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Michael Zehaf-Bibeau was described as well-liked in high school, although he flirted with trouble. But, years after high school, he began to sell and consume hard drugs, including cocaine, a former friend said. ‘Drugs changed him.’

While Michael Zehaf-Bibeau sank into misery, his faith in Islam growing along with his drug addiction and psychological torment, his estranged father was living it up.

Around Montreal's Crescent Street bar strip, people describe Bulgasem Zehaf as a baby boomer bon vivant who owned a bar, drove a Porsche and partied like a man half his age.

Every day, more details emerge on the tattered adult life of Mr. Zehaf-Bibeau, the 32-year-old Ottawa shooter who slid into criminality and homelessness. He had cut most ties with his divorced parents: his mother, Susan Bibeau, who had risen to the top ranks of the civil service, and his father, who had multiple business interests and shuttled between Montreal and North Africa.

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A federal government source said Friday that Ms. Bibeau is now on leave from her job as a deputy chair at the Immigration and Refugee Board. Acquaintances say Mr. Zehaf has been in Tunisia in recent months and continues to run a vehicle import and export business he established in Canada. In a statement, both parents expressed anger at their son over the shootings, and declined to be interviewed.

It also emerged Friday that Mr. Zehaf-Bibeau attempted to get a Libyan passport on Oct. 2, but was turned away by Libyan embassy authorities who were suspicious of his demeanour and his reasons for wanting to travel to the country. Federal bureaucrats were holding up the dual citizen's attempts to get a Canadian passport over security concerns.

Reports that his father made his own trip to his native Libya in 2011 to fight against Moammar Gadhafi raised questions about whether father and son may have sought to join jihad. Mr. Zehaf's friends laugh at the suggestion, saying he was never religious and was more likely looking for a chance to make money.

Mr. Zehaf, known to Montreal friends as Bello, owned at least two Montreal eating and drinking establishments in addition to the car business.

"He owned a bar, he sold liquor, he was a guy who liked to hit the clubs, he drank," said Ahmed Chouaya, a 32-year-old Montrealer of Tunisian origin who grew up with Mr. Zehaf-Bibeau and calls his father a friend. "His dad was not a man who had anything to do with any jihadi tendencies, believe me."

A female friend of the father from the first decade of the 2000s who hung around his bar Café Tripol put it succinctly: "It was just yee-haw party time."

The son had been well-liked in high school. But even then he was dabbling in the sale of soft drugs, and he frequently faced detentions at school, according to the friend and classmate, who asked to remain anonymous.

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But it was the years after high school that marked a turn toward both the sale and consumption of hard drugs, including cocaine, the friend said. His moods took sharp and at times violent turns.

"Drugs changed him," the former friend said. "He could be happy one minute, then go ballistic the next." The friend recalls a house party at which Mr. Zehaf-Bibeau got high and began to fight. "He put his fist through the wall. He could lose it and would get paranoid."

The friend went regularly to Mr. Zehaf-Bibeau's house, located in a middle-class neighbourhood. "His father wasn't around much," the friend said. "He was with his mother, and his mother worked a lot, and he was left alone a lot. He had a lot of freedom."

Eventually, Mr. Zehaf-Bibeau headed west, clashing with the law along the way. In 2011, he was arrested after attempting to rob a Vancouver McDonald's with a pointy stick.

"I want to come to jail so I could clean up," Mr. Zehaf-Bibeau told the judge, according to court transcripts released Friday. "I'm a crack addict and at the same time I'm a religious person, and I want to sacrifice freedom and good things for a year maybe so when I come out I'll appreciate things in life more and be clean."

He also tried to confess to a 10-year-old Montreal armed robbery in an attempt get help through more prison time. "The RCMP member tried to help him but could not find any record of any such armed robbery and therefore refused to arrest him," the prosecutor said.

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Two years later, on Oct. 2, when Mr. Zehaf-Bibeau arrived in Ottawa, he went to the Libyan embassy to renew his passport. He told officials he wanted to visit siblings and friends in Libya, where he'd last travelled in 2007. Mr. Zehaf-Bibeau, whose father is Libyan, was issued a Libyan passport in 2000.

"His general demeanour was not appropriate just judging from the way he was dressed, the way he was behaving, his body language was not appropriate. That led … them to doubt his character – his motivations," said first secretary Yousef Furgani through a translator.

Mr. Furgani asked him questions about his parents. Mr. Zehaf-Bibeau told officials his parents were divorced and that he wasn't in regular contact with either of them.

When told it would take three weeks or longer to process his application, Mr. Zehaf-Bibeau dropped the matter. He never returned.

With reports from Patrick White in Ottawa, Sean Gordon and Nicolas Van Praet in Montreal and Mark Hume in Vancouver

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