Montreal police moved quickly Saturday to crack down on an annual protest that has a history of getting out of hand.
A crowd of demonstrators gathered outside a busy north-end subway station to denounce police brutality.
It was the same location where, this past January, an officer was captured on video telling a homeless man he would tie him to a pole for an hour in the freezing cold if his behaviour didn't improve. The officer was disciplined for his actions.
The man who filmed that incident, Adis Simidzija, was on hand for the protest.
Simidzija, a 25-year-old university student, said he's still disturbed by what he saw, and the way police handled the student marches during Quebec's so-called Maple Spring two years ago.
"We're here to protest against the police brutality we saw in the 2012 student protests, and that we see every year," Simidzija said.
Organizers said they wanted to bring awareness to what they described as racial and social profiling, along the targeting of homeless people.
But the demonstration didn't last long.
Using a loudspeaker, police declared it illegal within minutes because they weren't provided with an itinerary, as required under a municipal bylaw.
Helmeted officers on bikes and horseback, and later in riot gear, forced many of the protesters onto a side street and surrounded them.
In all, more than 280 people were detained and each was given a $638 ticket for breaking the bylaw, according to police.
Another five people were arrested and two people suffered minor injuries.
Shortly after 7 pm, four hours after the demonstration began, the last of the tickets were still being handed out, said police spokesman Ian Lafreniere.
A portable toilet was made available for protesters awaiting their release, he said.
The spokesman said the annual protest is always difficult and that he's "proud of the police officers" for making the best of a difficult situation.
"It's impossible to have a win-win situation," he said.
"We're never winning. When you're talking about protest like that, it's sad."
Aside from a vandalized news truck and police vehicle, there were few signs of the troubles that have marked previous editions of the protest.
A demonstration against police brutality has been held in Montreal for the past 18 years. Many of them have ended in violent clashes between protesters and police.
In some years, the protest has led to a number of smashed-in storefronts and damaged cop cars.
More than 200 people were arrested at last year's protest, which was also cut short by police.
Felix Gamache, a 19-year-old college student, said he didn't even get a chance to join Saturday's demonstration.
Gamache and his friend arrived shortly after it began, and were cut off from other protesters by a line of police.
"I think, first of all, we have a basic right to protest," he said.