Darryl Dyck/CP PM Trudeau in Vancouver on Nov. 1, 2018.

OTTAWA — A conservative political advocacy group that was instrumental in taking down the Liberals in Ontario is going national, aiming to do to Justin Trudeau what it did to Kathleen Wynne. But the arrival of Ontario Proud on the federal scene renews questions about when political advocacy crosses the line into collusion with a political party, enabling the party to raise and spend more money than legally allowed and, in the process, undoing decades of effort to neutralize the influence of big money on Canadian elections. Ontario Proud was founded by Jeff Ballingall, a digitally savvy former Harper-era Conservative staffer and erstwhile employee of the short-lived Sun News Network.

Andrew Vaughan/CP PM Trudeau and former Ontario Premier Kathleen Wynne at the federal Liberal national convention in Halifax on Apr. 20, 2018.

It unabashedly promoted Doug Ford's Progressive Conservatives in last spring's Ontario election, using social media to create viral videos and memes that mercilessly mocked Wynne before shifting to attack the NDP once polls showed the premier's party cratering. In a "victory update" to supporters in June, Ballingall boasted that Ontario Proud's Facebook content was viewed almost 67 million times — more interactions than the Facebook pages of the three main parties, their leaders, the unions and all other political advocacy groups "combined!" The group ran "an aggressive voter contact campaign" to identify Progressive Conservative supporters and mobilize them to vote, by way of one million-plus text messages and 2.5 million phone calls. It hired "street teams" to hand out 15,000 brochures and mailed out 600 "unplug Wynne" lawn signs. Ontario Proud "drove the narrative" of the campaign, Ballingall boasted in the update. "We delivered on our goals: a defeat of the Kathleen Wynne-led Liberals and a 'sunlight' campaign that exposed the NDP's extreme candidates and agenda, ultimately helping to deliver a majority government for the Progressive Conservatives." 'Ontario Proud is building a war chest to take down Justin Trudeau' The group has accomplished all this as a registered third party — legal parlance for a political advocacy group — that bills itself as a non-partisan, not-for-profit, grassroots organization. And it's now gearing up to the do the same for Andrew Scheer's Conservatives in next fall's federal election. "Just like we did with Kathleen Wynne, Ontario Proud is building a war chest to take down Justin Trudeau," the group announced in a recent fundraising email. The Liberal party is bracing for the onslaught, warning in its own fundraising plea last week that Ontario Proud, "founded and directed by alumni of Stephen Harper's government," will use tactics known for "lowering the bar for political discourse." We delivered on our goals: a defeat of the Kathleen Wynne-led Liberals and a 'sunlight' campaign that exposed the NDP's extreme candidates and agenda, ultimately helping to deliver a majority government for the Progressive Conservatives.Jeff Ballingall, Ontario Proud Ballingall says Ontario Proud's precise plans for the Trudeau takedown will depend on the rules for third parties, which are in flux at the moment. Currently under the Canada Elections Act, third parties that spend more than $500 during a federal election must register with Elections Canada. They can spend just over $200,000 on advertising during a campaign but as much as they want before its official start. Whereas political parties are banned from accepting donations from corporations or unions and face a strict $1,575-cap on individual donations, third parties face no restrictions on donors or the size of their contributions. The act expressly forbids colluding with political parties to circumvent the spending limits imposed on parties in a bid to level the monetary playing field. We dove in to the 'nasty' messaging Canadians stand to encounter during election 2019. Story continues after the latest episode of Backbenchers.