Canada’s Premiers Hire $85K/Month Lobbying Firm After Meeting Donald Trump Jr.
Canada’s provincial and territorial leaders hired a Washington lobbying firm for $85,000 a month. The decision followed a meeting between Yukon Premier Ranj Pillai and Donald Trump Jr. The firm, Checkmate Government Relations LLC, helped the premiers secure meetings with U.S. officials amid rising trade tensions.

How the Lobbying Deal Began
The premiers met in Mississauga, Ontario, last year to discuss trade issues. They reacted to Chrystia Freeland’s unexpected resignation from the federal cabinet. The group included three former Washington ambassadors who saw Freeland’s departure as a crisis. They believed it would change Canada’s ability to manage U.S. relations.
Pillai reached out to Donald Trump Jr., whom he had met before. He attended a gathering in North Carolina, where he met Charles F. McDowell IV. McDowell, a friend of Trump Jr., is a partner at Checkmate Government Relations. Pillai introduced McDowell to Ontario Premier Doug Ford, chair of the Council of the Federation. Ford was considering options to strengthen U.S. connections.
The Lobbying Contract
Checkmate Government Relations was hired to assist with U.S. outreach. The contract, available under the U.S. Foreign Agent Registration Act, outlines the firm’s role. It makes no guarantees about the success of negotiations but commits to helping the premiers navigate Washington politics.
The firm has ties to the Trump administration. One of its employees, Chris LaCivita Jr., is the son of a Trump campaign co-chair. The company recently moved to Washington from North Carolina. Addison McDowell, brother of Charles McDowell, became a U.S. congressman this year.
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U.S.-Canada Tensions and the Lobbying Effort
The lobbying effort comes amid rising tensions over tariffs. President Donald Trump has cited fentanyl trafficking as a reason for imposing tariffs on Canadian goods. This issue is personal for the McDowell family. Luke McDowell, another brother, died from fentanyl poisoning in 2016. Last week, Addison McDowell spoke in Congress about fentanyl, supporting a bill to combat the crisis.
The premiers traveled to Washington to argue against tariffs. They secured meetings with senior White House officials but did not meet Trump. Deputy Chief of Staff for Legislative Affairs James Blair tweeted that the meeting was “pleasant” but sarcastically added, “We never agreed that Canada would not be the 51st state.”
Fallout and Reactions
Trump later mocked Canada’s military and economy. He suggested that Canada was “a serious contender” to become a U.S. state. Pillai dismissed these comments and remained focused on trade.
“[Let’s] just be laser-focused on what we have to do. Like, there’s a border issue. We’ve responded,” Pillai said. “Donald Trump’s not going to own the Arctic and he’s not going to own Canada. But he will own inflation if these tariffs come in.”
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British Columbia Premier David Eby acknowledged that Checkmate Government Relations helped secure meetings.
“This was a meeting on short notice with senior decision-makers,” Eby said. “I was glad for the conversation. I’m glad they made the time.”
The effectiveness of the lobbying effort remains unclear. The premiers aim to prevent tariffs that could impact Canadian industries. Their new lobbying firm will play a key role in ongoing negotiations.
More…
- https://weeklyvoice.com/canadian-premiers-hire-u-s-lobbying-firm-after-chance-meeting-with-donald-trump-jr
- https://www.cbc.ca/news/world/premiers-washington-lobbyist-checkmate-1.7458770
- https://www.reddit.com/r/CanadaPolitics/comments/1ip1l8m/how_a_meeting_with_donald_trump_jr_led_canadas
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