In late August nothing was going right in George Smitherman's bid to become mayor. The papers were full of scandalous stories of Rob Ford's arrest for drunk driving and drug possession, but his popularity only seemed to be growing.
The Smitherman camp had invited Liberal pollster Michael Marzolini, architect of Premier Dalton McGuinty's majorities, to diagnose what ailed the troubled campaign. During one Marzolini focus group, a middle-aged woman explained that she would overlook personality failings in a mayor - as long as he didn't waste her taxes.
"It was the most powerful thing I'd ever seen," recalls campaign manager Bruce Davis. "People knew [Mr. Ford]had these character flaws. They knew all that …"
And, by all appearances, they didn't care.
This revelation should have been an omen of what was to come: the felling of Ontario's powerful former deputy premier by an unlikely municipal renegade wielding a simple message.
From the start, Mr. Smitherman's team suffered from being a "big tent" affair with myriad advisers from across the political spectrum. His strategists knew the election was fast becoming a referendum on Mayor David Miller's approach to governing, set against a backdrop of economic uncertainty and irritation over tax hikes and political perks. Polling data showed the city was deeply split over Mr. Miller's record. But Mr. Smitherman and his brain trust couldn't decide which side of the urban divide they wanted to win over. When they finally placed their bets, it was too late.
In many ways, Mr. Smitherman put himself at a disadvantage from the outset, says Ryerson University politics professor Myer Siemiatycki: He played a quiet, cagey campaign early on, let his opponents set the agenda and failed to adequately set himself apart afterwards.
"He needed to more pointedly and directly try to puncture the assumption that the city was totally broken down and in need of a major overhaul. Because once he conceded that, he could not win ... He could not sell himself as the better fixer."
On a flight home from Florida in early January, Mr. Smitherman took out a pad of paper and started scribbling ideas about what he wanted to do as mayor.
The famously combative, intensely partisan Liberal had first hinted at a run during last year's garbage strike, with a showy bid to clean up the city. A few weeks later, Mr. Miller announced he wouldn't seek re-election, leaving the field wide open. Before long, a clutch of Mr. Smitherman's long-standing advisers - including Tory strategist Jaime Watt, Liberal adman Gordon Ashworth and NDP pollster Bob Penner - began meeting. It was late November, 2009, and most observers expected he would be taking on radio host John Tory.
Upon his return from Florida, Mr. Smitherman arranged to meet Bay Street lawyer Ralph Lean, a top political fundraiser, at the King Edward Hotel on Jan. 8. Mr. Lean, who had planned to back Mr. Tory until he pulled out, was now looking for a place to park his support. Over breakfast, Mr. Lean told Mr. Smitherman he had two major concerns - spending and transportation - and that he'd be interviewing Rocco Rossi later that morning.
The two men had history: In the mid-1990s, when Mr. Smitherman was former Toronto mayor Barbara Hall's executive assistant, they'd butted heads over the Air Canada Centre (Mr. Lean represented the Raptors). "For two years I worked with him, fought with him and yelled at him," said Mr. Lean. They emerged from that encounter with a mutual regard.
After breakfast ended, an emboldened Mr. Smitherman marched up to City Hall and, with the media looking on, registered to run. Afterward, he took what looked suspiciously like a victory skate on the rink in Nathan Phillips Square.
Through the early spring, Mr. Lean and his network had little trouble generating cash for the campaign among Liberals and downtown Tories.
Inside Mr. Smitherman's Esplanade headquarters, things were proceeding less smoothly. While his advisers wanted to keep plenty of cash on hand for the final innings, he came under fire for running a low-profile, idea-free campaign - a phase that came to be known internally as "the phony war." Some critics said he was reprising Barbara Hall's disastrous 2003 run, but Mr. Smitherman dismissed the parallels. "Campaigns are about the future," he said, "not the past."