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Toronto mayoral candidate George Smitherman is seen while campaigning on Oct. 5, 2010.

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."

CAMPAIGN BEGINS

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."

From the start, Mr. Smitherman's basically centrist instincts posed a challenge for his campaign. Some advisers, citing an early internal poll showing surprisingly strong support for Mr. Miller and the progressive approach, argued for a left-leaning campaign. Others wanted Mr. Smitherman to lean right, promising, for example, to privatize garbage collection.

"There was lots and lots of debate and probably a lot of it wasn't all that useful," said one strategist. "At one level, there were just far too many advisers in the tent. George knows a lot of people. There were just a lot of people around."

After a long career in politics capped by two senior stints in Mr. McGuinty's cabinet, Mr. Smitherman approached the task of getting elected much as if he was running a large ministry.

He came up with dozens of ideas, demanding crisp, bullet-proof work-ups that would become policy planks. "He asked millions of questions, sometimes to the frustration of the policy people who said, 'George, we don't have a paid staff,' " recalls one senior adviser. Among other things, Mr. Smitherman, thinking like a minister, wanted to make sure city bureaucrats knew what awaited them when he took office. But they weren't the audience he needed to convince.

In April, Mr. Smitherman - notorious for his outbursts at staff - jettisoned campaign manager Jeff Bangs and replaced him with Mr. Davis, a well-connected school trustee who'd run Mel Lastman's winning effort in 1997. Officially, Mr. Bangs left because the campaign was soaking up too much time. There may have been other factors. "The scuttlebutt," says one volunteer, "was that George blew up at him one too many times." But by then, Mr. Ford was changing everyone's calculations.

SUMMER

Hershell Ezrin, a veteran Liberal strategist who gave Mr. Smitherman his first job in politics, joined the campaign, and he vividly remembers the feedback the canvassers were picking up at events or on doorsteps. Everyone had absorbed Mr. Ford's waste mantra. "They could all recite the plant-watering story," says Mr. Ezrin of Ford's website reference to the city spending $77,000 a year on that job. "You could see that Mr. Ford's messages were resonating."

The Smitherman camp, determined to stay in the daily news, was cranking out vast quantities of detailed, and occasionally obscure, platform policy through a complex network of committees and informal advisers that included prominent figures like former Chrétien cabinet minister David Collenette, planner Ken Greenberg, theatre director Albert Schultz, blue-chip Rosedale fundraisers (Isabel Bassett and Heather Peterson), investment bankers and city finance experts.

Some of it proved too complicated by half, such as Mr. Smitherman's scheme for using public-private partnerships and a "transit trust" to build subways, based on a financing formula the province had used to build hospitals. The campaign's communications team struggled to explain the concept, and was forced to revise its numbers shortly after releasing them.

Using dedicated researchers, the team also began to turn its attention to the business of discrediting Mr. Ford. They launched one website showcasing the councillor's outbursts (FordonFord.com), and another, based on Barack Obama's "Fight the Smears" site, that sought to counter Mr. Ford's bald allegations about Mr. Smitherman's profligacy as health minister.

On the eHealth scandal, some advisers advocated a keynote speech where Mr. Smitherman would correct the record on his role - a gesture he ached to do. Others nixed the idea. "There's an adage in politics that if you're explaining, you're losing," says one strategist. "I know his explanation and it's credible. But how do we re-fight that battle and come out a winner?"

By July, recalls Mr. Davis, "We had a very strong signal that we were 20 points behind."

Efforts were made to expose Ford's voting record on service cuts, like snow-shovelling for seniors. "We knew we were going to have to take the gloves off or we were done," says Mr. Davis. "But none of that stuff worked."

AUTUMN

When Mr. Smitherman launched his campaign in early September, his "recalibrated" image (a waste fighter who'd freeze taxes for a year and personally lead a search-and-destroy mission for fiscal flab) reflected Mr. Marzolini's assessment of the problem: Mr. Ford's rap sheet didn't matter because the groundswell behind him was "like a 1960s protest," he said.

"To take on Rob Ford, you have to take him on in his environment."

He urged Mr. Smitherman to revisit the pugilistic persona he'd cultivated when the Liberals were in opposition. "When you're going up against Ford," Mr. Marzolini said, "you have to be yourself."

Mr. Marzolini admits he never set foot in Mr. Smitherman's campaign office, and his advice bothered some strategists who felt the candidate was abandoning his natural centre-left constituency in a bid to out-Ford Mr. Ford.

The public wake-up call came in late September, when a Nanos poll conducted for the Globe and Mail/CTV/CP24 revealed that Mr. Ford had opened up a gaping 24-point lead. (Conducted shortly after Mr. Smitherman's relaunch, that poll came within 1.3 percentage points of predicting Mr. Ford's final share of the total vote.)

Deputy campaign manager Sean Hill, an NDP organizer and former Joe Mihevc aide who joined the team mid-summer, recalls the phones in Mr. Smitherman's HQ started ringing almost immediately, bringing the volunteer recruitment effort, which had been moribund for months, to life. He recalled the following day's edition of the Toronto Sun, which featured a large photo of a smiling Mr. Ford and the headline, "Toronto's Next Mayor."

"That woke everyone up."

With veteran Liberal organizer Tom Allison leading the so-called "ground war," Mr. Hill and other campaign workers began focusing on tactically important neighbourhoods, such as Port Union or Mount Dennis, where they could persuade residents to consider the implications of Mr. Ford's proposed cuts. As Mr. Hill said, "People would say, 'I might actually lose something that matters to me.' "

With organizers scrambling to identify supporters and persuade them to put up lawn signs, Mr. Smitherman and his strategists continued to grapple with the vexing question of defining their man. Some campaign materials presented him as Toronto's first gay mayor and others outlined his plan to freeze taxes and cut waste.

On the hustings, Mr. Smitherman increasingly set aside Mr. Marzolini's recommendations and talked up his "progressive" values and positive vision, messages reinforced by a parade of high profile endorsements, mainly drawn from Toronto's well-heeled political class and Mr. Smitherman's cabinet contacts.

Behind the scenes, Smitherman emissaries were pressing some of Rocco Rossi's key supporters - the candidate personally lobbied some high-profile Liberals, like Ray Heard, to make the switch. Mr. Smitherman even left a voice-mail for Mayor Miller. According to chief of staff Bruce Scott, Mr. Smitherman wanted the mayor to urge Joe Pantalone to bow out, as Sarah Thomson had done. Asked about the call, Mr. Smitherman said, "I thought it would be helpful at that stage to get his perspective." Mr. Miller, who'd been on the receiving end of Barbara Hall's back-channel efforts to elbow him out of the 2003 race, never returned the call.

LAST DAYS

By the final weekend before the election, Mr. Davis's e-day team had managed to recruit more than 1,500 volunteers to pull the vote and work the phones. But while the campaign team had been buoyed by Mr. Smitherman's improved polling numbers through October, his strategists were still fighting fires at the 11th hour.

After an anti-poverty ethnocultural coalition gave him high marks for his positions on diversity, for example, mass e-mails started bouncing around the Jewish community saying Mr. Smitherman was being endorsed by a Muslim organization with apparently strident anti-Israel views. The campaign had to respond by distributing photocopied flyers to members of the Jewish community, reiterating Mr. Smitherman's support for Israel.

On Saturday, Mr. Smitherman, a driver and two campaign aides raced around the city in a last-minute blitz of glad-handing and mainstreeting. As he was driven from Etobicoke to the Beach, Mr. Smitherman's spokesperson, Erika Mozes, handed him her BlackBerry to show him the translation of an ad running on Tamil radio that alluded to his sexual orientation.

As he scrutinized the e-mail and murmured his disapproval, Mr. Smitherman's car was stuck in a traffic jam that clogged streets throughout the west end. After talking endlessly about his "days of disruption" plan to alleviate gridlock, gridlock, ironically, was forcing him to cancel campaign stops on the fly.

"City's big," he declared, as the vehicle crawled through side streets. "Holy lord, it's big. You think you know the city well, and then you run for mayor …."

Special to the Globe and Mail, with a report from Anna Mehler Paperny

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