Mollie/Molly Holbrook (1838-?) aka Hoey/Hoy
Widely acknowledged as the most notorious female thief in America from the 1860s through the 1880s. She was known to the nation’s police departments mainly as a pickpocket and shoplifter, but began her traceable career as a Clark Street “panel-room” brothel madam in Chicago, where clients were robbed while they were distracted by an accomplice hiding behind a partition.
Holbrook’s origins are unknown, as is her real name. Byrnes states that her maiden name was Williams and that she came from Boston’s West End, but without more information, that would be impossible to verify. She only came to public notice once she moved to Chicago and took up with Buck Holbrook, a street-tough thief. She was arrested under the name Mollie Holbrook several times in Chicago between 1868-1869 for operating a disorderly house.
In August 1869 (not 1871, as Byrnes asserts), Buck Holbrook went with a few of his pals to rob banks in western Illinois, but were captured and jailed in the town of Hennepin. The jail building was not secure, but a guard had been hired and told to shoot first and ask questions later. Holbrook and two other men managed to get past the buildings walls, but were spotted by the guard, who opened fire with a double-barrel shotgun. Holbrook was hit and dead before he hit the ground, his head and torso struck by seventy-eight pieces of buckshot. One of the others stopped and surrendered; the third was recaptured the next day.
Mollie came down from Chicago to retrieve the body of Holbrook, horribly disfigured. In Hennepin, she told those gathered around the body, “We all know that Buck was not on the square; but he was always a good and kind man to me.” Which is about as good an elegy that someone like Buck deserved. Mollie gave Holbrook a fine funeral in Chicago, attended by over a hundred of the city’s thieves, roughs, and prostitutes.
Mollie then took up with one James “Jimmy” Hoye, with whom she worked as a pickpocket. Hoye served as the “moll buzzer,” following Mollie into crowds and taking the goods that Mollie lifted as soon as the act was done–so that Mollie would never be caught with the evidence. She was arrested in New York State by a Chicago detective Ed Miller in early 1874; he foolishly attempted to bring her back via the Grand Trunk Railroad which runs partly through Canada. In Kingston, Ontario, she leapt off the train and sought protection from the police. Ed Miller had no requisition papers, so the Canadian official refused to hand her over. She later contrived to escape across the river to the United States. A few months later, former-Detective Miller–in an effort to regain his job– brought a woman to Chicago from Troy, New York, that he claimed was Mollie Holbrook–but was proven wrong.
By the early 1880s, Mary was working northeast cities as a pickpocket. She was arrested several times in Boston and New York, but either jumped bail or got off through the talents of her New York lawyers, Howe & Hummel. She took her stolen goods to the infamous New York fence, Marm Mandelbaum. In 1884 she was rearrested on one of the old charges and sentenced to five years at the prison on Blackwell’s island. During her court appearances, she appealed once more to Mandelbaum to provide legal assistance, but it was not forthcoming. Mollie took revenge by negotiating with New York’s District Attorney to offer testimony against Mrs. Mandelbaum–it was due to this pressure that Marm Mandelbaum was forced out of New York and retired to Hamilton, Ontario. According to the New York Times, Mollie also offered the DA information on Chief Byrnes extra-legal arrangements.
In September 1886, Mollie and Hoey were arrested in Cleveland, Ohio. Mollie was placed in the county jail. Using a pair of scissors and a hairpin, Mollie and an 18-year-old young male prisoner were able to remove a section of wall bricks and crawl to freedom; this occurred just days after the sheriff had boasted that no one had escaped from his jail.
After 1886, traces of Mollie Holbrook disappear. Rumors suggested that she and James Hoey left the United States and went to Europe.