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Anti-summit protesters clash with police in downtown Toronto June 25, 2010 during the G20 summit.

Kevin Van Paassen

In early 2009, two strangers started mingling with the activist communities of Kitchener-Waterloo and Guelph.

The first was a man. Those who crossed paths with him say he ingratiated himself by chauffeuring people to protests in his white van and buying them pitchers of beer at the bar after. The second, a woman, told people she had fled an abusive relationship, acquaintances say.

Both were undercover police officers infiltrating organizations planning protests against the Toronto G20 summit in June, 2010. They were part of the Joint Intelligence Group, an RCMP-led squad with officers seconded from the Ontario Provincial Police and other forces, whose task was to gather information on threats to the summit.

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The probe, which lasted a year and a half, would fail to prevent the smashed windows, burning squad cars and 1,100 arrests for which the summit would become known. But it did end with 17 people accused of conspiracy to commit mischief. For at least some of them, Tuesday is expected to be judgment day.

Court proceedings so far are covered by a pretrial publication ban; a separate court order prohibits disclosing undercover officers' identities. But The Globe and Mail interviewed activists over the course of several months and examined public documents to glean a sense of the depth of the infiltration.

Anti-poverty activist Julian Ichim, for instance, came to regard the male officer as his best friend, and recalls him helping out Mr. Ichim's cancer-stricken mother, driving her to and from hospital during her dying days. The female officer, meanwhile, went so far as to share a home on a quiet residential street in Guelph with some of the people she was spying on, activists say.

Police forces involved in the JIG would not comment on specific details of their undercover operations. Ontario Provincial Police Sergeant Pierre Chamberland said of the riot: "You have information, you get intelligence and all these kinds of things, but individual behaviour is unpredictable."

Both Sgt. Chamberland and a spokeswoman for the RCMP said undercover officers are bound by rigorous internal policies.

RCMP records obtained under Access to Information indicate the force's JIG had 12 undercover operatives focus on groups that "indicated a propensity toward violence and other criminal activity."

But it was the two officers in Southwestern Ontario who brought in the highest-profile case.

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Activists' first recollections of the male officer are from the winter of 2009, when he attended meetings of Limits, a group opposing the construction of a business park near Hanlon Creek in Guelph. His story, they say, was that he worked at a dry storage company in Kitchener and had a young daughter from a previous relationship.

Mr. Ichim first got to know him at an anarchist book fair in Hamilton on June 6, 2009. Mr. Ichim, a fervent communist, was arguing with young anarchists over Che Guevara and the man jumped in to defend the Argentine revolutionary.

The officer, Mr. Ichim said, told him his family was from Kenya and had been involved in that country's independence struggle, and displayed an impressive knowledge of radical history. He said his new friend also liked to drink and flirt with women.

"He was energetic, outgoing," Mr. Ichim said. "He was a good listener, he'd ask you about issues in your personal life. He seemed like a really good guy."

Some of those who knew the female officer, meanwhile, say they sympathized with the middle-aged woman, who seemed to be going out of her way to make friends with people much younger than she was.

"[She]appeared to be this socially awkward woman who didn't have many friends," Guelph activist Kelly Pflug-Back said. "I always felt like I needed to reach out to her."

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Ms. Pflug-Back said she visited the woman's Guelph apartment once, before the officer moved in with other activists, and recalled it seemed sparse and unlived in.

That summer, protesters set up a makeshift encampment at the proposed site of the Hanlon Creek Business Park. The male officer was there, Mr. Ichim said, and pushed for radical action.

"[The officer]was saying 'we need to take monkey wrenches and [damage construction]machinery,'" he said. "The occupation had a lot of support and he was talking about wrecking machinery, which tactically makes no sense."

(Sgt. Chamberland said officers can break the law, but only with "prior, specific" permission from higher-ups.)

The undercover officer had a tendency to play up divisions between activists, they said, such as by telling Mr. Ichim that student protesters were insulting him behind his back.

The male officer also joined student activist group Anti-War at Laurier. Member Dan Kellar remembers the man also drove people around to dumpster dive and socialized.

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"Always buying pitchers of beer for everyone, making sure to drive people home," Mr. Kellar said. "He was befriending us by just being really helpful and then buying lots of alcohol."

On Jan. 2, 2010, the male undercover was arrested during an unsuccessful attempt to block the Olympic torch relay at a bridge near Espanola, Ont., according to two protesters who were there. They said the officer transported people and barricade-building materials in his van.

"We could never have done the action without him," said lawyer Davin Charney, who provided legal support that day.

Protesters were unloading it when police swarmed them. Everyone was released without charge half an hour later at the side of the highway.

The officer also bolstered his credibility by having people over to his apartment, on one of the roads into Guelph, said Mr. Ichim, whom the officer also introduced to a man he said was his cousin, visiting from India. They had lunch at a Mississauga steakhouse and discussed the Indian government's crackdown on Sikh activists in 1984, Mr. Ichim recalled.

Both undercover officers joined the Southern Ontario Anarchist Resistance, or Soar, a group organizing G20 protests, members of the group said. The male officer eventually aroused suspicion when he turned up at a meeting to which he wasn't invited and he was kicked out of the organization. The female officer remained trusted until the end.

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On the morning of June 26, 2010, hours before black-clad protesters stormed through the heart of Toronto, police swooped in to arrest many of the activists who knew the undercover officers.

At a show-cause hearing that day, prosecutors told court about the investigation. By the time Mr. Ichim got out of prison two days later, he was resigned to the fact that one of his closest friends had been a cop.

"I kept on calling his phones and leaving messages," he said. "'Look me in the eye, explain why you did this.'"

In the months that followed, Mr. Ichim had his charges dropped, while other people were added to the case.

Activism has become harder to organize, with the fear of infiltration keeping many away. Both Mr. Ichim and Mr. Kellar, who was never charged with conspiracy, say they have subsequently been charged with violating the publication ban for writing blog posts about the undercover officers they believed were their friends.

The investigation's subjects say it also affected them on personal level.

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"You go through something like that, and how are you supposed to trust another person again? How are you supposed to approach people honestly without being suspicious of them when you've had an experience like that?" Ms. Pflug-Back said. "That's sort of a really surreal situation that no one really wants to imagine themselves in."

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