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Councillor Doug Ford filed his nomination papers to run for mayor of Toronto on Friday after his brother withdrew.Fred Lum/The Globe and Mail

Can he win?

In some ways, he's his brother's polar opposite: a teetotalling, red-meat avoiding extrovert. In most other respects, there's no mistaking Douglas Bruce Ford, Jr. for anyone but the mayor's brother.

It's there in the pin-striped bravado, the bluster, the unstinting allegiance to family and fiscal conservatism. As a rookie councillor, he had sweeping influence. He was the face and mind behind key political battles, such as the fate of the Port Lands and the standoff with Chief Bill Blair. While he is often characterized as a more polished, less controversial version of his brother, history suggests otherwise.

But which Doug Ford will Toronto voters see? Can the rookie councillor, burdened by his own distinct political baggage, inspire the same inscrutable devotion among portions Toronto electorate as his brother? Will a tide of sympathy for the ailing mayor lift him to victory?

Recent polls suggest both scenarios are unlikely. A May Forum Research Poll put his support at 20 per cent, four points fewer than the mayor's, whose own odds of victory were considered long before he pulled out of the race on Friday.

The same poll put Doug Ford's approval rating at a paltry 30 per cent, two points shy of his brother's and a daunting 38 points behind John Tory, the widely acknowledged front-runner.

"Doug Ford simply doesn't connect as well as his brother," said Lorne Bozinoff, president of Forum Research. "He's seen to have a heavier hand in council."

That's not to say he can't improve. Rob Ford earned such animosity in the city over his four years as mayor that few pollsters could see him moving beyond the 30 per cent threshold. Doug Ford's popularity ceiling is unknown, according to Mr. Bozinoff.

"I do expect a honeymoon period," Mr. Bozinoff said. "There's a sense of family tragedy. I would imagine the Ford Nation block will transfer in the short run. If he starts at 28 and has 12 points to close in six weeks, that's doable."

That aligns with the one hard rule everyone involved with Toronto politics has learned over the past four years: "The one certainty about mayoral politics today is that nothing is certain," said Josh Matlow, a rookie councillor who started work at City Hall the same day as Councillor Ford and watched the elder Ford brother exert a back-slapping, browbeating influence across the entire city.

While Mr. Ford did not respond to requests for comment on Friday, his political biography is well known. His dad was an Ontario MPP and family friends included Mike Harris and Jim Flaherty, but Councillor Ford spent his first 45 years in decidedly apolitical pursuits.

A Globe and Mail investigation last year detailed how the future city councillor and aspiring mayor trafficked in large amounts of hashish during the 1980s. He repeatedly denied the allegations and vowed to serve the paper with a notice of libel, but never did.

In the 1990s, he travelled to Chicago and opened the Chicago office of the family business, Deco Labels & Tags. It was in the United States that he said he honed the jocular salesman's posture that would later characterize his early political reviews.

His business touch has never fully translated on the political stage. While his brother, for all his personal foibles, inspired a profound, almost familial psychological connection with voters, Councillor Ford's attempts at a common touch appeared ham-fisted and insincere on numerous occasions.

Early on in the term, there was his public feud with Margaret Atwood over the value of Toronto's libraries, during which he complained his ward had more libraries than Tim Horton's. He was accused of "corrupt and corrupting" behaviour by a fellow councillor for handing out $20 bills to constituents. He reportedly accused a group home for young adults with autism of destroying an Etobicoke neighbourhood and labelled its residents as having "violent tendencies." On live radio, he referred to the mayor's wife as a "Polack."

He careened from promise to promise without following through: a monorail, a Ferris wheel and an NFL football team.

And he bombed at building relationships. He has labelled members of the press gallery variously as "lazy," "the most biased person in the City of Toronto" and "jihadist." Facing a defamation suit, he apologized – twice – for accusing police chief Bill Blair of leaking information involving an ongoing investigation into the mayor. Even members of the mayor's staff were appalled at his treatment of council colleagues. "He was half the problem with Rob's agenda stalling," said a former staffer in the mayor's office. "Doug is a bully. Rob isn't a bully unless he's drunk or high. Doug is a bully … Councillors don't have time for that. They found it offensive."

His political opponents are already exploiting these miscues. "[He] has repeatedly put down the members of city council, who were his colleagues," said John Tory of Mr. Ford. "He has publicly disparaged the premier of this province and members of this cabinet. He has been insensitive to a number of our communities, including very recently the parents of children with autism. So I don't think Doug Ford is more of the same, in fact he may offer Toronto something that is worse."

But, in highlighting the divisions, Mr. Tory could be playing into Mr. Ford's hands. Voters sided with Rob Ford in 2010, "as a vehicle for punishing city hall, for poking elites in the eye," pollster Nik Nanos said. "It's what the Ford family represents … I'd say Doug Ford's chances are better than Rob Ford's. Beyond that, we don't know what will happen."