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Mayor John Tory speaks to a member of the public after holding a media scrum in front of city hall in Toronto, on Sept. 11, 2018.Christopher Katsarov/The Globe and Mail

Lawyers for the City of Toronto are delving into uncharted legal waters for ways to challenge Ontario Premier Doug Ford’s plan to use the Constitution’s notwithstanding clause to cut city council almost in half with six weeks to go before a municipal election.

The Progressive Conservative Premier has recalled the legislature for Wednesday to reintroduce a bill that would reduce Toronto’s council to 25 wards from 47 after an Ontario Superior Court judge struck it down on Monday for violating the Charter of Rights and Freedoms. Mr. Ford’s move has created confusion over deadlines for nominations, and even some incumbents are concerned they might be unable to run under the new system after Mr. Ford enacts his constitutional override, which could take days.

Council will meet in a special session on Thursday to discuss what legal avenues, if any, the city has to challenge the provincial government. Mayor John Tory, who met with Prime Minister Justin Trudeau on Monday evening to discuss the matter, acknowledges any legal battle against the notwithstanding clause would be steeply uphill, but says city lawyers have been told to look at all possibilities.

“From what I can see, there are very, very limited options open to us,” Mr. Tory told reporters on Tuesday. “… But I haven’t taken any option off the table.”

Legal experts say lawyers for the city and the candidates could revive their arguments from their court challenge of the legislation that Mr. Ford’s bill violated “unwritten constitutional principles” of democracy and rule of law. They could also try a rarely attempted legal argument based on a 1988 Supreme Court of Canada case on Quebec’s use of the clause. In that case, the court deemed that the notwithstanding clause cannot be used retroactively to erase a past breach of the Charter.

Mr. Trudeau said on Tuesday that Ottawa would not stand in Ontario’s way.

“We are disappointed by the provincial government in Ontario’s choice to invoke the notwithstanding clause, but I won’t be weighing in on the debate on how big Toronto’s municipal council should be,” he said.

On Monday morning, an Ontario Superior Court judge struck down Mr. Ford’s first attempt at the Better Local Government Act, which is known as Bill 5 and was passed on Aug. 14 with the campaign well under way. In his ruling, Justice Edward Belobaba declared that the move violated the free-expression guarantee in the Charter by changing the rules mid-campaign. He also said the new, much larger wards violated Toronto voters’ rights to “effective representation.”

Just hours later, the Premier announced he would use Section 33 of the Charter, known as the notwithstanding clause, to override the ruling, and threatened to use it again if judges strike down other legislation.

Mr. Ford is also appealing the ruling, and seeking a stay that would render it void. If the province files its notice of appeal imminently, a hearing could come as soon as Friday. The city and legal teams for council candidates have vowed to fight both the stay and the appeal.

Mr. Tory said he is confident that concerns that some incumbent councillors will be unable to run in the election would be resolved.

The original Bill 5 extended nominations for council to Friday. But once the law was struck down on Monday, the city’s election reverted to its 47-ward system, for which nominations closed in July, and the clerk’s office refused to accept nominations for the 25-ward system.

A number of mostly left-leaning councillors, including Joe Cressy from downtown and the west-end’s Gord Perks, had refused to sign up for the 25-ward system, but were planning to do so by Friday. If Mr. Ford’s new legislation does not change the deadline, some at city hall fear that could leave those councillors off the Oct. 22 ballot.

The Ford government will table an amended version of Bill 5 on Wednesday afternoon that will invoke the notwithstanding clause and could contain other changes. Government House Leader Todd Smith’s office would not confirm what further amendments are expected.

A bill at Queen’s Park requires about eight to 10 days to become a law, and Ontario’s Legislature is only expected to sit for four days over the next two weeks, with next Monday and Tuesday off to allow MPPs to attend the International Plowing Match and Rural Expo near Chatham-Kent.

With a report from Robert Fife