Mayor Rob Ford faces possibly the most critical day in a career full of them, when a stumble or misguided belief could help launch him out of office less than halfway through his term.

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“I imagine he’s had this day circled in his calendar for a while,” Myer Siemiatycki, a Ryerson University politics professor and city hall watcher, said of Ford’s scheduled testimony Wednesday on a conflict-of-interest complaint from Toronto resident Paul Magder.

Related: Read Ford’s June 27 deposition

“The stakes are high — as Ford himself has acknowledged, it could spell the end of his mayoralty.”

Ford will be cross-examined by Magder’s renowned lawyer, Clayton Ruby, and defended by Alan Lenczner, who is less known to the public but regarded by colleagues as one of Toronto’s top litigators.

Ford is adamant that he was right to speak and vote on the question of whether he should return $3,150 in donations that lobbyists, their clients and a private company made to his private football foundation.

Related: Read Royson James’ take on the proceedings

“I actually believe I have done nothing wrong,” Ford said on CP24 last week, adding he doesn’t understand why he should pay out of pocket when the donations bought equipment for needy kids. He has also dubbed the case against him “all politics.”

Related: The major players in Rob Ford’s conflict of interest case

Siemiatycki said he can’t fathom how Ford doesn’t realize it wasn’t right to solicit money from people actively lobbying him on city business.

“In a way, the sadder and more troubling piece to this saga is that, we’ve all made mistakes, but the depth of Ford’s inability to recognize that he has erred is pretty astonishing,” he said.

Here’s a look at the case:

• The charge: Ford is accused of breaking a provision of the Municipal Conflict of Interest Act that states elected officials can’t speak to, or vote upon, items in which they have a “pecuniary interest.” The integrity commissioner in 2010 ruled then-councillor Ford was wrong to use his letterhead and other city resources to solicit donations for his namesake charity from people lobbying him. Council agreed and ordered Ford to repay $3,150 to lobbyists, their clients and one private firm. Ford ignored six reminders from the integrity commissioner and, when it came back to council in February, made an impassioned speech about why he shouldn’t be forced to repay the money. He then voted with the 22-12 majority to rescind the order that he do so.

• The defence: In his factum, or summary of defence, Lenczner argues the Municipal Conflict of Interest Act does not apply to council’s Code of Conduct, which Ford was deemed to have broken when it ordered him to repay the money. Lenczner also argues council never had the right to make the repayment order. If that fails, Ford’s “alternative defence” is that the sum involved is “inconsequential” when weighed against his salary and the consequences of the Act, and that he made an error in judgment.

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The outcome: The judge can find Ford: not guilty, guilty of conflict of interest through inadvertence or an error in judgment; or guilty of knowingly breaching the Act. If the judge finds the latter, he has no option but to order that Ford be removed from office, and discretion only on whether to bar him from running for elected office for up to seven years. If Ford is removed from office, the city could either call a mayoral byelection or appoint a replacement from city council ranks.

Related: Details of Rob Ford’s closed door grilling.