Toronto is entering the strangest and most unpredictable period in its modern political history after a judge's ruling to expel Mayor Rob Ford from office. Will the expulsion withstand a court challenge? If so, will there be a by-election, and could Mr. Ford win it?

No one can answer these questions with certainty – although I have a few guesses – but let's take a look at what a certain U.S. defence secretary called the known unknowns.

Will Mr. Ford win his bid for a stay on the ruling ousting him?

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The case comes before a judge on Wednesday. A stay would allow the mayor to remain in office until an appeal court hears the case in January. Without a stay, the order removing him would take effect next Monday, when a 14-day delay on the application of the original ruling runs out.

The mayor got some good news on Monday when the man who brought the original complaint against him, Paul Magder, said he would not oppose the mayor's bid for a stay. Mr. Magder's lawyer, Clayton Ruby, said a stay would give the city "a measure of stability, something that has been wholly absent during Mr. Ford's term in office."

My guess: Mr. Ford gets his stay.

Would he win at appeal?

Higher court judges would need to find a serious error in the original ruling to overturn it. That is a tall order. Mr. Justice Charles Hackland of the Ontario Superior Court took 11 weeks to render judgment. His 24-page ruling goes through each of the mayor's defences at length and dismisses them one by one.

Mr. Ford's lawyer, Alan Lenczner, has signalled he will argue that Judge Hackland made at least two mistakes: first when he determined that city council was within its rights to order Mr. Ford to pay back $3,150 in improperly raised football-charity donations; second when he ruled that Mr. Ford did not make an honest error in judgment when he voted and spoke on the issue at city council last February.

My guess: He loses his appeal.

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Would city council appoint a mayor or call a by-election?

The City of Toronto Act says it can do either. Most city councillors seem to be leaning toward a by-election, giving voters, instead of the courts, the final judgment on whether Mr. Ford's offence was severe enough to warrant his removal. That seems like the right call. Appointment would mean that the city would be without an elected mayor until the next scheduled election, Oct. 27, 2014, a long stretch. Of course, council could always just reappoint Mr. Ford, who was elected with 47 per cent of the vote in 2010. Judge Hackland has made it clear that nothing in his ruling prevents Mr. Ford from holding office again, despite his removal. But simply restoring Mr. Ford to his job would stick in the throats of many councillors.

My guess: by-election.

Who would win a by-election?

Ah, now there's the $64,000 question. Speculating on political outcomes is unwise at the best of times, and this is a more unstable time than most. That has not stopped commentators from having a go. Broadcaster John Tory, the former Ontario Conservative leader and a candidate for mayor in 2003, says he thinks that Mr. Ford could win, corralling the right-of-centre vote and sticking to his message of fiscal responsibility. City Hall blogger John Michael McGrath disagrees. He looks at recent polls, including one by Angus Reid that showed two-thirds of respondents think the judge's decision to remove Mr. Ford was right. He concludes that while the mayor is holding onto his core supporters, he has lost many of the other centrist voters who supported him in 2010. That sounds right to me.

My guess: Mr. Ford loses.

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So: Mr. Ford wins his stay, loses his appeal then loses a by-election. That's my bet. Like any bet, it could be all wrong. An appeal court might find Mr. Ford really did make an error of judgment and let him keep his job.

Council could simply reappoint him on the grounds that the penalty was too severe for the infraction. Or it could install a caretaker mayor, deciding it would be costly and unreasonable to plunge voters into two elections for mayor in two years.

The next few weeks or months promise to be a wild ride.

It is fun to speculate how it will all turn out, but impossible to say.