My favorite, because of that grin. Ruby Taylor, arrested in 1942 in connection with an investigation in connection with prostitution.
 
The romantic idea of American prohibition hinges on the myth of an accessible, safe speakeasy for every soul in need of a booze-enhanced nightlife. In actuality, raids on speakeasies were incredibly common, and although owners often bribed police and city officials, actually finding and patronizing a speakeasy could be a real risk for your average Joe. Lesser known were the vacation drinkers, who would migrate up to Montreal on holiday, as it quickly became known as a friendly city of vice for rambunctious Americans. But Montreal had more than an opportunistic liquor economy to boast of.

Montreal looked and sounded like Europe, from the architecture to the French language and culture, giving one’s debauchery the feel of an exotic vacation. Of course, the bedfellows of alcohol (gambling, organized crime, radical politics, and prostitution) also flourished, in spite of a burgeoning movement to purge the city of sin. While moralistic committees for social reform began to organize in 1918, it was only a year later that prohibition went into effect in the US, completely steamrolling (and subsequently exacerbating), the growing anti-vice sentiment.

By the time alcohol became legal again in the States, Montreal was already a sort of Euro-Reno, famous for its brothels. With a sudden rise in venereal disease, the public sentiment on working girls became particularly hostile, and perception of prostitution went from pitying to vitriolic: no longer were they considered poor girls down on their luck, but pathological hussies, tearing apart the very moral fiber of fair Montreal!

Eventually a a full-scale investigation was launched to weed out the corruption and sever the mob ties and various illegal economies. (By 1953, the Commission of Investigation On Public Morality had thrown many a cop in prison, and Montreal was starting to clean up.) Regardless, the laws regarding prostitution were pretty forgiving. Of course, there were still arrests, the records of which are fascinating.

The photos below are of madams, prostitutes, and brothel managers arrested in attempts at a crackdown. It’s amazing how French the fashions appear to be, from darkly-colored geometric cupid’s bows to the snug sweaters and Edith Piaf eyebrows. Many of them are listed as “arrested in connection with an investigation in connection with prostitution,” which would seem to suggest either a large brothel bust, or the cops hassling an individual prostitute to get information for a larger case. If there’s any emotional theme to these headshots, it’s how unimpressed all the women seem to be with the authority that’s arresting them.
 

Anna Labelle, aka Mme Émile Beauchamp, the most powerful madam in Montreal during the WWII. She would drive to the courthouse in a Cadillac wearing a mink coat. Her clients were often from the same police force that busted her.
 

Annie Parker, arrested in 1941 in connection with an investigation in connection with prostitution.
 

FleuretteDubois, arrested in 1942 for keeping a brothel.
 

Irène Lavallée, arrested in 1940 in connection with an investigation in connection with prostitution.
 

Liliane Brown, aka Ida Katz, arrested either in 1930 or 1940, high level madam.
 

Mary Shepperd, arrested in 1940 as part of an investigation in connection with prostitution.
 
Via Archives de la Ville de Montréal