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What began as a scrappy, partisan website became a formidable vehicle for Tory support. But behind Ontario Proud’s homespun facade, there is big money and ties to professional party fundraisers

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Ontario Proud director Ryan O'Connor, left, walks with founder Jeff Ballingall in Toronto. Mr. Ballingall's company churned out anti-Liberal memes ahead of 2018's provincial election, targeting leader Kathleen Wynne as a 'clown,' 'scumbag' and 'corrupt.'Mark Blinch/The Globe and Mail

By the summer of 2017, Jeff Ballingall had hit the internet marketing sweet spot. His creation, a Facebook page called Ontario Proud, had built a loyal following of tens of thousands of users by tapping into two seemingly unrelated emotions: a fondness for sentimental images of Ontario landmarks, and rising anger with the provincial Liberal government, led by then-premier Kathleen Wynne.

What started as a lark in 2016 had turned into serious digital sway: an anti-Liberal meme machine that regularly pilloried Ms. Wynne and her cabinet for rising hydro rates and the province’s debt.

One year after launching his project, Mr. Ballingall incorporated Ontario Proud. He had become an official political influencer and the next stop on his journey was to get paid.

It started with small donations from like-minded Facebook followers, but by Aug. 2, 2017, he had attracted some real money. On that day, Mr. Ballingall sent an e-mail to Robert Faissal, a Toronto-based entrepreneur and a much sought-after Progressive Conservative donor. “I understand you’re expecting to hear from me,” Mr. Ballingall wrote. The two met in a parkette at Toronto’s luxury Four Seasons hotel, which led to Mr. Faissal cutting Ontario Proud a $10,000 cheque.

As for how Mr. Ballingall knew that Mr. Faissal was “expecting” him to reach out, Mr. Ballingall says he can’t recall. For his part, Mr. Faissal says he is certain who connected them: Alykhan Velshi, a well-known conservative political operative who was, at the time, chief of staff to the then-leader of Ontario’s Progressive Conservatives, Patrick Brown.

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Robert Faissal, shown in 2011.Della Rollins/The Globe and Mail

Election regulators have tried to discourage groups such as Ontario Proud from functioning as an end run for political parties skirting the caps on how much money they can accept – and Mr. Faissal says he was vaguely aware of these issues when he says he received a phone call from Mr. Velshi about Mr. Ballingall’s project.

“I told Alykhan ‘as long as it’s legal,’ ” Mr. Faissal said. “He’s like, ‘yep, it’s absolutely legal.’ ”

(When asked about Mr. Faissal’s account, Mr. Velshi called it “totally untrue,” but also acknowledged having met Mr. Faissal and telling “anyone who would listen” that Ontario Proud was the best thing to happen to the Tories.)

Whatever role Mr. Velshi played in the donation, if any, the suggestion that it was legal is correct – and that’s because his payment was made in a regulatory vacuum, one that all advocacy groups like Ontario Proud have used to their advantage in the months leading up to the federal election campaign announced this week.

When Prime Minister Justin Trudeau asked the Governor-General to dissolve Parliament on Wednesday, kick-starting Canada’s 43rd general election campaign, the political parties officially began their push to secure the most seats in the House of Commons. But for other kinds of parties – known officially in law as third-party political advertisers – the campaign merely marks the continuation of a persuasion war they have been waging for months and months.

Over the past few years, there has been a proliferation of special purpose groups, all created to denigrate either Conservative Leader Andrew Scheer or Mr. Trudeau, the heads of the two parties favoured to win the race.

Some groups, such as the anti-Scheer Engage Canada, which is primarily funded by labour unions, rely on traditional media, such as television advertising. Others, such as Ontario Proud – which has inspired a national version, Canada Proud, and sister “Proud” organizations in almost every province – depend more on organic, digital messaging. Ontario Proud and its affiliates have set their sights squarely on the federal campaign and Mr. Trudeau, using a combination of brash messaging, embarrassing photographs and pithy one-liners − “Trudeau is bananas” – to raise doubts about the Liberal Leader.

Regardless of form, these groups all have one thing in common: When they started fundraising and designing their attacks in 2017, 2018 and the beginning of this year, they did so under a cover of secrecy that Canada’s election law, as well as some provincial rules, affords them.

Canada’s campaign-finance rules, as well as Ontario’s, prohibit third-party groups from colluding with candidates and political parties to “circumvent” donation limits. But those laws only apply to a specified period of time – federally, it’s about two and a half months − before an election campaign is announced. Which means that, for the many months and years leading up to that point, such groups are effectively unregulated and free to raise as much money as they want, however they want.

It’s one of the many “troublesome” holes in the rules that was highlighted by Greg Essensa, Ontario’s Chief Electoral Officer, three years ago when he warned legislators about a rising wave of third-party influence.

“In contrast to parties and candidates, which are subject to limits,” third-party advertisers have the power to raise an unlimited amount of money, Mr. Essensa told the provincial standing committee on general government in 2016.

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Ontario Chief Electoral Officer Greg Essensa, shown in 2012.J.P. Moczulski/The Globe and Mail

Canadians, in general, regard their political battles as much more genteel than those fought in the United States, where super PACs − political action committees that advocate on behalf of certain individuals, parties or policies – raise and spend vast amounts of unregulated money to destroy the reputations of candidates they oppose.

But Mr. Essensa warned Ontario legislators that, left unchecked, the province could go down a similar road.

Among Mr. Essensa’s long list of concerns is how the law largely allows third-party advertisers to hide the identities of their funders – so long as they accept those funds outside the statutory reporting period, which for Ontario is six months before the writs are issued. Mr. Faissal’s donation is a case in point: He cut his cheque about 10 months before the provincial election, which means Ontario Proud had no obligation to disclose it to the regulator. Had Mr. Faissal not acknowledged to The Globe and Mail that he offered up this money, no one but Ontario Proud would know he was a major donor.

During the six-month period when Ontario Proud was required to disclose the contributions it received, it recorded about $489,000 in donations, the majority of which came from home builders and construction companies, corporations that are barred from donating to political parties.

As for how much Ontario Proud raised during the previous 20 months of its existence – and who contributed the funds – that remains a mystery. Mr. Essensa called on legislators to force disclosure of all donors regardless of timing.

For its part, Ontario Proud says it is not beholden to any particular political party and has gone so far as to issue libel notices to social-media commentators who suggest otherwise. “Whenever there’s a regulated period, we comply with the letter and the spirit of the law,” Ryan O’Connor, a director of Ontario Proud and its lawyer, said in an interview with The Globe.

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Mr. O'Connor, seen at right with Mr. Ballingall, says Ontario Proud's activities 'comply with the letter and the spirit of the law.'Mark Blinch/The Globe and Mail

A review of Ontario Proud’s history paints a web of links to the Tories. A significant amount of the cash it raised in 2018 was collected by professional fundraisers who, months before, courted donors for the Ontario Progressive Conservative Party.

Mr. Ballingall, too, is deeply enmeshed in conservative circles, both personally and financially: He worked in Ottawa for a former Conservative defence minister; his private company, Mobilize Media, was contracted in 2017 to help two federal Conservative leadership campaigns; and the Ontario PC Party paid Mobilize $67,800 for social-media services around that time as well.

These same issues of overlap between political advertisers and political parties swirl around union-backed, anti-Conservative groups as well. One of them, Engage Canada – which was founded by prominent former Liberal and New Democratic strategists – blanketed the airwaves with ads in the spring during the NBA playoffs – all of them broadcast, incidentally, before the federal disclosure period kicked in on June 30, allowing its funders and the exact cost of the ads to remain a secret. (Industry experts estimated that Engage’s prime time television ads, which portrayed Mr. Scheer as a pliable, bobblehead doll, would have cost between $45,000 and $75,000.) As of the publication of this story, Engage Canada had still not registered as a third-party advertiser with Elections Canada.

And it’s not just regulators who are concerned. Even one of the third-party advertisers agreed that this regulatory black hole is a problem.

Taylor Scollon, the co-founder of the progressive third-party political advertiser North99 pointed out that Canadian elections have disclosure rules, and limits, in order to restrict the amount of influence powerful and well-resourced organizations can have on public opinion. But those rules do not reflect the reality of campaigns that last 365 days a year, he said.

“If the campaign is every day – if we now have permanent campaigns – then we should apply the same reasoning and require disclosure during non-election periods,” Mr. Scollon said.

Back in 2016, however, when Mr. Essensa gave his public warning to Ontario lawmakers about what he saw on the horizon, Ontario Proud and North99 were not on anyone’s radar. Although Mr. Essensa did not single out a specific third party, he was likely referring to the group that paved the way for such players – an advocacy group that the Tories have long said unfairly targeted their leaders until they were compelled to fight back: The Working Families Coalition.

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Kingston, 1999: Police try to keep protesters away from Ontario Progressive Conservative leader Mike Harris's campaign bus, which had been leaving a breakfast meeting. Labour movement opposition to Mr. Harris's government helped create Canadian equivalents to the political action committees active in the United States.Jack Chiang/Kingston Whig-Standard/The Canadian Press

The birth of the Canadian-style political action committee was on the left of the political spectrum.

It was 1998, and Mike Harris, Ontario’s Progressive Conservative premier at the time, had effectively used wedge politics to create enemies of organized labour groups who he said were bankrupting the province at the expense of hard-working Ontario taxpayers. The Harris government had repealed labour laws, making it more difficult for trade unions to become certified.

So when the union leaders who represent electricians, pipefitters and iron workers and others arrived in Kingston for the annual meeting of the Building Trades Council – an umbrella organization of trade unions − they vowed to turn the tables. They passed a resolution to push back with their own form of messaging, one that would inform the public about what they say was the damage wrought, not by them, but by the Harris government.

At first they called it the Building Ontario Campaign, and it launched in time for the 1999 Ontario election. But they barely made a dent, and the Harris government was re-elected with a slightly smaller majority government. The council, however, saw room for improvement and impact − if only they could make their ads more effective.

“The big mistake that we made was that we did not hire professionals, pollsters and communications strategists and so on,” said Patrick Dillon, the Building Trades president at the time and one of the founders of Working Families.

They interviewed political operatives across the political spectrum and settled on two with close ties to the Liberals, Mr. Dillon said. Don Guy – who would go on to run the Ontario Liberal Party’s coming 2003 campaign – would conduct the group’s opinion polls through his company Pollara; Marcel Wieder – a well-known political consultant once profiled in this newspaper under the headline “The Dirty-Tricks Man” – was the strategist.

Other labour groups alienated by the Harris government, such as teachers and nurses, jumped on board. Thus was born the Working Families Coalition, an innocuous-sounding title designed to mask what its detractors argue is a dark mission – scuffing up the images of Progressive Conservative leaders.

That campaign made its debut on April 1, 2003, about six months before the next provincial election, and targeted Mr. Harris’s successor, then-premier Ernie Eves. Working Families produced a full-page newspaper ad, published in The Globe, prominently displaying a photograph of a smirking Mr. Eves in a tuxedo and bow tie, his hair slicked back. The bold text below the photo read: “Ernie Thinks He Can Fool You,” a play on the date April 1. The ad got a lot of attention, but Working Families was only getting started.

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In 2003, Working Families bought a full-page ad in The Globe and Mail targeting Ontario premier Ernie Eves.

Over the next three provincial elections, the group would repeatedly dip into its deep war chest, buy airtime and ratchet up the caricaturing of conservative leaders as heartless Bay Street puppets.

After electoral losses in 2003 and 2007, the Progressive Conservatives had had enough and the party formally asked Mr. Essensa to investigate what it alleged was co-ordination between Working Families and the Liberal Party.

One of the pieces of evidence they pointed to was the dual roles of Mr. Guy, who was the Liberal campaign director in 2003, 2007 and 2011, and whose firm, Pollara, was retained by Working Families.

The subsequent investigation, conducted with assistance from Bay Street firm Torys LLP, found that although Mr. Guy’s ties to the party and Working Families was “grounds for concern,” there was insufficient evidence that the Liberal Party was controlling the coalition, and therefore, there was no violation of the anti-collusion provisions.

Although that finding was Mr. Essensa’s to wear, he did not appear happy about it. His testimony in 2016 to the standing committee made it clear that he was frustrated with the outcome, and although he didn’t identify Working Families by name, he said the legal bar for proving collusion was too high.

“I will leave it to the lawyers to tell you how hard it is to prove there is direct evidence of this sort of control,” he said before legislators. But he said those who raise concerns about strategists playing for two teams – a political party and a third-party advertiser – have a point. Such close affiliation “undermines confidence in the electoral process. The public can plainly see that candidates and organizations that claim to be non-partisan are able to actively co-ordinate their advertising.”

As a last gasp, the Progressive Conservatives tried to get the courts to intervene and overturn Mr. Essensa’s ruling, but the case was dismissed at Divisional Court and the Ontario Court of Appeal. Working Families ran more ads during the 2014 campaign, which the PCs lost again, and there was no reason to believe anything would change.

But in a high-rise office building in downtown Toronto, there was a restless conservative operative, working for one of the country’s premier public affairs and crisis communications companies.

Jeff Ballingall had followed the well-worn path of a young conservative ideologue: as a teenager, he volunteered for the local Canadian Alliance candidate in his hometown of Sarnia, Ont., a working-class city of about 70,000 in the southwestern part of the province.

After graduating from the University of Western Ontario, he worked as a political staffer, first for Conservative defence minister Gordon O’Connor in Ottawa and, later, a right-leaning Toronto city councillor. He had a brief stint at the short-lived Sun News television network before finally landing where so many young, ambitious conservative strategists before him had found a home: Navigator Ltd., the public-relations company founded by well-known Tory spin master Jaime Watt.

But it was at Navigator where Mr. Ballingall decided to shake things up.

For years, he had been brainstorming about how a conservative third-party advertiser in Canada might work. When a friend had some success with an Alberta-centric Facebook page, Mr. Ballingall sought and obtained his blessing in early 2016 to launch an Ontario equivalent – calling it Ontario Proud.

As he fiddled with the page, he applied another lesson he learned at Navigator: Whenever Navigator was trying to disseminate a message on behalf of one of its corporate clients, those messages didn’t stick – especially when the message was coming directly from the corporation. Audiences were skeptical of a corporation advocating for itself.

“But if you can talk about it in a different way, and from a different messenger, they’re more receptive,” he said.

In August, 2016, he left Navigator and devoted himself full-time to his creation.

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An Ontario Proud post from April 6, 2016, targets Ms. Wynne over funding to autistic children.Facebook/Ontario Proud

At some point in 2016, then-Ontario premier Kathleen Wynne was being driven to an event when she pulled out her tablet to take the pulse of social media. That’s when, she says, she discovered a Facebook page that seemed to have some traction.

“It seemed like this bright, cheery thing,” she said in an interview. “Ontario Proud? I’m a proud Ontarian. What is this?”

“This” was going to make her re-election prospects even worse.

Ontario Proud had hit a mark that everyone in the eyeball-attraction business is striving for: engagement. Mr. Ballingall’s posts about Ontario roadside attractions and some of its famous citizens – Shania Twain, John Candy, the Friendly Giant − struck a chord. But most important, they were shared widely, which allowed Mr. Ballingall to collect all sorts of data about his followers and their interests. One of the first Ontario Proud posts to go viral was a photo of Webers, the burger joint north of Toronto in cottage country where diners eat in refurbished train cars. Like many of Mr. Ballingall’s posts, the Webers meme urged readers to spread the nostalgia: “Share if you know where this magical burger place is.” Eighty thousand people reposted the photo on their Facebook page, thereby introducing their friends to Ontario Proud.

But there was a whole other side to Ontario Proud.

Ontario Proud took a hard line on certain ideological issues, such as military intervention (“share if you believe Canada should still bomb ISIS”) and immigration policy (“criminals and terrorists will prey on our generosity”). But its hardest line was reserved for Ms. Wynne.

It referred to Ms. Wynne as a “clown,” a “scumbag” and “corrupt.” Just like Working Families spoofed Ernie Eves on April 1, Ontario Proud used the date to target Ms. Wynne and her minister of energy at the time, Glenn Thibeault, but with the insult dial cranked up a notch. A photo of the two Liberals was captioned: “Happy April – here are some fools.” On one occasion, which Mr. Ballingall says he now regrets, Ontario Proud went after Ms. Wynne’s appearance, comparing her spectacled look to that of the late Orville Redenbacher, the iconic popcorn maker: “What’s the worst part of grocery shopping in Ontario? Seeing the premier’s face in the snack aisle.”

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An April Fool's Day post targets Ms. Wynne and Glenn Thibeault, then the energy minister. Mr. Ballingall says he now regrets another ad comparing the premier to popcorn pitchman Orville Redenbacher.Facebook/Ontario Proud

In an interview earlier this year with Ms. Wynne at her office in the Ontario Legislature, where she now sits as a Liberal MPP after her government was handily defeated in the 2018 provincial election, she says she’s not willing to give too much credit to Mr. Ballingall for her downfall. Her party had governed for 15 years and voters were clearly ready for a change.

But where she will acknowledge Ontario Proud’s impact was on how voters perceived her. “I don’t think I realized that this guy was going to be as potent as he was,” she said. Throughout the campaign, she said she heard a familiar refrain from her candidates when they described a day of door knocking: empathy for the local candidate, but an unspecified dislike of Ms. Wynne. When the Liberals attempted to drill down on what it was about Ms. Wynne that turned them off, the answers were vague, she said.

“I think it was that Ontario Proud, and whatever other forces were out there, were successful at making me the lightning rod for whatever anger [voters] had,” she said.

That opinion is, perhaps, one of the only things that Mr. Ballingall and the former Liberal leader agree upon.

At a speaking event in April, convened by Toronto’s Empire Club, Mr. Ballingall boasted about how Ontario Proud made Ms. Wynne “socially unacceptable” to voters. And if people are offended by his language and name-calling, he said in an interview, they can point their finger in the direction of Working Families, one of the many motivators for creating his own right-wing, third-party advertiser.

Working Families is a common theme in any discussion with Mr. Ballingall about his brainchild. Asked to defend some of the insults Ontario Proud has hurled at Ms. Wynne, he pivots to the attacks endured by Progressive Conservative leaders for more than a decade by Working Families. He also revels in what he says is his underdog status – explaining that while Working Families can effortlessly turn to its deep pool of member-donated cash to fund its ads, he only relies on hustle, his knack for crafting concise, highly consumed content and his ability to persuade a disparate group of individuals and companies to support him financially.

But Mr. Ballingall is not quite as handicapped as he portrays himself. For one, he has had help from professional fundraisers who, up until 2017, worked directly for Ontario’s Progressive Conservative Party.

That year, the same year that Ms. Wynne’s government banned union and corporate donations to political parties, the Ontario PCs parted ways with two of the party’s top in-house fundraisers: Mariana Di Rezze and Sharon Flashford, both of whom have cultivated relationships with some of Ontario’s wealthiest citizens and amassed thick Rolodexes of potential donors.

Both women went on to raise money for Ontario Proud under the banner of their new fundraising company, RevGen Professional Fundraisers.

It was in 2018, around the same time Mr. Ballingall turned to RevGen, that he says Ontario Proud raised “big money.” Ontario Proud’s three largest donations were: $50,000 from Nashville Developments, which lists well-known builders Silvio DeGasperis and Jack Eisenberger as two of its officers and directors; $50,000 from Merit Ontario, an association of non-unionized contractors that has lobbied the provincial government to allow its members greater access to bid on public-sector projects; and $100,000 from Mattamy Homes, the colossal home builder whose billionaire founder, Peter Gilgan, has made headlines for his outsized philanthropy across the province.

All in all, during the six-month period that Ontario Proud is required to disclose donors, it raised $489,000. But this was not entirely the doing of RevGen, Mr. Ballingall says. “They helped,” he said. He also says he never co-ordinated with the fundraisers when they were directly employed by the PC fund and, what’s more, he didn’t even know them before they left the employment of the party.

Ms. Di Rezze and Ms. Flashford declined to respond to questions about how RevGen – which has been contracted to raise money for the PC Party – came to work for Ontario Proud. But, in a statement, they said that their company does not share information between clients. “All clients’ donor data is the exclusive property of the client and is not used for any other purpose.”

Mr. Ballingall had other money-making tools at his disposal. As a publisher of content that people like to read and share, Ontario Proud can also disseminate messages for businesses and industries – for a fee. In the media business, such advertisements are known as “sponsored content,” and are usually labelled as such to ensure readers don’t confuse an article that has been bought and paid for as a piece of journalism. Ontario Proud has published sponsored content, none of it labelled.

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An excerpt from a 2018 Ontario Proud video criticizing the Wynne Liberals' plans for home-care services for seniors.Facebook/Ontario Proud/Ontario Proud/Facebook

For example, in May, 2018, Ontario Proud posted a video titled: “Wynne’s Attack Dogs Get Special Deals.” The minute-and-a-half-long clip, which has been viewed nearly 90,000 times, criticized a Liberal plan to create a government-led agency to deliver home care to seniors.

It was not unusual for Ontario Proud to attack a big, expensive government program, but the message was actually paid for by Grosso McCarthy, a public affairs and strategy company that specializes in health-care policy. Ontario Proud charged the company $7,000 and disclosed it in its filings to Elections Ontario.

In an interview, Francesca Grosso, one of the principals of Grosso McCarthy, said that her company did not consider the transaction to be a donation in the typical sense − rather, it was a payment for the creation of the video.

Mr. Ballingall told her the production of the video would cost about $6,000, and that Ontario Proud would charge an additional $1,000 to post the content and boost the ad through Facebook. “He was adamant that the amount would need to be disclosed given the way the rules were written, and I appreciated his interest in transparency,” she said.

“I thought this was a bargain, given that the cost of media buys and production costs are usually through the roof,” she said.

As for who else has paid Mr. Ballingall to post tailored messages, he won’t specify. When asked about the number of pro-Canadian oil posts, he acknowledged that he has “received support from the Canadian energy industry.” Mr. Ballingall estimated that less than 1 per cent of Ontario Proud’s posts are sponsored content, and he said that the group would never post material that was not in keeping with its core principles.

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Mr. Ballingall would not disclose how much his company, Mobilize Media, had made from Ontario Proud.Mark Blinch/The Globe and Mail

Then there is the matter of how Mr. Ballingall, himself, gets paid.

On paper, Ontario Proud is a not-for-profit corporation. (When the group’s lawyer, Mr. O’Connor, was called to testify before the House of Commons ethics committee, he described Ontario Proud in his prepared remarks as “predominantly” non-profit. Asked to clarify this in an interview, he said Ontario Proud is strictly non-profit and explained, “I may have, frankly, misspoke.”)

But just because Ontario Proud is prohibited from turning a profit doesn’t mean its vendors are. And one of Ontario Proud’s frequently used vendors is Mobilize Media, Mr. Ballingall’s company.

Mr. Ballingall will not disclose how much Mobilize has made from Ontario Proud and public records only offer a glimpse of what Mobilize charges. When Ontario Proud was starting to peak in 2017, records show that the PC Party hired Mobilize for “advertising/communications/media” work. Mr. Ballingall was also hired by both Tony Clement and Lisa Raitt during the federal leadership race at respective price tags of $3,500 and $28,406.05.

When asked whether he used Ontario Proud’s wide audience to help those clients, Mr. Ballingall said that when he took those contracts, Ontario Proud was not yet registered with any regulators as a third-party advertiser. “Would we work on a campaign now? No.”

Mr. Ballingall has also leveraged his success into a job as the chief marketing officer of The Post Millennial, a digital news website with a distinct populist bent. Ontario Proud regularly disseminates Post Millennial stories through its Facebook and Twitter pages.

Throughout their interview with The Globe, Mr. Ballingall and Mr. O’Connor repeatedly stressed that Ontario Proud prides itself on its independence – and that, far from merely echoing the talking points of the PCs or federal Conservatives, it is pushing the parties in certain directions, too.

Recently, in a rare critique of the Ford government, Ontario Proud lived up to that assertion. On Twitter, Ontario Proud retweeted a Globe editorial that criticized the Ford government’s lottery system for granting licences to entrepreneurs interested in opening retail cannabis stores. “Another failure from the Ford government. Half-baked, timid policy doesn’t serve their public or political interests,” Ontario Proud wrote.

“We wouldn’t want to be directed by a political party, even if it was legal,” Mr. O’Connor said. “We don’t want to have that reputation.”

With reports from Susan Krashinsky Robertson

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