It’s a classic American success story. Fredericka Mandelbaum arrived in the U.S. as a penniless immigrant and built a cutting-edge, multi-million dollar business from scratch. The twist? “Ma” Mandelbaum ran a criminal empire, which she launched by gathering freelance thieves into a profitable network.

To launder the take, Mrs. Mandelbaum (as one must call her) became one of the biggest fences in New York, and eventually began masterminding bank robberies. At the same time, she turned herself into a philanthropist and political hostess, protecting her web of business interests by funding a major political machine. 

No, this isn’t a pastiche of modern news stories. Fredericka Mandelbaum arrived in New York in 1850 and reached the height of her influence in the 1870s and early 1880s. Yet when I read The Talented Mrs. Mandelbaum, Margalit Fox’s biography of the grande dame of 19^th century New York crime, I kept hearing 21^st century echoes. Allegations that a disproportionate number of immigrants are criminals, often refuted but still in the headlines. Stories about business leaders funding politicians to leverage their interests. 

These echoes are the first thing that struck me about Fox’s romp of a book—which is a great read—but there’s something else.

When a new District Attorney finally arrested Mrs. Mandelbaum, she posted bail and fled. Despite her wealth, Ma Mandelbaum didn’t disappear to one of the cultural capitals of Europe or even to the wilds of the Wild West, but to rough-and-tumble Hamilton, Ontario, about an hour down the highway from Toronto, where I live. There she rather grumpily lived out the rest of her life, reduced to running a Ladies’ and Children’s Underwear emporium before dying in 1894.

My friend Sheila moved to Hamilton a few years ago and we go on walks when I visit. After I read the book, we decided to take a walk around Mrs. Mandelbaum’s Hamilton, from the site of her underwear emporium to her two known residences, her synagogue, the former police headquarters. We thought it would be fun exploring the turn-of-another-century Hamilton, our route extrapolated from old city directories. 

Then the time came, and we found something entirely unexpected. 

But first, the book.

Mrs. Mandelbaum, the motherly criminal

Margalit Fox made her name writing obituaries for The New York Times, and since leaving, she’s published four books of non-fiction. In The Talented Mrs. Mandelbaum, she shows off her own talent for research. A criminal wasn’t going to leave diaries or financial records, so Fox mined the era’s flamboyantly-written newspapers and several tell-all books by Mrs. Mandelbaum’s contemporaries. They’re far from reliable sources, but taken with a grain of salt, they allow Fox to write a social history of crime in late 19^th century New York—and one centred on female criminals. 

Starting in the 1840s, New York Democrats’ Tammany Hall political machine employed ward heelers who got out the vote on election day by muscling voters toward the polls. Even before Mrs. Mandelbaum’s time, the muscle included a fractious crew of women. Fox quotes historian Alexander B. Callow Jr., who names several New York women known to the 19^th century, all of them “specialists in election-day mayhem.”

“Gallus Mag, who supported her skirts with suspenders, was a mean six-foot female who, armed with a pistol and a club, was employed as a bouncer at a dive called the Hole-in-the-Wall. Sadie the Goat, a prostitute and all-around rough-and-tumble fighter, ran with the Charlton Street Gang, a group of river pirates. She won her nickname by the way she would lower her head and butt like a goat in a fight… 

“Hell-Cat Maggie looked like an enraged tiger. Her teeth were filed to points and over her fingers she wore sharp brass spikes. Even the bravest of men lost their poise when she charged screaming into a polling place. (In a celebrated fight, she bit off the ear of Sadie the Goat.) The huge and violent Battle Annie, ‘the sweetheart of Hell’s Kitchen,’ was a terrifying bully. She commanded a gang of ferocious Amazons called the Battle Row Ladies Social and Athletic Club.”

Fredericka Weisner was born in 1825 into a far less dramatic family of Jewish peddlers in the town of Kassel, now part of Germany. When she was 23, she married another peddler, Wolf Israel Mandelbaum, who appears in Fox’s book as a mild Type B husband, with whom she had five children. Despite scant education, Fredericka was the brains of the family, and after emigrating to the U.S. in 1850, she didn’t last long behind the handles of the pushcart she and Wolf initially hauled through the streets of New York, selling cheap goods.

Instead, Fredericka’s attention was drawn to the far more profitable trade of pickpocketing. Profitable but largely disorganized—at least until “Ma” Mandelbaum stepped in and began to employ the local ragamuffins, creating a network of street-level thieves. In Fox’s telling, Mrs. Mandelbaum was a brilliant organizer, a natural businesswoman who, over more than 20 years, turned the raucous criminal underworld of New York into an efficient machine. 

It was call the Gilded Age, and the pickings were rich

Born more recently, Fredericka Mandelbaum might have used her talents to found a world-class corporation. Yet being a woman and a Jew, she was barred from legitimate enterprises. Fox is excellent in ferreting out the vocabulary of the 19^thcentury underworld she inhabited instead, introducing pickpockets known as “carbuzzers” who plied their trade on streetcars and omnibuses, “groaners” who stole money during church services, and the “files” who used small knives to slice open pockets. 

Mrs. Mandelbaum got her start by buying and re-selling scavenged and stolen goods brought to her pushcart by groaners and files, then apprenticed herself to a famous fence, “General” Abe Greenthal.

Under his tutelage, Ma Mandelbaum learned how to appraise luxury goods and how to seel them afterward at an excellent profit, keeping the lion’s share of the profits for herself. Once she had the capital, she opened her own store, legitimate on its face, but with a secret back room where stolen goods were processed. 

In the end, Mrs. Mandelbaum ran such a wide-ranging network of thieves that she grew both rich and influential. In elaborate dinners at her home, she welcomed crooked Tammany Hall Democrats and high-level New York City police, delivering pay-offs to ensure they would blink at her schemes. 

At least until newly-minted D.A. Peter Olney stepped in and arrested her, following a long period of surveillance by Gustave Frank and his Pinkerton detectives. 

Writes Fox, “On the morning of Tuesday, July 22, 1884, Frank and three fellow agents burst into Fredericka’s shop. The safe was opened, the jewels spilled out, Frank urged her to come clean and Fredericka socked him in the face.”

Yet she could still call in favours. When she went to trial, the judge found it in him to grant bail, and the now-widowed Mrs. Mandelbaum fled to Canada.

Not that everything changed

A little online research showed that Mrs. Mandelbaum’s Ladies’ and Children’s Underwear emporium was located at 70 King Street West in downtown Hamilton. She worked behind the counter, attended the Anshe Sholem Temple on Hughson Street South and remained close to her adult children. One of her sons ran a tobacconist’s shop a few doors away on King Street, while one of her daughters visited frequently from New York, carrying letters from friends and former colleagues.

Maybe more than letters. Her daughter arrived with trunks and suitcases bulging with clothes, not all of which seemed to leave the country with her. Competitors often grumbled that Mrs. Mandelbaum was somehow able to undercut them on the price of ladies’ underwear, although customs officers were never able to catch her daughter smuggling. Meanwhile, “Ma” Mandelbaum lived on Hughson Street near the synagogue before moving to Victoria Avenue, where she died.

Noting down the addresses, I began to plan the walk Sheila and I would take. 

One slight problem. A look at modern maps showed that all of these buildings have been torn down. The Anshe Sholem Temple still exists, but in a different location, and the Hughson Street site is now occupied by a Roman Catholic parish church. Hamilton’s City Hall sits where Mrs. Mandelbaum’s emporium once stood, and neither of her houses remains.  

Sheila and I were forced to pivot. We decided to walk past City Hall, nod toward the approximate site of Mrs. Mandelbaum’s underwear emporium, then head to an exhibit of paintings by an early female Impressionist painter on display at the Hamilton Art Gallery.

I tend to go down online rabbit holes. As we walked through Hamilton’s downtown, I felt as if I was walking into a real one and wondered if the exhibition by painter Helen McNicoll would set off other echoes. 

An early Canadian Impressionist, stubborn and unwell

McNicoll was born in Toronto in 1879, during Ma Mandelbaum’s New York heyday. She was about to turn four when Mrs. Mandelbaum arrived in Ontario in December, 1884, a delicate child who had already lost much of her hearing to a childhood illness. 

Yet McNicoll was determined, and starting in 1902 she studied painting at London’s fabled Slade School of Art for two years. She lived most of the rest of her short life in England before dying of diabetes in 1915, aged only 35. Until a recent revival, her work had fallen into relative obscurity, just as Mrs. Mandelbaum had disappeared from public notice after her death. 

I found McNicoll’s paintings both beautiful and moving. They’re non-sexualized, subtly-coloured portrayals of women at work: women cooking, tending children and picking apples (but not pockets). The female gaze, I thought. 

In the notes beside her work, there was also a hint of a life partnership with another woman. I wondered if her wealthy and conservative family had kept her work out of the public eye for several decades to try to tamp down questions about her private life.

Maybe McNicoll was another female outlaw.

Maybe women in earlier historical periods were always outlawed if they did more than cook, tend children and pick apples.

The way things are going, maybe we will be again.

I was mulling over all these ideas when a video in one of the exhibition rooms made me stop, sit down and think about Fredericka Mandelbaum from a final angle.

The Bean Field and the BBC

A McNicoll painting called The Bean Field hung on one wall of the small room. On another, the gallery played an episode of the BBC TV series Fake or Fortune, hosted by Fiona Bruce and art historian Philip Mould. Sheila had seen the show before but I hadn’t, each episode featuring the real-life solution to an art mystery. In this case, British artist and dealer named David Taylor had bought a canvas attributed to Helen McNicoll at a local auction in the U.K. for £2,000. If the show could prove it was genuine, he could sell it for as much as £300,000.

Mould and Bruce did their sleuthing by visiting conservators, art historians and highly-trained technicians (largely female) while discussing the sales price with a billionaire McNicholl collector from Quebec (male). Spoiler alert: the canvas proves to be genuine, and Taylor disappears off-camera with collector Pierre Lassonde to discuss the sale.

Before he does, Taylor says something in a bashful voice I that found quite moving. “I’m hoping it might make enough to get a bungalow or something.” The stairs to his flat being a problem because of his knees. 

And here’s where my feelings about Mrs. Mandelbaum took a dive. I thought again about modern business leaders doing what she had done, funding politicians in return for favours. These days it’s legal, but I still find it distasteful that they can buy even greater privilege, ensuring that modern Tammany-style Republicans will approve enormous tax breaks for the rich while cutting programs for poor and middle-class people. 

I told myself to stop romanticizing the con. Criminals usually pick the pockets of people who can’t afford it. 

Margalit Fox points out that Mrs. Mandelbaum’s career was largely non-violent. Only one bank guard was killed by her henchmen over the course of her long career (although I imagine his family missed him). Yet she also helped make 19^th century New York into a kleptocracy of the kind American citizens are facing once again, with effects that reverberate north of the border and around the world. 

Deep down in the rabbit hole, my romanticization of criminals died. Going onto my phone, I found that Jesse James was a Confederate so-called “bushwhacker,” a guerrilla who was involved in a massacre of more than 100 Union soldiers. Bonnie and Clyde murdered at least 13 people. Wild Bill Hickock killed six or seven, usually over petty sums of money. 

The Talented Mrs. Mandelbaum ends up being a cautionary tale. Not only did Fredericka Mandelbaum lose her business, she died in a city she loathed (and that Sheila very much likes, by the way). The great criminal mastermind ended her days lonely, diminished, in pain and in exile.

Yet Fox has written an excellent book, and discovered a remarkable amount about someone who worked to hide both her activities and her feelings. In the end, I was left with only one question. Is it about Ma Mandelbaum’s time or ours? 

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The Talented Mrs. Mandelbaum: The Rise and Fall of an American Organized-Crime Boss by Margalit Fox was published by Random House. It’s available here.

My friend Sheila Murray’s wonderful novel, Finding Edward, won the City of Hamilton book award, among other honours. It was published by Cormorant Books and is available here.