Doug Ford’s art of the deal: What is he pitching to Ontarians and will they buy it?

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“Patrick Brown never pulled in numbers like this,” one supporter tells me, as more than 200 people file into Thunder Bay’s historic Finlandia Club. It’s early April, the sun is out and there are triangle tuna sandwiches at the back of the fluorescent-lit room. Once a meeting place for revolutionary Marxists, the hall’s big draw tonight is Doug Ford Jr., the former label salesman that Ontario’s Progressive Conservatives have entrusted to return them to power in the June 7 provincial election, after almost 15 years in opposition.

Thunder Bay hasn’t elected a Progressive Conservative to Queen’s Park in more than 30 years. Those in the room feel their city has stagnated under Liberal rule and see Mr. Ford – whom they regard as a brash, shoot-from-the-hip fiscal conservative with a stellar business record – as Thunder Bay’s path back to glory.

“The population here has been steadily declining in the last 10 years and I’d like to hear how he’ll put a stop to it,” says Andrew Christie, who runs an office-supply business in the region. “This current government has been spend, spend, spend, but we haven’t seen the benefits.”

Mr. Ford seems to feel the weight of their expectations – he promptly flubs his opening, telling the crowd they have a great local candidate in Derek Parks, who’s running in Thunder Bay-Superior North, before proceeding with his speech. One problem: There are two provincial ridings in Thunder Bay and two PC candidates. The one he missed – Brandon Postuma – happens to be the tallest man in the hall. Many eyes turn to his disappointed face.

The rest of the speech is trouble-free. He speaks without notes for half an hour. The pitch is by now familiar to anyone paying attention to the election campaign: Turf Liberal Premier Kathleen Wynne, cut taxes on individuals and businesses, fire the CEO of transmission utility Hydro One (“the $6-million man”), cut electricity rates, balance the budget (eventually), erect a neon sign at the U.S. border declaring “Ontario is open for business.”

He talks of being open and accessible. His campaign slogan is “For the people.” All standard conservative fare, with more than a dash of grievance-tempered populism. The sentiment contains strong echoes of his brother’s successful 2010 Toronto mayoral campaign, which Doug co-managed, and during which the brothers fomented anger against the political establishment with a simple two-slogan appeal: Respect for taxpayers. Stop the gravy train. Rob Ford’s resounding victory gave credence to the idea that the brothers were impresarios of anger. That they could tap into it, shape it, channel it.

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While that may have been true of Rob, whose mere countenance projected a disgruntled everyman disposition that mirrored much of Toronto’s suburban electorate, Doug, the salesman, has struggled to adopt the same persona and close the deal.

He took the stage that evening in Thunder Bay with a 17-point lead in the polls. Last week, that lead collapsed to nil. Pollsters have recorded a strong migration of support away from Ms. Wynne’s Liberals and toward Andrea Horwath’s New Democratic Party in a strategic move by voters to elect anybody but Mr. Ford. A Conservative campaign designed to knock out Ms. Wynne is now swinging at air as it pivots to take on Ms. Horwath.

For the most part, the cratering of support has been a surprise. But even back in April, there were indications of voter trepidation to come.

“What did you think?” I ask Mr. Christie, the business owner, after the speech.

“I was hoping for a little more,” he says.

“A little more what?”

“Substance.”

With the election now days away, Mr. Ford remains the candidate most likely to form the next government, in part because of the geographical distribution of the anti-Liberal wave. But questions linger about who he is and how he would govern.

And he has yet to deliver a lot in the way of details. When the party finally released its plan on Wednesday, it consisted largely of proposed rate cuts and big spending promises, with little suggestion of how he would pay for them, short of running big deficits.

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In a way, Doug’s entire adult working life has been built on eschewing complexity and embracing superficiality. After attending Scarlett Heights Collegiate Institute in Etobicoke, in west Toronto, he enrolled in business administration at Humber College. Within weeks, as he would recall in his 2016 memoir, Ford Nation: Two Brothers, One Vision, he was “bored silly in the lectures.” Worse, the college had no sports program, robbing him of an opportunity to relive the athletic glories of high school, where he’d played football and hockey. (High school also marked a period when he’d sold hashish, according to a Globe and Mail investigation in 2013. Mr. Ford still denies the allegation and originally said he would take legal action. He has yet to do so.)

After two months at Humber, Mr. Ford abandoned his studies. “All in all, college was pretty disappointing after how much I’d loved high school,” he wrote.

And so he put on a suit and went to work at his dad’s company, Deco Labels & Tags. There, Doug Ford Sr. initiated his namesake son by driving him to the front door of a commercial building in Toronto’s northern suburbs. “Okay,” said Doug Sr., “start dropping off brochures.”

It was 1984 and the son trudged up and down the building knocking on doors. He was hooked.

Every sales job is about selling yourself and Doug Ford Jr. became an adherent of self-help guru Dale Carnegie and his book How to Win Friends and Influence People. Where once he sported a shaggy blond mane, he now adopted the short, slicked-back style he maintains today, set off by custom suits and reinforced by a leased Lincoln Navigator.

“I loved the challenge of the cold call,” he writes in his book. “I loved being able to go out and sell a good product and offer people a service they might otherwise not be getting.”

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Mr. Ford wasn’t dragged into politics for his ideas or his considerable personal charisma. He was conscripted for his genes.

Doug Ford Sr. had served as an MPP for a single term, ending in 1999, with Mike Harris’s Conservatives. At Queen’s Park, the Ford patriarch earned a reputation as a heckling backbencher with personal values grounded in a fatherless, Depression-era upbringing. “He grew up poor and as a little boy went out, got jobs and slipped money under his mother’s pillow,” says John Parker, a fellow PC MPP, who would later serve on city council with the Ford sons. “Horatio Alger, that was him in a nutshell. No time for slackers or self-indulgence.”

Doug Jr.’s recruitment into elected office came in 2010 at an east-end Toronto Swiss Chalet. Rob had entered the mayoral race to great fanfare, but little in the way of endorsements. Doug sat down with city councillor Mike Del Grande, a hard-line fiscal conservative, to sell him on the idea of endorsing Rob for mayor.

“I call it the Chicken Summit,” says Mr. Del Grande. “My view was that Rob couldn’t go to City Hall alone, because he didn’t really trust anyone except family. I told Doug he had to go down there to watch his brother’s back.”

At first, Doug’s ego wouldn’t allow it. “He was telling me there was no way he wanted to be a city councillor,” said Nick Kouvalis (who would go on to become Rob’s chief of staff), talking to long-time city councillor John Filion for his 2015 book on Rob, The Only Average Guy. “It was too low of a position for him.”

At Mr. Del Grande’s urging, he relented. And then some. At age 46, Doug arrived at City Hall intent on turning the place upside down.

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For the previous 15 years, he’d run the family firm. In the industry, he had a reputation as a risk-taking businessman whose forays stateside were met with wild success and one notable failure. The former came into being in 1998, when, against his father’s wishes, he opened a company office in Chicago – which, more than a decade later, would generate roughly $11-million in revenue, according to a 2014 Globe and Mail investigation.

Then came the failure: In 2008, he bought a distressed company in Pennsauken, N.J., called Wise Tag and Label. His Toronto staff warned him to go slow. The acquisition soon became a headache and a drain on revenues at a time when the Great Recession meant Deco could ill afford it. Then, in 2012, Kevin Wise, a son of the company’s founder, filed a civil action against Doug in New Jersey Superior Court (a detail the PC leader did not acknowledge on his candidate questionnaire, which requests information on all past legal proceedings). Mr. Wise alleged that Doug had failed to pay him an agreed-upon sum of $179,654.27 related to unpaid loans, credit-card debt and compensation. (The lawsuit was dropped in 2016 following Mr. Wise’s death.)

In his book, Mr. Ford writes this of the Wise Tag experience: “If I had to do it all over again, I don’t think I would’ve bought out that business; I just would’ve started from scratch.” Deco parted ways with Wise Tag and Label last year, halting operations in May and selling the assets.

An impulsive, risk-taking approach would come to typify Mr. Ford’s years at City Hall.

When his brother passed him over for plum deputy-mayor and committee-chairs posts, he threatened to abandon politics altogether. “If you think I came down here just to be the councillor from Ward 2, you’ve got another thing coming,” he roared at one meeting, according to Unstoppable, a book by another of Rob’s chiefs of staff, Mark Towhey. “I’ve had it. I’ll just quit and go back to Chicago.”

Mr. Ford developed a habit of squiring his own guests through his brother’s office, conducting meetings in the mayor’s boardroom and sitting at the mayor’s desk to make calls, according to former staff, who began locking the office. “Then Doug got a key. From Rob. Who would complain when Doug used it,” writes Mr. Towhey. “It was nuts.”

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When they worked more unambiguously in concert, the brothers did not shy away from using intimidation to secure votes on council. “They thought they could actually bully people into supporting them,” Councillor Denzil Minnan-Wong is quoted as saying in The Only Average Guy. “They’d just go in and threaten that they were going to run people against them in their wards. ‘Better support us, or we’ll get Ford Nation to work against you.’ ” (Mr. Minnan-Wong is now one of Mr. Ford’s star candidates.)

Not that Mr. Ford was short of great big ideas. He had a propensity for talking strategy with friends into the wee hours – “the night shift,” the mayor’s staff called it – and then arriving at work the next morning, new plans in hand. Mr. Towhey writes that, after the 2010 election, Mr. Ford’s night shift expanded “to include former premiers and high-powered political operatives – none of whom had ever worked in a mayor’s office, with city council, or with Rob.”

One such plan materialized in August, 2011, when Mr. Ford introduced a proposal to build a giant Ferris wheel, monorail, luxury hotel and megamall on the city’s waterfront.

As brash and bold as the Fords themselves, the proposal’s half-baked provenance ensured it a quick death. For one thing, Waterfront Toronto, an agency jointly funded by the municipal, provincial and federal governments, had a plan in place for a new community and urban park on the same land. What’s more, Doug hadn’t bothered to notify his brother’s staff of the city-changing plan or to build support on council.

It was not the only fantastical pitch to come out of the Ford camp. That same year, Doug started soliciting private-sector proposals for a $4-billion extension of the truncated Sheppard subway line. Several councillors and city staff say he was particularly taken with a proposal from a Russian developer. “Doug was bugging me to meet with [the man], so I agreed,” says Peter Milczyn, then-chair of the city’s planning and development committee. But on the agreed-upon day, Mr. Milczyn’s daughter fell sick, requiring him to stay home. “This guy pulls up to my house in a Bentley,” recalls Mr. Milczyn. “He gives me a box of chocolates and asks me to set up meetings with the prime minister and premier.”

The pitch itself? In return for extending the subway line at no cost to the city, the developer would take excess dirt from the project, dump it at Downsview Park in north Toronto and develop a ski resort there. “I just laughed,” said Mr. Milczyn. “It was nonsense.”

As his thwarted ideas piled up, Mr. Ford began talking openly about returning to Deco full-time, or running provincially or maybe federally – the story seemed to change on a regular basis. When Rob was diagnosed with cancer six weeks before the 2014 municipal election, Doug replaced him on the mayoral ballot.

For months after losing that election to John Tory, Mr. Ford maintained a low profile, emerging occasionally to talk about his brother’s health and then his eventual death in March, 2016. Five months after Rob died and a publication ban was lifted on a long-reported video of him smoking crack, a combative Doug returned to the airwaves, calling the video’s release “disgusting.”

Next, he announced another mayoral run, putting Mr. Tory back in his crosshairs. Just five days before CTV would air allegations of sexual misconduct against PC leader Patrick Brown, Mr. Ford appeared at City Hall, accusing the mayor and council of waging what he called “war on the car” with a proposal to build bike lanes on busy Yonge Street. Asked by Mr. Filion, a chief proponent of the plan, if he’d read the bike-lane proposal, Mr. Ford answered: “I don’t need to read a staff report to see they’re going to destroy Yonge Street.”

“He can turn any question or accusation around,” says Mr. Filion, of Mr. Ford’s sometimes fearless disregard for the nuts and bolts of civic policy. “You can’t touch him. You can swing but you can’t land a punch.”

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In his city-hall days, Doug was caught on camera calling reporters a “bunch of pricks.” He referred to a female journalist as “a little bitch.” He labelled published facts about his brother’s substance abuse – which proved, in the end, to be debilitating – “Soviet Stalin-era Pravda journalism.” He taunted spectators at city council. He launched a publicly embarrassing weight-loss challenge for his brother. He made accusations against a police chief that brought a defamation notice.

Just a month after being elected party leader in March, it was clear that his tendency to fall back on unpolished rhetoric remained an issue. Asked about his decision to skip a leadership debate organized by black leaders in Toronto, Mr. Ford claimed that no politician in Canada, aside from Rob,had “supported the black community more than I have” and he openly snapped at another reporter who asked how tax cuts might benefit the family company.

When he did behave, his handlers could barely contain their relief. “Well done! Right on message!” campaign co-chair Dean French yelled from the back of the room after Mr. Ford delivered a faultless mid-April news conference to denounce the state of Ontario’s finances.

Around that time, Mr. Ford’s campaign brain trust, which includes several past advisers to former prime minister Stephen Harper, clamped down on media access to his public announcements. Most take place in hotel meeting rooms where security partitions keep reporters a good 15 feet from the candidate. At least once, a Liberal Party observer was forcibly removed by campaign staff. Mr. Ford reads prepared remarks from a Teleprompter, takes five or six questions and then promptly exits to the exuberant applause of his staff.

“Something happened when he was elected leader,” said Mr. Del Grande, the man who urged Mr. Ford to enter politics back in 2010. “There’s a whole big bureaucracy around him. I used to be able to call and he’d call right back. I’ve gone weeks without hearing from him.”

Perhaps no campaign appearance has better demonstrated Mr. Ford’s determination to vacuum-seal his public utterances than a recent stop in Tillsonburg, Ont.

Earlier that morning, the Liberals had released audio of what sounds like Mr. Ford and Kinga Surma, his preferred nominee for the riding of Etobicoke Centre, hawking free party memberships to patrons at a Tim Hortons outlet in the fall of 2016. “It doesn’t cost you anything,” Mr. Ford can be heard telling people, in contravention of party rules that require members to pay a $10 fee – and pay it themselves. The recording was accompanied by revelations made by Ms. Surma’s rival for the nomination, Pina Martino; she had tracked down 45 of Ms. Surma’s sign-ups who essentially told her their memberships were bogus. What’s more, said Ms. Martino, after she forwarded her findings to PC brass, Mr. Ford followed her home in his car.

Despite the unseemly accusations, at his podium in Tillsonburg, Ont., that day Mr. Ford did not pour fire on the flames with defensive bombast and stuck to his talking points. “This is the Liberals two weeks before an election trying to change the channel on their mismanagement, scandal and waste,” he said, before pivoting to talk of hydro rates and fuel taxes. As for Ms. Martino’s accusations about his tailing her, he said “that never happened,” adding that the party had cleared him of any wrongdoing.

So squelched was the brewing scandal that the issue didn’t even come up during the otherwise no-holds-barred final leadership debate three days later.

Watch: Liberal campaign co-chair Deb Matthews broadcasts the Ford audio

Despite the NDP’s surge of late, Mr. Ford remains the frontrunner in the race to become Ontario’s next premier, according to most polls, even though his core support has levelled off in the mid-to-high 30s, down from a mid-40s high in March.

And yet, it remains difficult for most voters to get a handle on him.

Two days after he promised voters “a very clear, costed platform,” the list of spending promises released this week failed to set out total projected spending and revenues under a PC government and did not say where Mr. Ford would find his long-promised $5.6-billion in spending “efficiencies.” Voters, said PC spokeswoman Melissa Lantsman, will not be given a full accounting before election day.

Mr. Ford’s statements on the hustings provide few clues about what lies ahead should voters hand him the keys to Queen’s Park. “I govern through the people,” he declared a few weeks back. “I don’t govern through the government.”

Over the past seven weeks, The Globe made 15 interview requests to Mr. Ford and various staff members. Never officially denied an interview, I was never granted one, either.

I did manage one real exchange with the candidate. It came that day in Thunder Bay, at a campaign stop in front of the Terry Fox monument. Mr. Ford approached me alone, following a short scrum he had held with the reporters of local news outlets. “I thought I recognized that face,” Mr. Ford said, extending his meaty right hand with a big smile. “How are you, buddy?”

“Yeah, it’s been a while,” I said. This was Dale Carnegie Doug, amiable Doug, the man most people meet when they meet Mr. Ford in person. The one I’d first encountered when I was a reporter in the early days of his brother’s mayoralty.

At the time, Doug was seen as the more conciliatory brother, the one who could act as a moderating influence on a mercurial Rob. He could be seen lunching with left-wing councillors – he always grabbed the bill first – and delivering birthday bouquets to fellow councillors who were, on any other day, his unadulterated rivals.

Or maybe conciliatory isn’t quite the right word.

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His mother, Diane, tells a story she uses to illustrate the personality differences between her two famous sons. As young boys, both kept messy rooms. Then one day, she issued an ultimatum: Clean your rooms or you’re grounded.

Rob took offence. “You’re always on my back about something, Mom!” he complained, according to Diane’s account in Doug’s Ford Nation.

Doug, she remembers, took a different tack. He hugged his mom and said, “I’m sorry. I know, I know. I really should have done it already.”

“That was Doug,” is how Diane put it. “Always the schmoozer, even as a kid. He could talk his way out of almost anything.”

At least, when he chooses to try. With little notice, even a Dale Carnegie acolyte can decide that making friends is not necessarily the best way to influence people. After we’d exchanged pleasantries that day in Thunder Bay, Mr. Ford held up his mobile phone, as if to imply that its contents held secrets about me, and said, “So I hear from people that you’re going after the Fords.”

I must have looked perplexed.

“Someone forwarded me an e-mail saying the Globe was sending you to go after us.”

“That is not at all what I’m doing,” I said. “I’m … ”

He interjected to tell me he had a friend connected to The Globe and suddenly began scrolling through his e-mails, presumably looking for proof of my ill will.

Then, he seemed to catch himself, as though remembering the redeeming power of positivity.

“But look, you can just call me or get in touch with me. I’m right here. Anything you want, buddy. Anything you want.”

With that, he turned on his heels and returned to an SUV where four handlers were waiting. I called after him to ask the best way to reach him.

He did not take my question.

With reports from Greg McArthur, Robyn Doolittle and Robert Fife

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