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Mayor Rob Ford’s appeal will be heard Monday. If he loses, council has to call a by-election or appoint an interim mayor.Deborah Baic/The Globe and Mail

Faced with the sobering prospect of being ejected from his own game, Mayor Rob Ford has expressed what he's now hoping will happen after his conflict appeal is heard in Courtroom 3 at Osgoode Hall on Monday. "Hopefully I'll win the appeal," he told Newstalk 1010 last week, "and if I don't, then [hopefully] I get appointed."

No mayor in Toronto's modern history has had to harbour hopes like those. And no council has faced the kind of uncertainty that now pervades city hall.

On the eve of a court hearing that could change everything, councillors insist they are focused on pressing city business, such as the 2013 budget, the casino consultation and the hobbled state of the Gardiner. But the rancour and rampant speculation about the political fallout has become impossible to tune out. "The tone of the dialogue is just so toxic," sighed Trinity-Spadina councillor Mike Layton, "I can't imagine a place that's worse than this."

In November, Justice Charles Hackland lobbed a legal grenade into city hall when he ruled that Mr. Ford should be removed from office for breaking a conflict-of-interest law intended to prevent council members from participating in debates and votes on items in which they have a "direct or indirect" financial stake. Mr. Ford cast a vote last February during a council debate over whether he should be compelled to reimburse $3,150 in donations to his family football foundation solicited from several registered lobbyists and firms doing business with the city.

If the divisional court upholds Justice Hackland's ruling, its decision will be final, said municipal lawyer Ron Kantor. (A court official said Friday the appeal panel will be Regional Senior Justice Edward Then, Justice Lynne Leitch and Justice Katherine Swinton.) Barring further legal machinations, Mr. Ford would have to relinquish the chain of office. Should council decline to appoint Mr. Ford back to office, these events will trigger a leadership vacuum on council that could take months and possibly millions of taxpayer dollars to resolve.

The background

The case traces back to a run-in between Mr. Ford and Toronto integrity commissioner Janet Leiper. During a 2010 investigation, she concluded that he had used city staff and council letterhead to solicit donations from registered lobbyists, thereby running afoul of council's code of conduct.

During the final session of Mr. Miller's term, in August, 2010, council backed Ms. Leiper's recommendation to fine Mr. Ford. But as mayor, Mr. Ford has refused to comply, despite attempts by Ms. Leiper to enforce the decision. She wrote to him seven times asking whether he had yet reimbursed the funds.

She submitted a follow-up report in council last February, again recommending that he return the money. During the debate, Mr. Ford denied ever handling the funds. He voted as part of a majority on a motion to reverse the August, 2010, decision to impose the fine.

Paul Magder, a Toronto IT manager, launched the court action after reading a news report about the debate. The ensuing trial took place over two days in September, and featured a long and often torturous cross-examination of the mayor, who seldom sits still for questions from the media. The fact that Mr. Ford didn't seek to have the courts overturn the original fine and subsequently ignored Ms. Lieper's entreaties provided Mr. Ruby with considerable legal ammunition to characterize the mayor as contemptuous of the laws governing council.

That line of argument took. In his November ruling, Justice Hackland criticized Mr. Ford's "dismissive and confrontational attitude to the Integrity Commission and the Code of Conduct." He allowed that the legal penalties for conflict-of-interest charges were harsh, and perhaps ought to be reformed by the Ontario legislature at some later date. Still, in Justice Hackland's view, Mr. Ford broke the rules as they currently exist, and did so with a certain recklessness. "In my opinion," he wrote, "the respondent's actions were characterized by ignorance of the law and a lack of diligence in securing professional advice, amounting to willful blindness."

The players

The watchdog: Janet Leiper is a prominent Toronto criminal and administrative lawyer who was appointed as integrity commissioner in 2009 for a five-year term. She's taught at Osgoode Hall and is a former chair of Legal Aid Ontario.

The instigator: Paul Magder filed the complaint because he was concerned about Mr. Ford's apparent disdain for council's rules. He also has a long-standing family friendship with left-leaning activist Adam Chaleff-Freudenthaler, a one-time school trustee candidate who launched a challenge of Mr. Ford's campaign finances and has been involved with this case. Asked to react to Justice Hackland's decision last fall, Mr. Magder told reporters, "It's a sad day, really, but it's got to be done."

The star lawyer: With a long track record in criminal cases and political advocacy, Clayton Ruby is virtually a household name in Canada. During cross-examination, he repeatedly forced Mr. Ford to admit he paid almost no attention to the laws and codes governing elected officials. "He should have played by the rules," Mr. Ruby said after the ruling was handed down. "Rob Ford did this to Rob Ford."

The sharp-eyed defence counsel: Alan Lenczner is widely regarded in legal circles as one of Canada's savviest commercial litigators. Over a decade ago, former mayor Mel Lastman retained him to negotiate a deal with the computer firm involved in a notorious procurement scandal that led to the creation of the city's code of conduct and lobbyist registry.

The judge: Based in Ottawa, Justice Charles Hackland was selected to hear the original case specifically because he's an outsider. Seen as a bold, thoughtful jurist, he has presided over high-profile political cases, among them, a lawsuit brought by former Tory cabinet minister Helena Guergis against Stephen Harper, which the judge saw fit to toss out.

The legal arguments

While Mr. Lenczner has challenged four aspects of Justice Hackland's ruling, the linchpin of the case before the Divisional Court is that the lower court failed to acknowledge that city council, back in August, 2010, did not have the legal authority to order Mr. Ford to reimburse the $3,150 to the original donors.

In a 34-page factum submitted before Christmas, Mr. Lenczner argued that everything that followed from that original ultra vires decision is, therefore, moot, including the results of the council session last February during which Mr. Ford cast the vote that started the whole process.

Mr. Lenczner also asserted that Justice Hackland didn't apply the "error in judgment" defence correctly, and that he misinterpreted the City of Toronto Act. The 2006 law says council "may" impose "either" a reprimand or fine of up to 90 days' salary on councillors who violate the code of conduct. Mr. Lenczner's brief said that language precludes other penalties, such as Ms. Leiper's order for Mr. Ford to repay the $3,150.

He stated that Justice Hackland should never have imposed the harsher penalties in the Municipal Conflict of Interest Act – among them removal from public office – given that the relatively small donations to Mr. Ford's football charity had no bearing on the city's operations.

But Mr. Ruby flatly rejected those arguments in his 49-page brief, which stressed the mayor's admitted habit of ignoring the rules and procedures governing councillor conduct. Taking direct aim at Mr. Lenczner's contention that legal experts have criticized the blunt instrument of Ontario's conflict rules, Mr. Ruby stressed that the mayor's defence "is based on the law as he wishes it to be, not as it is."

What's next

While it took Justice Hackland over two months to hand down his verdict, the Divisional Court is expected to rule more quickly.

If Mr. Ford loses the appeal, provincial rules say that council has 90 days to decide whether to call a by-election or appoint an interim mayor. During this transition period, deputy mayor Doug Holyday will be responsible for day-to-day decisions.

If council opts for a by-election, it will likely take place in the spring, with an expected cost of as much as $9-million. Some councillors are balking at the expense. Others, such as Mr. Layton, argue that a by-election is necessary . "I do think we need to have a mayor and it's likely the people of Toronto should be the ones to determine who that is."

However, a by-election is no guarantee the Ford era will come to a close – the mayor, who garners about 42 per cent support in recent polls, vowed yesterday that "I'll be running in the next municipal election."

Several names of prospective challengers are circulating, including that of NDP MP Olivia Chow, as well as councillors Adam Vaughan, Karen Stintz and Shelley Carroll, the only declared candidate so far. "It won't be a stop-gap election," said Ms. Carroll. "People will be looking at someone they can live with for the next five years."

The appointment option, though less expensive and less disruptive, is fraught with complexity because prospective candidates would have to garner the support of a large majority of council to lead effectively. Names like John Tory and former mayor David Crombie have been bandied about.

If the division court tosses out the decision, Mr. Ford will return to his post. According to veteran political strategist John Duffy, a former adviser to Paul Martin, it's unlikely Mr. Ford will benefit from a sudden groundswell of renewed support. "I have trouble envisioning a sustained, powerful 'the boss is back' moment."

And, Mr. Duffy noted, the mayor still faces another legal hurdle – a forensic audit of his campaign finances, which will be presented to council's compliance audit committee in early February. "The bigger question is what happens if the election spending item moves into crisis pitch on the heels of this [appeal]."

None of the options hold much appeal for Mr. Duffy, who argued that the drama around Mr. Ford's legal problems have proven to be hugely distracting for a council facing major problems, such as modernizing the transit system. "There is no scenario where I can see the kind of stability and leadership at city hall that we need to deal with the challenges that are upon us."