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Members of Administrative Department of Security (DAS) escort Canadian pilot Jean-Raymond Boulanger, centre, in Bogota in March, 2000.HO/Agence France-Presse

Even after a spectacular failure, Raymond Boulanger couldn’t help but ham it up for the press. It was November of 1992 and the Quebec pilot and some time mercenary flyer for the Central Intelligence Agency had just been caught attempting to import four tonnes of cocaine aboard a Convair 580 aircraft that he landed at an abandoned military airstrip in northern Quebec.

Mr. Boulanger and his three Colombian accomplices were being marched into a courtroom in La Tuque, Que., to face charges of drug trafficking. It was considered the largest-ever drug bust in Canada at the time, estimated by police to have a street value in the billions of dollars. The Colombians tried to hide their faces but Mr. Boulanger, in contrast, turned to the TV cameras, broke into a big smile and winked.

That wink helped transform Mr. Boulanger, who went on to serve close to 20 years in prison, into a Quebec celebrity, who later helped pen his own biography and was the subject of a documentary series on Crave. Charismatic, articulate, charming, Mr. Boulanger, who died of cancer on March 19 at the age of 76, was a talented pilot who lived on the edge for years, hauling cocaine and marijuana for Colombian drug cartels and delivering military equipment to the Contras in Nicaragua as well as to regimes in Libya and Iran, in breach of sanctions.

Nicknamed the “Cowboy,” Mr. Boulanger was above all an adventurer, who managed to escape detention in Canada twice. After the first escape, he ended up back in Colombia, only to be kidnapped by left-wing guerrillas and held until a ransom was paid. Arrested by Colombian police, he was shipped back to Canada and returned to prison.

“Boulanger was unbelievably cool,” said René Pelletier, the RCMP officer who arrested him, said in the documentary film, Le Dernier Vol de Raymond Boulanger (The Last Flight of Raymond Boulanger). “He was like Arsène Lupin, the gentleman trafficker.” Lupin is a fictional French thief.

“I have no regrets. I have no remorse,” Mr. Boulanger said years later, insisting he felt no responsibility for the impact that drugs have on society. “I’m a professional. I did my job.”

“He was a rebel,” said Daniel Renaud, a crime reporter for La Presse and author of Raymond Boulanger, Le Pilote Mercenaire, published in 2013. “I’m not sure he even did it for the money.”

John Raymond Boulanger was born in Rimouski, Que. on Feb. 17, 1948, the second son of Wilfrid Joseph Boulanger, an accountant, and his wife, the former Jean Rennie Crichton, a war bride whom Wilfrid met while serving with the Canadian Army in Scotland during the Second World War.

The family moved to Mont-Joli, where Raymond’s father worked for a foundry. Raymond attended school in English, located near an airfield that was a hub for construction of the DEW Line network of Cold War-era radar stations. It was here that Raymond was bitten with the flying bug. At 16, he landed a job working for Quebecair in Wabush, Labrador, as a weather spotter. This is where he first flew a plane.

Moving back to Montreal, he earned a commercial pilot’s licence and began working at a private flight school as an instructor. In 1967, he accompanied a friend on a brief flight north of Montreal on a single-engine light aircraft. It crashed and Mr. Boulanger’s friend was killed. Mr. Boulanger was injured but survived.

A few years later, Mr. Boulanger was working as a bush pilot out of Dolbeau, Que., when he was sent to rescue five Americans from a fishing camp as a forest fire raged around them. He completed the task but en route back to base, he was blinded by the smoke and forced to land the plane on a nearby lake, where he and the tourists spent 13 days on an island before being picked up by the Canadian Forces.

Yet Mr. Boulanger was restless. He met Peter Knox, a pilot and Hollywood stunt man, who suggested he get involved in the business of flying DC-3s from Texas to Mexico, returning with loads of marijuana. It was his first drug run. Later, he began flying bales of marijuana from Colombia to a clandestine landing strip in the Florida Keys.

After a failed first marriage, Mr. Boulanger married Jane Thompson, with whom he had two children. He tried to settle down and began working as a pilot spraying Quebec forests against spruce budworm. He bought a hotel in the Gaspé region, which he planned to renovate, but it burned in a fire before the project came to fruition.

Mr. Boulanger then got a job working for Southern Air Transport, a Miami-based airline that was a front for the CIA and did weapons deliveries to anti-Sandinista rebels in Nicaragua. During this period, he also did business with Colombian drug cartels, including the notorious Pablo Escobar, whom he described as being “quite pleasant” but also “ruthless.”

The cartels had run into a problem. When their drug flights were discovered, U.S. authorities would seize the planes and sell them at auction. The cartels were anxious to get them back. So Mr. Boulanger, acting as an aircraft broker, began buying up seized aircraft at sheriff’s sales in Miami and selling them back to the cartel.

In the late 1980s, he and his father were heading to Miami from Montreal and decided to fly out of Burlington, Vt. At the border, their car was searched and border agents discovered US$65,000 in cash in a suitcase, the down payment for a plane Mr. Boulanger planned to buy at auction. He was arrested and spent 14 months in a U.S. prison for transporting undeclared cash across the border.

On release, he got back into the game, this time serving as a middleman for the sale of military aircraft parts to Iran and Libya, which were subject to U.S. sanctions. He would buy the parts in the U.S., import them to Canada and ship them off to Belgium, where they would be trans-shipped to their final destination.

In 1992, Mr. Boulanger got a call. The Montreal Mafia had a deal to import a big shipment of cocaine from Colombia. Mr. Boulanger agreed to organize the flight. On Nov. 19, 1992, he and his crew flew out of a desert airstrip in northern Colombia aboard the Convair, loaded with 4,343 kilos of cocaine, 45 barrels of fuel and a couple of submachine guns.

Soon after takeoff, he realized that he was being tracked by U.S. patrol aircraft, so he veered further out into the Atlantic as he headed north. As he approached the Nova Scotia coast, he managed to elude two CF-18 fighter jets, flew low over New Brunswick and landed in Casey, Que., site of a disused air strip.

There was a problem. Because the flight was late, the accomplices who were due to pick up the drugs had left and Mr. Boulanger and his crew were abandoned. The RCMP tracked them down in Casey and all four men were arrested. They eventually pleaded guilty to drug trafficking. Mr. Boulanger got 23 years.

After five years in a penitentiary, Mr. Boulanger was transferred to a halfway house in Montreal in 1998. He found it too noisy and took off, shaved his mustache and headed to Colombia where he resumed working as a pilot, only to be kidnapped by Marxist guerrillas. He was held for a month before being released. He was arrested by Colombian police and sent back to Canada after being on the lam for 18 months.

After returning to prison, Mr. Boulanger eventually saw another opportunity. In 2001, while on a community work project at a minimum-security prison, he bolted again, fleeing to Mexico. But his father was ill in Montreal so he decided to fly home. During that stay, he went to a Western Union office to make a money transfer and used a fake driver’s licence. He was soon back in jail.

The National Parole Board wasn’t pleased. In a series of subsequent rulings, it refused Mr. Boulanger parole. “You possess pro-criminal attitudes and values,” a 2004 decision said. “You tend to minimize your criminal offending by claiming to be just the pilot. … Your offending relates to your poor decision making, the lure of easy money and your entrenched criminal values.”

Mr. Boulanger finally left prison in 2013, 20 years after his conviction. He emerged as a celebrity, with TV appearances and his book. “He walked around this building like he was a rock star,” said Anne Roy, who befriended him as a neighbour in the Montreal loft building where they both lived.

“He was rough around the edges but he had a kind soul,” she said. As time passed and Mr. Boulanger was fighting blood cancer, he became more of a recluse, living alone with his cat, called Casey. During the pandemic, he became virulent in his views against masks and vaccines and a bit of a conspiracy theorist. “He thought it was the government’s way of controlling people,” Ms. Roy added.

“He had more lives than a cat,” said his eldest daughter Amber Shute, who now lives in Victoria, where she’s a clinical herbalist. “He was pretty cocky and wasn’t short of self-confidence.”

Amber’s mother, Jane Thompson, was Mr. Boulanger’s second wife. When Amber was child, he was frequently away and her parents had a volatile relationship. They split up when Amber was 7. Amber stayed in touch with her father while he was in prison and would see him in Montreal after he was released. She said her father always got along with people, even in prison. “He was friendly, very entertaining, full of stories and people generally liked him.”

But she concluded, “He was a complicated man to have as a father.”

Mr. Boulanger leaves his daughter, Amber; his son, Faron; and one grandchild. His three marriages ended in divorce.

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