Co., in Chicago. Her photo was said to be in every rogues’ gallery in the Midwest by the early 1900s. It was reported that three times she had plans to marry, but the engagements were broken when she couldn’t stop thieving. Despite all that, she looked pleased as punch to be photographed by the Nebraska State Penitentiary, as inmate #5693, for her undated mugshot.

bertha-liebbeke-notorious-pickpocket-in-il-ks-ia-mo-and-ne-fainting-bertha-stumbled-into-men-fainted-and-robbed-them2

Bertha Liebbeke, undated mugshot. Collection of the Nebraska State Histrical Society.

Unfortunately for hospital and prison officials, Bertha was not only good at stealing cash, watches, furs and jewelry, she had a talent for lifting keys and picking locks. By 1907, she’d been housed in seven separate Midwest penitentiaries and asylums and she’d escaped a dozen times from those institutions. She’d attempted suicide at least once. Back and forth between hospital and penitentiary she went. No one wanted her, but the question of what to do with her remained.

She was sent to the Asylum for the Chronic Insane in Hastings, Nebraska. At Hastings, three physicians from the Nebraska State Insanity Board examined her as part of a report to the governor, Chester Aldrich, in 1911. The following description of Bertha was part of their report.

The evidence (is) that she has delusions or hallucinations as shown by her talking to imaginary persons and having the sensation of insects creeping under the skin. Immediately after physicians left her she became violent, which is a daily occurrence, running up and down the hall, bewailing her condition and position, running from one room to another to evade the physicians and berating them because of her belief that they would not look after her welfare.

The doctors weren’t sure of whether or not Bertha was insane, but they were unanimous in their opinion that she needed to be in a hospital, not a prison. The governor disagreed and sent her back to the Nebraska State Penitentiary to finish her latest sentence, specifying that “special quarters” be provided for her.

After her release from the penitentiary, in 1913, Reverend Charles W. Savidge of the People’s Church in Omaha offered her a home in the church. A safe room was prepared for her and someone from the congregation was available to be with her at all times. The congregation prayed for her and she renounced her bad ways. With the help of religion, Bertha’s “modern devils” might be cast out! The experiment didn’t work and the congregation gave up on her. By 1914 she was in custody in Milwaukee on a charge of vagrancy.

She was sent to the Lincoln State Hospital For Insane in Yankee Hill, Nebraska. She fell out of the news until 1919, when she attacked a nurse, throwing formaldehyde at the woman’s face and partially blinding her. We can only guess at what treatments Bertha endured in an effort to control her violent outbursts. She lived in the asylum for over 20 years and died there on May 5, 1939.

Her obituary in the Lincoln Evening Journal noted, “When arrested she would readily admit what she had done, and would gloat over men being easy marks. At the hospital it was reported that she had been a very difficult patient, and had caused the authorities much trouble.”

Featured photo: Bertha Liebbeke, carte de visite mugshot. Collection of the Nebraska State Historical Society.

Alias Dorsey Doyle

Alias Dorsey Doyle

When a federal census worker counted his family in 1880, George J. Doyle lived with his widowed father, John, and four siblings in the poverty-stricken Five Points section of lower Manhattan. The Doyle family’s tenement, located at 86 Mulberry Street, housed 19 families, 68 souls total, all with Irish roots. The building probably had six or seven apartments, no indoor plumbing and was less than a block from Mulberry Bend — one of the most dangerous areas in the slum-infested Five Points. George, soon to be known by the nickname “Dorsey,” was 14. He and his younger sister, Katie, were still in school while the rest of the family worked at low-paying jobs.

At the age of 14 Dorsey Doyle was likely already sharpening his skills as a pickpocket and readying himself for life as a gang member and career criminal.

Dorsey Doyle prison record

Description of George J. “Dorsey” Doyle, New York Sing Sing Prison Admission Register. New York State Archives; Albany, New York; Box 8; Vol. 23.

In 1887, when he was 21, Dorsey pleaded guilty to robbing a man of his watch and chain on the Manhattan side of the Brooklyn Bridge. He was sentenced to two years and three months in Sing Sing Prison. The prison entry for him lists six scars — most of them on his face — a testament to a life of violence, despite his youth. Sing Sing was known for whippings, solitary confinement, poor rations and a requirement of total silence from inmates. Rehabilitation for prisoners was decades in the future and many tried to escape, attempted suicide or went insane. Dorsey emerged from Sing Sing a full-blown, hardened criminal.

Dorsey was a member of the Whyos, a gang of Five Points Irish mobsters that hit its peak in the late 1870s and 1880s. While earlier New York criminal gangs spent most of their time fighting each other, the Whyos had the entrepreneurial spirit. Naturally they were involved in general thuggery, but they added extortion, prostitution and murder for hire to their menu of criminal activities. They were rumored to have a price list for the criminal services they supplied, ranging from $1 (punching) to $100 and up (“doing the big job”). By 1888, four of the Whyos members had been convicted of murder and hanged at the Tombs jail in lower Manhattan.

After his release from Sing Sing, Dorsey branched out from New York City and, in 1893, earned a three-year stay for grand larceny at the infamous Eastern State Penitentiary in Philadelphia. (Al Capone did a year at “ESP” in 1929.) By 1895 Dorsey’s flourishing career earned him spot #521 in Chief Inspector Thomas Byrnes new edition of his book, Professional Criminals of America. Byrnes described him as “well known throughout the eastern country, as he follows the races, fairs, etc.”

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Dorsey Doyle, May 1887; Professional Criminals Of America (1895) by Thomas Byrnes.

After an unsuccessful attempt, in 1898, at robbing a passenger of a gold watch and chain on a Broadway cable car in New York City (Dorsey shot at the policeman who eventually caught him) he received a second sojourn at Sing Sing. Shortly after his second release from Sing Sing, he and three other men were observed trying to pick pockets on an electric car in Manhattan. A mad chase by police ensued during which he jumped off the moving car and was the only man captured. He was convicted of attempted grand larceny and sentenced to Sing Sing for the third time!

At the turn of the twentieth century, with his Whyos pals dead or in prison and with a face that was well known to the New York police, Dorsey moved west. In 1908 he was arrested with another man for lifting a diamond stud off a man boarding a train in Wilkes-Barre, Pennsylvania. When he was arrested in Pittsburgh in 1915, the newspaper described him as “John Dempsey, alias Dorsey Doyle, aged 50, of Toledo.” He was one of a “mob” of clever pickpockets, all of them younger than Dorsey.

Fifty is ancient for a pickpocket — a skill necessitating quick reactions, nimble fingers and fast feet. Dorsey was never mentioned in the news after 1915, so he may have retired from crime and led a quiet, law-abiding life in Ohio. The days of the Irish gangs of New York were, after all, long gone, and no one, even a notorious criminal, wanted to risk a fourth stretch in Sing Sing.

Featured photo: Dorsey Doyle, carte de visite mugshot, circa 1892, by John Rosch. Collection of the author.