During our Sins of the City Vancouver walking tours, you’ll learn about Vancouver’s legendary crusaders, criminals and characters. Uncover the true origins behind “Gassy” Jack Deighton’s moniker, or learn about the nefarious activities of famed gangster, Joe Celona. The mysterious men and women from Vancouver’s past will thrill, shock and take you on a whirlwind ride of sin.


“Gassy” Jack Deighton (November 1830 – May 23, 1875)

Many incorrectly assume Gassy Jack’s nickname stems from the fact that he was a gassy man. Our Vice, Dice and Opium Pipes Vancouver walking tour reveals the real reason for his title and delves deep into his influence on Gastown and Vancouver’s development during a time of lawlessness and debauchery. For example, Gassy Jack established Vancouver’s recreational alcohol culture with nothing more than bravura, barrels of whiskey and tenacity. He also started Vancouver’s first independent business: a saloon on the shores of the Burrard Inlet.  Learn more about him in our Vice, Dice and Opium Pipes historic walking tours.






Joe Celona (March 7, 1897 – March 4, 1958)

Long hailed as Vancouver’s version of Al Capone, Joe Celona was charismatic crime lord who hailed from Italy and who had his hand in everything from bootlegging to bawdy houses. With nicknames such as: “Public Enemy #1,” and “Mayor of East Hastings,” Celona’s tight ties with city authorities led him to become the undisputed ruler of Vancouver’s underworld. Find out how he evaded and controlled the authorities, built an empire of vice and, eventually, had it all come tumbling down in a flurry of drama in our Vice, Dice and Opium Pipes Vancouver walking tours.






L.D. Taylor (1857 – 1946)

While he looked gentle and quiet with his owlish glasses, Louis Denison Taylor was known as one of Vancouver’s most colourful and controversial political figures. Between 1910 and 1934 Taylor was elected as mayor eight times, winning him the title of longest-running mayor in Vancouver history. You could say that he appealed to a “diverse” demographic, as his protocols often catered to the needs of both working-class families and notorious criminals. Taylor’s lenient approach to condemning debauchery, and close ties with local gangsters, made it clear that Vancouver was no Sunday school town. Learn more about L.D. Taylor in our Vice, Dice and Opium Pipes walking tour.






A house much like the one Birdie Stuart would have occupied.

Birdie Stuart (dates unknown)

The beginning of Vancouver’s sex trade can be traced all the way back to 1871, the year that San Franciscan Birdie Stewart came to town. Starting her trade over a decade before Vancouver’s incorporation, Birdie ran the city’s first disorderly house out of a quaint white cottage with a painted white porch. With Vancouver’s predominantly male population, Birdie’s brothel was a guaranteed success, and it was not long before dozens more entrepreneurial women crossed the Canadian border to join her. Learn more about the history of Birdie Stewart in our Red Light Rendezvous walking tour.





Frankie E. Russell (dates unknown)

Frankie E. Russell was one of the most notorious sex workers in Vancouver history…but not for reasons you would typically imagine. Between 1910 and 1916, Frankie faced numerous arrests for everything from vagrancy and drug possession, to stealing diamond rings and committing murder. She was far from the dainty type, and demanded respect from her customers, stating that “if the ‘Dicks’ were not careful they would ‘get it!’ Learn more about the history of Birdie Stewart in our Red Light Rendezvous walking tour.



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