The 16th edition of the tension-packed march was marked by much the same mayhem as witnessed in previous years: looting, vandalism and clashes preceding mass arrests.
An exasperated Gerald Tremblay said Friday he is ready to "evaluate all options available" to deal with protesters in the future.
He said he was disgusted by the sight of protesters running amok on city streets Thursday night, saying such behaviour hurts Montreal's reputation.
"My tolerance is at its limits," the mayor told reporters. "This is the case for all Montrealers."
Montreal police said 226 people were arrested during the raucous protest.
Police chief Marc Parent said 36 people were nabbed in isolated arrests, while 190 were detained in a mass roundup at a street corner near the downtown core.
Four people were still in detention on Friday and were expected to be arraigned on charges including assault, possession of a weapon and breaking conditions.
Parent said dealing with the annual anti-police protest is always complicated and poses particular challenges.
"In English they say "damned if you do, damned if you don't," Parent said of any police decision to move on the crowd.
Parent said he wasn't satisfied that the protest quickly went sour, but praised the work of officers.
Seven officers were slightly injured, as were two civilians who tussled with protesters, he said.
But eyewitnesses also saw demonstrators who were injured, including at least one man who was cut by an exploding stun grenade.
The police chief commended the work of officers, calling their actions "professional" as they confronted projectile-tossing protesters.
Some in the crowd also vandalized stores and smashed two cop cruisers, including one that was flipped over on its roof.
Authorities responded by firing off chemical irritants in a bid to disperse the estimated 1,000 people.
Police said Friday the number may have peaked at between 1,500 and 2,000 before the crowd broke off into several splinter groups.
Police have been overwhelmed with nearly daily protests by striking students protesting tuition hikes. There are more to come, Parent noted.
"In the last weeks and in the coming weeks also we have a lot of demonstrations and it's very important (for the groups) to collaborate with the police to make sure it will be done in a safe way," Parent said.
"We know disruption is part of the message, but we want to be there to help them to make sure they're doing it safely."
Tremblay said offering protesters plenty of leeway and the opportunity to make their voices heard in a safe and secure way simply has not worked.
"We're still in a lose-lose situation,'' Tremblay said. ''If we don't do anything, we're criticized; if we try to do prevention, we're criticized; and when there's violence or mischief, we're criticized.
"We can't continue like this."
The Collective Opposed to Police Brutality, which organizes the annual march, criticized the police's decision to declare the protest illegal 30 minutes after it started.
It said police "prevented the event from following its intended path and must therefore be held responsible for this turn of events." It was a route the group refused to share with police.
The group says it was collecting information on many alleged cases of police heavy-handedness.
Police were doing the same.
On Friday, they announced that video and photos sent to them by the general public could lead to other arrests.
A similar tactic used by police in Vancouver following the Stanley Cup riot last spring resulted in arrests.
"We will use those videos and we do say 'merci beaucoup' for (the) citizens who have done that," Parent said.
Parent said he was particularly amazed at how young some of the protesters were Thursday night.
"I think there were people there who were acting in good faith and had a message they wanted to share with other citizens, the government," Parent said.
"But there are always people who will take advantage of this situation to create havoc, to agitate, to provoke the situation and commit criminal acts, destroy private property and our equipment."