Rob Ford entered the mayoral race as a man known for courting two things: fiscally conservative voters and controversy.
Since then, he's won over more of the former and avoided the latter, executing a disciplined campaign that propelled him into first place in the most recent poll.
But now a taped phone conversation in which Mr. Ford offers to help an ill man "score" the powerful painkiller OxyContin "on the street" is raising fresh questions about whether the councillor has the judgment to lead Canada's largest city.
Mr. Ford, in turn, is accusing the man who taped the exchange of setting him up, saying he only suggested buying illegal narcotics to get rid of an agitated caller who knew where Mr. Ford and his wife and two young children live.
"This man, when he was on the phone, clearly stated ... that I'm looking at your house," Mr. Ford told a news conference Thursday. "... when your family's threatened, that's where I draw the line."
The Etobicoke councillor filed a formal complaint of criminal harassment with Toronto police on Wednesday - one day before a story appeared in a local tabloid and nearly two weeks after the June 4 call.
A spokeswoman for the campaign said alerting police had nothing to do with looming media attention and that Mr. Ford contacted police by phone Tuesday to lay the groundwork for a complaint.
During the 52-minute conversation, Dieter Doneit-Henderson, an HIV-positive gay man who also has the chronic pain ailment fibromyalgia, asked Mr. Ford if he could get him OxyContin, a painkiller often abused as a street drug.
"I'll try buddy, I'll try," the councillor replied. "I don't know this shit, but I'll fucking try to find it."
A few moments later Mr. Ford asked: "What does OxyContin go for on the street, so I have an idea?"
Earlier in the discussion, which revolves around Mr. Doneit-Henderson's difficulty persuading 10 different doctors in Toronto to prescribe him the cocktail of painkillers he says he desperately needs, Mr. Ford asked, unprompted: "Why don't you go on the street and score it [OxyContin]"
But toward the end of the call he said he doesn't "know any drug dealers at all" and that he would "bet his life" he won't be able to procure the drug illicitly.
The surreptitious recording surfaced less than a week after a Nanos poll for The Globe and Mail, CTV and CP24 put the penny-pinching councillor ahead of George Smitherman for the first time, though just barely.
Myer Siemiatycki, a municipal politics expert at Ryerson University, said the recording could wound Mr. Ford's campaign.
"This does go to one of the main question marks about Councillor Ford: Does he have the judgment, the maturity, the balance to show good judgment at all times on behalf of the city?"
Ironically, Mr. Ford's new troubles began when he tried to lay an old controversy to rest.
The councillor met Mr. Doneit-Henderson May 10 when he went to the apartment Mr. Doneit-Henderson shares with his husband, Colville, to apologize for saying in 2006 that, "If you are not doing needles and you are not gay, you wouldn't get AIDs probably."
By the end of the visit - which was photographed and reported in the Toronto Star - Mr. Doneit-Henderson talked of volunteering for the Ford campaign.
In an interview Thursday, Mr. Doneit-Henderson said his affection for Mr. Ford stemmed largely from a promise to help sort out his medical troubles. When Mr. Ford failed to deliver, Mr. Doneit-Henderson taped the June 4 conversation and eventually turned it over to the Toronto Sun.
Mr. Doneit-Henderson, frail and clad in a striped bathrobe, denied threatening Mr. Ford. He only mentioned the potential to view Mr. Ford's nearby home from his 19th-floor apartment in passing, not as a threat, Mr. Doneit-Henderson insisted.
"He's, of course, turned this around to make it sound as if we're somehow stalking him or standing outside his home," Mr. Doneit-Henderson said. "It's just absurd."
According to the recording, which Mr. Doneit-Henderson provided to The Globe, Mr. Doneit-Henderson said: "I'm being completely, completely deserted. I look out my window, I see Lake Ontario. I'm looking south ... you know I can actually see your house from here?"
"Yeah, you've got a nice view from there, I know," Mr. Ford interjects. At no time does Mr. Doneit-Henderson explicitly threaten Mr. Ford or his family.
The caller does, however, grow more agitated as the call progresses, swearing about the doctors and politicians he claims have failed to help him, including Liberal MPP Donna Cansfield. Mr. Ford said she has also filed a police complaint about Mr. Doneit-Henderson. Ms. Cansfield could not be reached.
Mr. Ford spends most of the conversation patiently listening to the caller and trying repeatedly to end the conversation with gentle parting lines like "leave it with me."
The whole affair was simply a "good deed" gone wrong, the councillor said.
"I will never regret doing my best to help someone in need," Mr. Ford said. "Yes, I feel that I've been set-up. There are people out there who will do anything in their power to make sure I'm not mayor of this great city."