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Like any large North American city with a long history, Montreal has its share of gangsters, gamblers, mobsters, and mafiosi fighting for control of the city’s illegal activities. As a major port, Montreal has been more popular than most, and it has been a fought-over locale for organized crime syndicates over the years. Of course, when the mob moves in, murder inevitably follows. To describe every ghastly homicide committed by mafia members over the years would be an impossible and stomach-turning task. But here, in no particular order, are just a few noteworthy murders carried out by the mob.

Harry Davis, Jewish Mob Boss, 1946

During the ’30s and ’40s, when gambling was illegal in Canada, the underground gambling operations in Montreal were mainly run by the Jewish mafia. In 1946 Harry Davis was the “edge man,” the boss of the Jewish mafia. He was also involved in drug smuggling, for which he had served twelve years in prison at Montreal’s St-Vincent-de-Paul Penitentiary. His former partner, Charles “Charlie” Feigenbaum, testified against him, and it’s believed that Davis ordered Feigenbaum’s murder. That hit was one of the first gambling-related homicides to occur in the city, but it was certainly not the last.

When Davis was released from prison in 1945, there was no new boss in power, and he quickly moved in to fill the empty spot. Reopening his gambling parlour at 1224 Stanley Street, Davis took control of all gambling in Montreal, forcing anyone who wanted to get in on the game to go through him first.

One such person was Louis Berkowitz, who wanted to open an illegal bookmaking business. Believing there were already too many of them in operation, Davis denied his request and burned down his place on Mansfield Street for good measure. Things escalated quickly after that. After hearing that Berkowitz was coming after him, Davis put out a hit on him. But not soon enough. On July 25, 1946, Berkowitz met up with Davis and shot him to death in his gambling parlour. Shortly thereafter he confessed to the murder to the editor of the Montreal Herald, Ted McCormick, hoping this would somehow get him a shorter sentence. He would eventually serve twelve years.

After Davis’s death, the Montreal underworld was in chaos. The public was outraged to learn that organized crime had such a tight hold on their city, and the police began to crack down in earnest. This led to a brief slowdown in the city’s illegal operations, though hardly an end.

James MacDonald, West End Gang Hitman, 1969

You wouldn’t be able to guess that Andrew’s Pub on Guy Street was once the site of a vicious gangster killing, but it was. It was 1969 and the place had a different name — The Cat’s Den Lounge — and it just happened to be the headquarters of the West End Gang, Montreal’s Irish mafia.

On March 15, just two days before St. Patrick’s Day, the place was packed when two men came in from the fire escape. One held a revolver, and the other an M-1 machine gun. They wasted no time approaching James MacDonald, a large man known to be an enforcer for the West End Gang. Perhaps the trio exchanged words, or perhaps they didn’t. All we know for sure is that moments later the M-1 was unleashed and MacDonald was hit seventeen times, his torso ripped to pieces and his brains spewed across the bar.

The killers (some believe they were themselves members of the West End Gang who suspected MacDonald was about to turn informant) then fled the scene, tossing the machine gun in the parking lot. In the end, no arrests were ever made, because no one in the bar would admit to having seen a thing.

If you visit Andrew’s Pub today, it’s unlikely you’ll witness a mafia gun battle, but you might just get a whiff of blood and gunpowder in the air. It’s said that every few years a patron reports smelling these scents. Some say they feel as though they’ve been bumped into from behind by a large person, but when they turn around there’s no one there. Others have claimed that glancing in one of the bar’s mirrors, they’ve seen a man stumbling around behind them, headless and reaching out to grab them. But again, when they turned around, there was no such person to be seen. This can’t be James MacDonald, lingering at the bar for just the right moment to enact his final revenge. Or can it?

The Brossard Massacre: The Dubois Brothers, 1975

In 1975, the worst crime ever seen on the South Shore of Montreal was committed by the Dubois brothers. This gang, led by nine brothers of the French-Canadian Dubois family, was known for its involvement in prostitution, drugs, and loansharking. It was once referred to as the most influential criminal group on the island, and at its height was feared by both the motorcycle gangs and the mafia.

The conflict that would lead to the murders in Brossard began when the McSweens gang, who had previously worked with the Dubois brothers, tried to branch out on their own. In the violence that followed gang boss Jacques McSween was shot and killed, and two members of the Dubois gang were murdered in retaliation. The Dubois brothers were out for blood, and it all came to a head on February 13, the night before Valentine’s Day.

Three masked Dubois gang members entered the bar in Hotel Lapiniere just a few minutes before midnight. It was country music night, and there were about fifty people inside. Interestingly, they came in just as there was a pause in the music, and a mime had taken the stage to entertain the crowd. As a part of his act, the mime was shooting off a fake gun when the real shooting started, causing some in the crowd to believe the noise was just a part of the act. But the bullets the gangsters sprayed into the crowd were very real.

In the end, four men were killed, including the doorman, a cab driver, and a waiter. Roger Letourneau, one of the targets and the then leader of the McSweens, was shot twelve times and killed. The shooters got away but later Pierre McSween would claim that Roger Fontaine had been among them. Fontaine was found dead in his camper a year later. He had been shot in the head and the camper set on fire.

The Lennoxville Massacre: The Hells Angels, 1985

In the early ’80s the Montreal Hells Angels was divided into two chapters: the Montreal North chapter based in Laval, and the Montreal South chapter, which was oddly not based in Montreal, but in Sorel, Quebec. The Laval chapter was known for being wild and unruly, often using the drugs they were supposed to sell, and behaving like typical bikers. The Sorel chapter, by contrast, was better disciplined and more inclined to act like elite drug dealers and businessmen. They decided that something had to be done about the Laval chapter, before their aggression and run-ins with the law did real damage to the Hells Angels in Quebec.

In a secret meeting held in Sorel in 1985, the leaders of the Halifax, Sherbrooke, and South Montreal chapters came to the decision that the Montreal North chapter needed to be purged. A party was planned for March 23 at the Sherbrooke chapter’s Lennoxville clubhouse as a ruse to get the North chapter all in one place for the brutal bloodbath.

Five Montreal North chapter members, including its leader, were ambushed that day. They were surrounded by forty-one men and shot to death in the clubhouse. Two other members were forced to retire, and two more were told join the Sorel chapter or die. The Laval clubhouse was looted and the five bodies were wrapped in sleeping bags, weighted down with metal plates, and dumped into the St. Lawrence River.

The Lennoxville Massacre was considered extreme and vicious, even by criminal standards, as these Hells Angels members had slaughtered their own. Dissatisfaction with these actions led to the creation of the rival biker gang the Rock Machine in 1986. The Quebec Hells Angels and the Rock Machine would later take part in the Quebec Biker War, a violent turf war that would last eight years.

The Italian Mafia Murders

Since the 1950s, the Sicilian mafia has been the dominant criminal organization in the city, with their leaders ruling Montreal’s underworld. One of the most notorious of these was Nicolo Rizzuto. To describe even a small portion of the hits the Rizzuto clan has been involved in during the past sixty-odd years would be impossible, but here are the bullet point (pun intended) murder “highlights,” presented to you in chronological order.

Pietro Sciarra, Paolo Violi’s consigliere: Shot dead as he left the Riviera theatre where he’d seen The Godfather (1976). Sciarra was a snitch who betrayed the Rizzuto family. His death was the first in a series of murders to hit the Violi clan.

Francesco Violi, a brother of Paolo Violi: Gunned down in the office of Violi Importing and Distributing while his brother was in jail (1977). Francesco had taken over leadership of the Violis while his brother was in prison.

Paolo Violi, the head of the Cotroni faction of the Montreal mob: Shot in the head while playing cards at a café two months after getting out of jail (1978). Violi’s killers, all Rizzuto associates, were given short sentences for the killing. Paolo Violi’s death ended the reign of the Violis in Montreal, and allowed that of the Rizzutos to begin.

Rocco Violi, another brother of Paolo Violi: Shot in his kitchen by a sniper (1980). Rocco was the last of the Violi brothers. His death has often been deemed unnecessary, as he was not an important figure in the Violi clan.

Nicolo Rizzuto Jr., a grandson of the Rizzuto patriarch: Gunned down on a residential street in the Notre-Dame-de-Grâce neighbourhood in broad daylight at the age of forty (2009). He was allegedly killed by Haitian street gang leader Ducarme (Kenny) Joseph, who himself was shot and killed in 2014. Rizzuto Jr.’s death was seen as a definite challenge to Rizzuto rule, and sparked a mob war that went on for five years.

Agostino Cuntrera, acting boss of the Rizzuto clan while Vito Rizzuto was in prison: Shot outside a whole food warehouse in Saint-Léonard, aged sixty-six (2010). Cuntrera was one of the gangsters implicated in Paolo Violi’s murder years before.

Nicolo Rizzuto, patriarch of the Rizzuto crime family: Killed in his Cartierville mansion by a sniper at the age of eighty-six (2010). Rizzuto’s killing was the most high-profile of the mob war. His alleged killer, hitman Salvatore “Sam” Calautti, was killed in 2013.

Salvatore Montagna, the boss of the New York Bonanno crime family, which was attempting to take over the Montreal Mafia: Shot and then drowned in the Assomption River (2011). Montagna was believed to have been involved in the recent Rizzuto killings. A Rizzuto associate was charged with his murder.

Lorenzo Giordano, a high-ranking member of the Rizzuto clan: Shot in his parked car in Laval, three months after being released from prison (2016).

Rocco Sollecito, a high-ranking member of the Rizzuto clan: Shot driving his BMW SUV in broad daylight (2016). Sollecito and Giordano were two of six men vying for leadership of the disordered Montreal mafia.

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Organized crime is alive and well in Montreal. Though a 2009 police crackdown on drug trafficking, which resulted in over 150 arrests, had the Hells Angels laying low for a time, a number of recent raids on member homes and clubhouses have proven that their illegal activities continue. The Rizzutos may not be as strong as they once were, but two of their leaders, Leonardo Rizzuto and Stefano Sollecito, were recently brought up on charges of gangsterism (they were eventually acquitted and released). The West End Gang lives on. Average Montrealers may remain largely oblivious, but organized crime continues to operate all around them, and hits are still being carried out all the time. So, keep your eyes and ears open, citizens. You never know who might be next on the mob’s never-ending hit list.