EYES ON THE BALL — Housing and affordability will be main topics at the Cabinet retreat that kicks off Jan. 21, but among the names expected to haunt the hallways: DONALD TRUMP. Prime Minister JUSTIN TRUDEAU made it clear this week he’s ready for the prospect that Trump could soon be running the White House for a second time following his Iowa momentum. And Trudeau made it clear where he stands on a scenario of a Trump round 2, after the first frantic time in office, when the two famously butted heads. — Are we ready?: “No,” said THOMAS JUNEAU, associate professor of public and international affairs at University of Ottawa. “Politically, I understand why he would say that, but Canada is not ready. Nobody can be ready because it would be so unpredictable.” — Clock is ticking: Just 291 days until the Nov. 5 election. And a lot of what Juneau says Ottawa could do that would potentially Trump-proof Canada from unexpected shocks to the system, like the last time around, are structural and would take years. Canada has neglected to “diversify our trade and security relationships and invest far more in security and defense capabilities.” — Strategic weak points: Trade market access and the USMCA coming up for renewal in July 2026. Canada’s lagging defense spending as a NATO country and the prospect of a Trump White House launching a tariff battle over that fact. Our heavy reliance on U.S. defense and security contributions to NATO, NORAD, and Five Eyes intelligence sharing and more. Retired Lt. Gen. ANDREW LESLIE, who was CHRYSTIA FREELAND’s parl. sec during the Trump years and frequently traveled south of the border to meet with U.S. governors, said now’s the time for the Liberals to get ready for what could be a period of “significant turmoil and sort of emotion-driven and political decisions originating in Washington.” “The current Liberal government is very good at making announcements, but really bad strategic planning,” he tells Playbook. “This is a strategic issue which involves planning, so I don't think much has been done yet.” — Behind-the-scenes plays: Former diplomat COLIN ROBERTSON says Canada is likely to be better prepared this time around since last time Trump’s first electoral win came as “such a shock.” But a lot of the key diplomatic prep work ahead of a presidential election ends up being nearly invisible. “It's basically getting to know who the potential players are going to be, and it may not be a player that goes in right away but a player who enters in a couple of years. It's a contact sport. It's retail politics. It's retail diplomacy.” When Barack Obama ran against Hillary Clinton in 2008, the leak of a Canadian diplomatic memo caused embarrassment in Ottawa — the kind of thing that can cut off access to a candidate’s campaign team. “Our embassy, KIRSTEN HILLMAN, and our various consuls general will all be already well engaged, the war room is already probably in place and feeding back information,” Robertson said. “The embassy is already actively reaching out to think tanks like the American Enterprise Institute, the Heritage Foundation,” which are preparing “the mandate for change” and can end up serving as kind of a “kindergarten for the new administration.” LOUISE BLAIS, a former consul general in Atlanta in 2016, says Canada appears not yet ready to face a Trump 2.0, but there's still time on the diplomatic front. “There is an effort being made now,” she tells Playbook. “The ambassador is traveling outside of Washington, D.C., a lot more than she did earlier on in her tenure.” Hillman talked to Playbook about that back in December. Former diplomat FRANK MCKENNA tells Playbook he’s not worried about prep for post-November, regardless of who ends up in office. “The people I talk to in Ottawa are well aware of what needs to be done,” he said. “They're engaged in preparation, certainly, the beginning of preparation for NAFTA negotiations is taking place and then there are a lot of cross-border discussions taking place now between various parties in the U.S. and Canada. I would say that people are seized with it.” | 
