Harry Ship: how his bad luck gambling streak put Montreal into the hands of the New York Mafia

Ship and wife Ida

 How did New York's Italian Mafia obtain its grip on Montreal's underworld? 

   Blame Harry Ship's gambling addiction. 

  Ship (born Shipshovitz) was a Jewish hustler who was great with numbers, as was his entire family. His gambling business associate brother Louis, who stood a tiny 4'6," would routinely outduel mechanical calculators whenever challenged. 

   Ship started in industrial-scale gambling and bookmaking in 1940, installing multiple phone lines in various apartments around town. 

   Ship used all the newest technology available, telegram services, sports tickers and a projector with the latest race results. Bell Telephone demanded a $1,000 monthly deposit just to operate his phone service, as his long distance bills were so costly.  

   Harry and his circle - which included David Miller, father of Future Electronics billionaire Robert Miller - were effectively math gangsters. They offered an "edge man," service which insured other gambling houses payoffs on longshot bets. The gambling insurance premium calculations had to be done instantly over the phone.   

Ship at a 1948 gambling hearing

   Ship later claimed that his gambling enterprise earned him $1 million a year between 1940 and 1946, a period which saw police raid Ship's operations 34 times. 

   Police would frequently padlock Ship's operations, using a municipal bylaw that was later imitated by provincial legislation that allowed police to lock out suspected Communist organizations in Quebec. Ship paid a ton in bribing Montreal police but always denied doing so under oath. 

   Ship was also a big gambler himself and eventually became indebted to mob-connected American bookies. According to his son Neil Sheppard, 

   My dad would bet at least $100,000 every day on games. He'd take a sport: horse racing, basketball baseball, whatever and he'd choose 10 teams or 10 horses, 10 pitchers etc, and he'd bet $10,000 on each race or game. So at  $100,000 per day, a few straight bad months could be quite a few million.

  Ship's debt was owned by Frank Erikson, a big American bookie close to New York mob kingpins Meyer Lansky, Lucky Luciano, Frank Costello and others.

  Top Montreal mobsters of the time, the duo of Luigi Greco and Frank Pretula - both previously bodyguards of the slain Jewish Montreal crimelord Harry Davis - set up a deal with Ship to allow Costello and Luciano into his operations. 

   Greco and Pretula remained friendly with Ship. Pretula - who would eventually disappear and be presumed dead - would often visit the Ship home. 

Frank was a charmer. He visited a lot over the period of a few years. I was six or seven, so it must have been 1952-1953. I somehow got to calling him Uncle Frank. He was a very handsome and confident guy, a sharp dresser as I recall and he always spent time with me when he came over, something my dad had no time for. So it was easy for me to look up to him.

One day he showed up with a little puppy that he gave me. I was begging for one and he heard me. I never forgot that. Naturally I always anticipated his next appearance with excitement. At some point after he hadn't been around for a longer than normal interval I started to ask. When's uncle Frank coming? How come he doesn't come by?.

My mom sat me down one day and told me he had to go away and probably would be unable to return. It really made me sad.

   Ship's relationships with the New York mob led a flood of New York mobsters to moved to Montreal or visit frequently, including Carmine Galante. Canadian authorities deported Galante back to the States in 1954. He left Greco and Cotroni in charge of his local operations.

  Harry Ship was standing in the kitchen of the Sahara Club, a basement belly-dancing basement club on Sherbrooke near Bleury that he had ownership stake in, after midnight on Tuesday 17 July 1962. A gunman, hiding his face with his jacket, approached Ship and shot him twice in the legs. Ship was rushed to hospital and recovered from his wounds.

   One version credited the shooting to Carmine Galante as a message for Ship to stay in line. Ship believed that the shooting was a spontaneous act by an independent criminal disgruntled about some other petty issue. 

  Ship and Galante remained "very close" according to his son Neil.

   Ship had a moral dilemma, as he virulently opposed the use of illicit drugs but he was also in business with Galante, who was a massive trafficker and brought drugs into Canada and who purportedly even sometimes held drug addicts prisoner to test drugs on them. 

  Ship was likely complicit in the importation of heroin into Canada. 

    I don't think that Luciano and Galante would be talking to my dad about girls or gambling. It seems the distribution routes were set up over when they were all in town meeting with my dad. 

  There was also a lot of speculation that my dad was coerced into helping on that because at one time he was into them for a large sum of money after an unlucky betting streak that lasted for months.

  Ship's guilt of being involved with heroin importers was further compounded when his own son Neil developed a debilitating heroin addiction that he eventually kicked. 

  Ship's three other kids included a daughter, who briefly married Montreal Irish Mafia kingpin Johnny McGuire, which was seen as a sort of underworld royal wedding.  She also married another man who, shockingly, shot himself dead in front of her during an argument. The husband's parents offered to compensate her for the trauma but Harry insisted she refuse any such payment.  

  On 11 July 1979, Ship took his family to dine with Galante one day before he was murdered in a restaurant. According to Neil, Harry Ship could easily have died alongside Carmine Galante. 

   We were all at dinner in New York with Carmine Galante, who smoked one of the Havana cigars we brought him that night. He asked my dad as we left, "Hey Harry, do you want to meet me for lunch tomorrow. I'm going to this little place called Joe and Mary's?"

 "Maybe I will Carmine, I'll let you know."

   The day after I saw the news, I worried that my dad was one of the people under the sheets who they didn't unveil. It wasn't until real late that day he called to say he left town and he and my mom were back in Montreal.    

    Harry spent his later years facing financial challenges but managed to unexpectedly make a small fortune on real estate in the Laurentians later in life. He suffered a stroke that left him incapacitated in his last years on earth. Harry Ship (1915-1998) outlived his brothers and sisters Bella, Sarah, Alec and Louis.

 Ship is now best-remembered as the frequently-referenced Boy Wonder character in Mordecai Richler's novel/movie The Apprenticeship of Duddy Kravitz. Richler's fictional Ship character was involved in heroin importation but Richler confessed that he based the story on gossip and didn't actually know whether Ship was complicit in heroin schemes.

   City Unique, William Weintraub's authoritative account of Montreal in the 1940s and 1950s, is also believed to have been heavily-influenced by Harry Ship's accounts. 

   Harry Ship remained married to Ida Lebovitch for his entire life and left children Barbara, Neil, Gary and Michael. Ship's cousin, a noted local architect, also bore the
name Harry Ship.