Mere days before his arrest last February, Ismael Habib, the 29-year-old Quebecer on trial for terror-related charges, confessed to an RCMP undercover agent that he'd whipped a prisoner while in Syria — and that he knew of young Muslims in Montreal who were "hot" to go overseas.

Those were among the confidences Habib shared with the agent, known to him as "the Boss," in a Mr. Big-style sting operation that involved at least six undercover agents in Montreal earlier this year.

The Boss took the witness box for a second day Thursday at Habib's trial before Quebec Court Judge Serge Délisle at the Montreal courthouse. Habib is charged with attempting to leave Canada to commit terrorist acts and giving false information to obtain a passport.

Like the other two undercover officers who have testified for the Crown so far, the Boss's identity is protected by a publication ban, and he is testifying from behind a screen.

The Boss explained he had been earning Habib's trust over the course of months, by hiring him for odd jobs. 

Charles Montpetit

The lawyer representing Ismael Habib, Charles Montpetit, leaving a Montreal courtroom in November 2016. (CBC)

Muslim radicalization in Montreal?

The Boss testified he had been given a package including compromising photos, letters and a USB key featuring a video where Habib is seen whipping a prisoner while he was in Syria.

Over a meal in a Montreal shopping mall, he asked Habib to explain the contents of the package and to tell him what he knew about radicalization in Quebec.

The Boss said he pressed Habib about whether others from Canada wanted to travel to Syria.

Habib mentioned two mosques, including the Assahaba Mosque in Montreal's east end, where he said some young Muslims were "hot," or willing to go.

He also mentioned one imam at the Assahaba Mosque who he said was "preaching" to youth, though it was unclear if he meant the imam was preaching radicalization.

What happened in Turkey?

In November 2013, Habib had his passport seized in Turkey, but the details of exactly what happened had been murky until this point, four days into his trial.

The Boss testified that Habib confessed to him that on his trip to Turkey, he spent some time in Syria. He said he liked it: where he was, he told the agent, people were relaxed, they smoked and hung out together.

Habib told him his problems began when he went back to Turkey to be with his wife and children, the Boss testified. That's when he was sent back to Canada, via Calgary.

Lyne Décarie

Crown prosecutor Lyne Décarie in the Montreal courthouse in November 2016. (CBC)

Video whipping prisoner

The Boss testified that when he asked Habib about the contents of the video, the man said it was shot in Syria, where he whipped a Syrian prisoner because, he told the agent, the prisoner had been incarcerated for raping a woman.

Habib told the Boss he wasn't a violent man, that his priority was his wife and children.

According to the Boss's testimony, Habib hadn't been a member of ISIS when he was in Syria, however, after his return to Canada, he had come to the conclusion that it was his "duty" to fight jihad alongside ISIS.

"Everyone else was not a real Muslim," the Boss testified.

passport

Undercover operation at Montreal's Old Port

The Boss also testified about an undercover operation at Montreal's Old Port that preceded his shopping mall food court conversation with Habib.

He said on February 9,  two agents — the Boss, and another agent whose cover story was that he was trying to leave the country — met Habib at the Old Port to help the second agent get onto a boat leaving Canada.

The Boss testified he told Habib he could bow out of the operation at any moment he felt uncomfortable, but instead, he said, Habib seemed to be very pleased with what was happening, albeit a little nervous.

The court has heard from several witnesses, including the Boss, who said Habib was fixated on obtaining a passport to leave the country to be with his wife and two children.

He'd told some undercover agents he wanted to meet them in Algeria, but the Boss testified that Habib told him he planned on going to Syria.