Being the first woman to do the job doesn't mean they'll like you.

Normally, one starts a story at the beginning, but this is best understood by its ending. In 1930, Frederick Griffen wrote about a funeral in Hamilton Ontario that may still hold the record for the largest, most flamboyant funeral the city has ever seen with over 20,000 attendees.

The article seems, at first glance, full of over the top descriptions but, history has confirmed the accuracy of the details.

"She had lain in state, like a princess, for three days and nights while ten thousand people filed in to see her… The massive coffin of bronze, with heavy silver steel trimmings, was scarcely to be seen, hidden, as it virtually was, with flowers. What flowers! I am not an expert in funerals but, personally, I never saw anything to equal them."

Her two daughters "had to be borne aside in a semi-comatose state of bewilderment and woe." and from the cellar below, her German Shepherd bayed loudly.

"At the head of the coffin was a magnificent pillow of mixed flowers, orchids, roses, gladioli and other blooms, literally hundreds of them, [with] a wide ribbon of gauze. And on it in letters of gold were the words, “To my wife.”

The man who organized and paid for the funeral, Rocco Perri, sat, overcome with grief between her daughters but he was not the father of her daughters nor, despite the gold inscription he wrote on the ribbon, was the woman his wife and, although the funeral he organized and paid for was a Jewish funeral, Rocco was not Jewish but, rather, an Italian immigrant.

The woman he was burying was Bessie Starkman, the first female Canadian organized crime boss. She was gunned down, at the age of forty, in the garage of the home she shared with Rocco, who was referred to as "Canada's Al Capone" and was one of the most prominent Prohibition-era crime figures in Canada.

Bessie Starkman was born into a Polish Jewish family, immigrated to Canada at about the age of ten. At age eighteen, she married Harry Tobsen, a driver at a bakery, and had two daughters. In 1912, they took in a boarder named Rocco Perri. After a brief romance, Starkman left her husband, children and Jewish faith for Perri. They lived in St. Catharines, Ontario, where Perri had a labourer job, and then moved to Hamilton. Perri worked as a travelling salesman until the couple opened a small grocery store.

They went from ordinary, low paying jobs to becoming mob bosses with a lavish lifestyle, including diamonds and expensive cars, because of the Ontario Temperance Act of 1916; boot legging became a new money maker. Perri became the 'King of the Bootleggers' and, ignoring the rule that women can't join the mob, he made Starkman the first female crime boss. She negotiated orders of liquor and beer, laundered money and dealt with other gangs. They operated in Kitchener, Toronto, Windsor, Hamilton and Niagara, ran bootleg liquor to Detroit, Chicago and New York State and were involved in prostitution. When prohibition ended in 1927, the couple then moved on to illegal drugs and gambling.

The Italian-Canadian journalist Antonio Nicaso wrote: "Up to that time, a woman's role in the underworld was relegated to wife and mother, or mistress and prostitute. Until Bessie came along, none had been in a position of authority in a major crime gang-let alone entrusted to manage a massive flow of dirty money."

Of course, being a mob boss, even the first woman mob boss, meant that Bessie was involved in violent interactions with people. Her relationship with Rocco was also troubled and she left him and returned a number of times. Despite his progressive views of women in the mob, Rocco had an old fashioned wandering eye. He had an affair with Sarah Routledge, beginning in 1918, and had two daughters with her. He maintained a home and paid child support. Sarah, when falsely informed Rocco was married to Starkman, committed suicide in 1922.

Bessie's murder was never solved but much was written about it:

"Bessie died after being ambushed by two men with shotguns in the garage of their home, Aug. 13, 1930. She had alienated so many people, including possibly her own husband, police could not narrow the list of potential suspects to a workable number."

Though the 'alienated' husband was not married to her, he threw a heck of a funeral for her. Or was it her actual husband, who she never divorced, who killed her?

The first woman to do any job often garners respect and admiration. Not so with Bessie Starkman. The qualities that made her successful were the same as any mob boss: she was ruthless, greedy and had emotionally volatile relationships. The 20,000 people at her funeral were not devoted friends but were mostly strangers drawn to the spectacle of a very expensive funeral. The title of the article by Frederick Griffen says it all:

Grotesque Ceremony Becomes Free-For-All of Morbid Curiosity

Twenty Thousand Mill and Fight to See Bessie Perri’s Magnificent Funeral