She and her common-law husband, Italian-born Rocco Perri, established a business in bootlegging after the sale and distribution of alcohol was prohibited in both Canada and the United States.

[2] Starkman immigrated to Canada circa 1900, settled in The Ward, Toronto, Ontario with her parents, and married Harry Tobin by the age of 18.

[2] Starkman found life as a housewife within a traditional Orthodox Jewish household to be unbearable and she longed to escape from her marriage.

[10][8] When the Canadian government cut funding to the Welland Canal project due to World War I, Perri became unemployed.

However, Perri and Starkman found a better means of income when the Ontario Temperance Act came into effect on September 16, 1916, as it restricted the sale and distribution of alcohol.

[13][14] Perri and Starkman also opened brothels in Hamilton, at the time the city with the highest percentage of its women engaged in prostitution in North America.

Despondent, Routledge committed suicide by jumping from her lawyer's seventh-story office window of the Bank of Hamilton; her parents took custody of their children.

[23][20] Perri and Starkman survived financially in the few years after 1915 from his income as a macaroni salesman and their grocery store on Hess Street.

After the Ontario Temperance Act was passed in 1916,[24] making the sale of alcohol illegal, the couple started selling shots of Canadian whisky on the side.

[31] The couple were also reported to have taken part in drug trafficking as early as 1922, when the Royal Canadian Mounted Police (RCMP) suspected Perri of "dealing in narcotics on a large scale.

[33] Whatley, who had been born in rural Somerset in 1878 was a veteran of the Boer War who had settled in Canada in 1907 and joined the Hamilton police force in 1910.

[33] A colourful, striking figure who dressed flamboyantly and ran the Hamilton police force in a militaristic style, Whatley was very fond of gambling on horses, and he was so close to Starkman that the tabloids accused them of having an affair.

[34] Starkman realized that to win market share in both Canada and the United States required the gang to sell high-quality and safe alcohol.

[35] Hatch stated about his business relationship with the Perri-Starkman gang: "The Volstead Act doesn't stop us from exporting our whisky south of the border; it does, however, prohibit Americans from importing it.

[37] As such, illness and death from drinking tainted alcohol were major problems in the 1920s in the United States and in the "dry" areas of Canada.

[37] The Gooderham & Worts alcohol brewed in Montreal, ostensibly only for sale in Quebec, by contrast was known to be safe to drink and the exclusive contract that Starkman negotiated with Hatch proved to be a major factor in the rise of the Perri-Starkman gang.

[40] 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.

[39] Starkman was known for dressing in a modernist "flapper" style with her hair cut short while wearing expensive clothing and jewelry.

[39] She was a great fan of the music of Louis Armstrong, Duke Ellington, Bessie Smith and Scott Joplin and avidly collected the records of their songs.

[31] In 1927, Perri was compelled to testify at the Royal Commission on Customs and Excise inquiry, focusing on bootlegging and smuggling, and also at a hearing on tax evasion charges against Gooderham and Worts.

[44] In 1929, an undercover officer of the Royal Canadian Mounted Police (RCMP), Frank Zaneth, infiltrated the Perri-Starkman gang.

[48] Italiano was offered a plea bargain by the Crown under which his sentence would be reduced in exchange for testifying against Starkman and Perri, but he literally observed Omertà by saying nothing in response.

[52] Perri wanted Starkman's funeral to be a lavish affair and he purchased a $3,000 coffin for her that was a copy of the one that was used to bury the actor Rudolph Valentino in 1926.

[54] In Canada, Starkman's funeral upstaged the media coverage of the first British Empire games, which were being held in Hamilton at the time.

[54] Starkman's former husband, Harry Tobin, told a reporter from the Daily Toronto Star: "Seventeen years ago she left me with two small children.

[56] Inspector John Miller of the Ontario Provincial Police, who was assigned to investigate the murder commented that Starkman had many enemies as he noted that the Italiano, Silvestro, D'Agostino and Papalia families all hated her.