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Alex Hundert, 31, pled guilty in November to counselling to commit mischief and counselling to obstruct police in connection with protests outside the G-20 leaders' summit two years ago.Michelle Siu/The Globe and Mail

When he co-founded an anti-war group at Wilfrid Laurier University five years ago, Alex Hundert gave some direction to a previously aimless life. He grew up middle-class in Toronto, was booted from preparatory school for poor attendance as a teen and spent most of his early 20s partying hard and bumming around ski hills in British Columbia.

In committing himself to radical politics, however, he also put himself on a path that would eventually lead to his arrest on conspiracy charges before the G20 summit. On Tuesday, the summit's second anniversary, Mr. Hundert will go to prison after pleading guilty to reduced counts of counselling to commit mischief.

Police and prosecutors have portrayed Mr. Hundert, 31, as a ringleader of the mayhem on the streets that weekend. It's a characterization he's uncomfortable with: The concept of a leader is anathema to the anarchist movement of which he was a part.

"I think it's a question of what we mean by leader," says Mr. Hundert, wearing a black baseball cap over a long ponytail tied at the nape of his neck. He's sitting on a concrete ledge on the back porch of a Toronto house where many of anti-G20 protests were planned. "Did I have any authority? No. Did I exhibit leadership? Sure."

That question – to what extent the G20 riot was organized ahead of time – has been central to the case. While officials maintained Mr. Hundert and his cohorts met to plan the chaos in which police cars were torched and windows smashed on the streets, activists insist authorities misunderstood non-hierarchical organizing techniques. To them, the riot was the result of many groups and individuals deciding to act out.

In his earlier life, it would have been difficult to imagine Mr. Hundert planning much of anything. He says he was expelled from prestigious Upper Canada College, then from North Toronto Collegiate Institute. He graduated from Oakwood Collegiate Insitute and, after a brief stint at the University of Toronto, headed to Whistler, B.C., where he spent three years skiing and working as a bouncer and a cook.

One New Year's Eve, he was hit by a truck while crossing the road during a snowstorm. The collision broke his femur, forcing him to stay in bed for months. He eventually decided to go back to school.

Gradually, he fell into activist organizing in his spare time, getting involved in on-campus politics at Wilfrid Laurier University and participating in fundraisers.

In 2007, he co-founded Anti-War at Laurier, known widely as AW@L. This group and the Southern Ontario Anarchist Resistance, of which he was also a member, were infiltrated by undercover police officers posing as activists. On the morning of the primary day of protests, Mr. Hundert and several others were arrested and charged with conspiracy to commit mischief.

Much of the Crown's case against the group revolved around a meeting surreptitiously taped by an undercover officer the night before. While there are references to property destruction, no one can agree on what will actually happen the next day.

"Are we consenting to have no plan?" one facilitator asks near the end of the meeting, to cheers of approval.

Syed Hussan, who was arrested as part of the same alleged conspiracy but whose charges were later dropped, said the point of the meeting was to share information. Decisions on whether to break windows or confront police were made on the streets by small individual groups, not centrally co-ordinated, he said.

And despite the infiltration by police and the arrests of the alleged ringleaders, the riot still happened.

"They gathered some intelligence, they couldn't understand the rest of it, they arrested a whole bunch of people," Mr. Hussan said. "Yet, another very large community of people still did what it wanted to do."

Mr. Hundert said he believes the case against the group was politically motivated, designed to discourage others from confrontational protests.

"It's obviously about the politics," he said. "One of the ridiculous things, one of the infuriating things, is they keep insisting that it's not."

Mr. Hundert and his co-accused were released on bail conditions placing some under house arrest, prohibiting them from attending protests and communicating with each other. Last fall, shortly after their preliminary inquiry had begun, prosecutors offered to negotiate.

Mr. Hussan said that, at first, the Crown simply told them they wanted a certain number of people to plead guilty and take a certain amount of jail time. Prosecutors had another condition: they would not accept a plea deal unless everyone -- including accused ringleaders like Mr. Hundert and fellow activist Mandy Hiscocks -- were part of it. Mr. Hundert made sure it was written into the deal that he would get to choose his sentencing date.

"I realized I had a couple of chips left and I played them," he said.

Mr. Hundert said that, since the case never went to trial, it's difficult to say what, exactly, he and others did wrong. He admits to helping to create a "target list" of places that would be appropriate for protesters to converge. He said he knew some of the locations on the list -- which included banks, police stations and political offices -- would be vandalized, but never specifically instructed people to do so. He also led a workshop teaching people how to de-arrest other protesters.

"I'm sure I did something illegal," he says. "But no one can tell you exactly what it was."

Mr. Hundert pleaded guilty to helping to create a "target list" for a group called the Toronto Community Mobilization Network. The list included names and locations of banks, police stations, political offices and other locations in Toronto that would be appropriate for protests. He says he knew some of them would be vandalized, but never specifically instructed people to do so.

He also led a workshop teaching people how to "de-arrest" other protesters, including by surrounding them and pulling them away from a police officer on the street.

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