Until the arrival of New York’s Cosa Nostra in Montreal in the early 1950s, gambling and underworld crime were locally-run, and from the 1920s until the 50s, many Jews were actively involved in these illicit enterprises.
Max Shapiro came to Montreal from Poland in the 1920s and ran one of the most successful gambling houses in the city. Eventually, with partners, he opened the famous Ruby Foo’s hotel and restaurant.
Harry Feldman, of New York, owned a three-storey building on Bleury and Ste-Catherine, where the ground floor housed a legitimate business, but the upper floors were dedicated to bookmaking. Unlike his contemporaries, he lived quietly and did not get involved in the drug trade. He was a part owner of many significant establishments, including Chez Parée, and was known as a good family man. In fact, over the course of his 14-year career, he was never apprehended and his organizational skills were even praised by the chief of Montreal police at the time, Pacifique Plante.
Harry Davis of Romania was another prominent local gambler, responsible for the first underworld killing in Montreal. In 1935, he had Charles Feigenbaum—a police informant whose testimony had resulted in Davis’ 14-year sentence for smuggling morphine—murdered on Esplanade across from Fletcher’s Field. After several years in jail, Davis returned to the city in the mid-1940s and regained his title as gambling Tsar, controlling who could open gambling venues in the Red Light District and taking 20% from each. His rule came to an end on July 25, 1946, when he was shot to death in his gambling house at 1244 Stanley Street. He was killed by Louis Bercowitz, who did not receive Davis’s permission to open his own gambling establishment. Davis’s death permitted Harry Ship to dominate the gambling trade until his mistakes brought the New York Cosa Nostra to Montreal, engendering a new era of organized crime.
Harry Ship, called the King of the Montreal Gamblers, was a major bookmaker and operator of illegal casinos all over Montreal. Born in 1915, Ship studied mathematics at Queen’s University. Although he did not graduate, he excelled in his studies and was highly respected among his peers. He returned to Montreal in 1940, where he established a series of “white houses” along Ste-Catherine Street. Each house contained five telephone lines, blackboards and operators’ headsets, so bookies could take bets and write them up simultaneously. Business was so brisk that the apartments were often subdivided into halves and quarters to be able to house all the bookmakers. He also operated illegal casinos in Lachine, Greenfield Park, and on a farm in Côte St. Luc. Ship admitted that he made $1M annually, from 1940 to 1946 (equivalent: $15M today).
Although he lived lavishly, including owning a mansion in Outremont and the Chez Parée nightclub, which featured acts such as Frank Sinatra and Dean Martin, his operations were frequently raided and he paid huge sums of money to the local police. Eventually, he was arrested and sentenced to six months in jail.
Perhaps Ship’s legacy to Montreal is the introduction of New York’s Cosa Nostra into the city. It seems that Ship owed money to Frank Erikson, the wealthiest bookie on the East Coast, whose silent partners included Meyer Lansky, Frank Costello and Lucky Luciano. Due to his indebtedness, Ship was forced to accept the interference of the New York families in the early 1950s, which resulted in the Montreal underworld being controlled from New York, and the city becoming an important center for bookmaking and heroin smuggling. Little is known about Ship after this period, except that his is buried in the only family circle at the Baron De Hirsch Cemetery in Montreal and he, like so many other iconic figures, is immortalized in Mordecai Richler’s novel, The Apprenticeship of Duddy Kravitz.
Schneider, Stephen. Iced: The Story of Organized Crime in Canada
D’Arcy O’Connor, Montreal’s Irish Mafia: The True Story of the Infamous West End Gang
Stephen Schneider, Iced: The Story of Organized Crime in Canada
Kristian Gravenor, http://coolopolis.blogspot.ca/2011/10/montreals-top-10-gangland-murders-10.html