One thing Donald Trump loves to say is that he knows how to make a deal. And even for our allies, sometimes the “Art of the Deal” can feel like a shakedown. Ask NATO about that, and you’ll get some nods. But lately, Canada is the ally that’s been caught in Trump’s line of sight.

The president-elect has been trolling Prime Minister Justin Trudeau on social media, calling him the “governor” of America’s “51st state,” and threatening to impose a 25 percent tariff on Canadian imports if they don’t step up their game on border security.

On this episode of Playbook Deep Dive, Canada’s ambassador to the U.S., Kirsten Hillman, joins Playbook co-author Eugene Daniels to discuss how Justin Trudeau’s embattled government is rolling with Trump’s punches; enduring their own political crisis and making inroads with Trump world.

Eugene Daniels is a Playbook co-author for POLITICO.

Kirsten Hillman is the Canadian ambassador to the U.S.

Kara Tabor is a producer for POLITICO audio. 

Alex Keeney is a senior producer for POLITICO audio.

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Donald Trump’s Washington is going to be packed with heavyweights from big business such as Elon Musk, Scott Bessent and Howard Lutnick. But the U.S. Chamber of Commerce, which represents traditional business interests in D.C., has recently found itself estranged from its longtime allies in the Republican Party. On this episode of Playbook Deep Dive, the Chamber’s top lobbyist, former Rep. Rodney Davis, joins Playbook co-author Rachael Bade to discuss how the Chamber is winning back its swagger with the GOP and how they plan to interface with President-elect Trump.

Rachael Bade is a Playbook co-author for POLITICO.

Rodney Davis is the Head of Government Affairs at the U.S. Chamber of Commerce.

Kara Tabor is a producer for POLITICO audio. 

Alex Keeney is a senior producer for POLITICO audio.

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Generational change. It’s been a hot topic for Democrats ever since Joe Biden announced he’d run for a second term, and it's been picking up steam this past week as House Democrats pushed aside aging ranking members on key committees in order to make room for some younger leaders. In this episode, Playbook co-author Eugene Daniels speaks with Rep. Jared Huffman, who is challenging for the top Democratic slot on the House Natural Resources Committee, about what and who is behind this generational rebellion.

Eugene Daniels is a Playbook co-author for POLITICO.

Jared Huffman is the representative for California's 2nd district.

Kara Tabor is a producer for POLITICO audio. 

Alex Keeney is a senior producer for POLITICO audio.

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Sen. Kevin Cramer (R-N.D.) weighs in on President-elect Trump’s cabinet picks, the news of former Rep. Matt Gaetz’s withdrawal from attorney general consideration and his takes on some of the incoming president's most controversial ideas.

Rachael Bade is a Playbook co-author for POLITICO.

Kevin Cramer is the junior senator from North Dakota.

Kara Tabor is a producer for POLITICO audio. 

Alex Keeney is a senior producer for POLITICO audio.

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Sen. Sherrod Brown (D-Ohio) opens up for the first time about his recent defeat, and what he thinks his experiences holding a senate seat in reliably red Ohio since 2006 can teach fellow Democrats attempting to redefine the party’s brand.

Eugene Daniels is a Playbook co-author for POLITICO.

Sherrod Brown is the senior senator from Ohio.

Kara Tabor is a producer for POLITICO audio. 

Alex Keeney is a senior producer for POLITICO audio.

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Donald Trump is coming back to the White House. On this episode of Deep Dive, POLITICO’s top Trump-ologist, Meridith McGraw, and Playbook editor Mike DeBonis join host Rachael Bade to discuss how the next Trump presidency will defy our expectations. 

Included in this discussion: 

Who will be in Trump’s cabinet; who will lead the GOP on the Hill and can Trump really be sure that they’ll cooperate with him? On the Democratic side — how will they respond to their crushing defeat? And will they resist Trump’s every move as doggedly as they did during his first administration?

Rachael Bade is a Playbook co-author for POLITICO.

Meridith McGraw is a national political correspondent for POLITICO.

Mike DeBonis is the editor of Playbook for POLITICO.

Kara Tabor is a producer for POLITICO audio. 

Alex Keeney is a senior producer for POLITICO audio.

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Top election forecasters Lakshya Jain (Split Ticket) and Logan Phillips (Race to the White House) join Playbook co-author Eugene Daniels to give their key insights and predictions for Tuesday. They discuss how to analyze early voting returns, who the remaining swing voters are, and why polls are more useful than most people give them credit for. Stay until the end, where they each share what one race that will be called early on Election Night that will signal to them who the next president is going to be.

Eugene Daniels is a Playbook co-author for POLITICO.

Lakshya Jain is CEO and co-founder of Split Ticket.

Logan Phillips is founder of Race to the White House.

Kara Tabor is a producer for POLITICO audio. 

Alex Keeney is a senior producer for POLITICO audio.

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Election Day is less than two weeks away. And Donald Trump has been employing an innovative strategy to keep Democrats’ — and an increasingly large number of Republicans’ — doubts about his fitness for office at bay. The former president has been burnishing his image on a nontraditional media spread of podcasts, golf outings, and shifts working at McDonald's. 

To understand Trump’s own thinking about the campaign, including the risks of this unorthodox strategy and the most recent indictments of his character, Playbook co-author Rachael Bade sat down with one of his most trusted advisers: Jason Miller.

Miller and Trump have a long history together. He’s worked on each of Trump’s campaigns since 2016, in roles ranging from comms guru to senior strategist, and he isn’t afraid to elaborate on the campaign’s strategy or defend Trump’s most controversial comments.

Rachael Bade is a Playbook co-author for POLITICO.

Jason Miller is a senior adviser to President Donald Trump.

Kara Tabor is a producer for POLITICO audio. 

Alex Keeney is a senior producer for POLITICO audio.

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Trump, Harris, and the vast network of campaigns, Super PACs, and down ballot candidates operating alongside them are now on pace to spend $1 billion before election day in Pennsylvania. For the time being, it is the center of the political universe. On this episode of Deep Dive, Playbook co-author Eugene Daniels is joined by two local experts on the race: Philadelphia City Councilmember Isaiah Thomas, who is the Chair of Black Men for Harris Pennsylvania; and Charlie Gerow, a Trump surrogate, Republican consultant in Harrisburg, and former candidate for governor.

Eugene Daniels is a Playbook co-author for POLITICO.

Isaiah Thomas is a Philadelphia City Councilmember At-Large and Majority Whip.

Charlie Gerow is the CEO of Quantum Communications and a Republican consultant.

Kara Tabor is a producer for POLITICO audio. 

Alex Keeney is a senior producer for POLITICO audio.

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The 2024 election. It’s a contest between Kamala Harris and Donald Trump. But increasingly, it also looks like it’s girls versus boys. 

Playbook’s Rachael Bade caught up with Sarah Longwell, Executive Director of Republican Voters Against Trump, Publisher of The Bulwark, and Host of "The Focus Group" Podcast, to learn what is driving a record-setting gender gap this election cycle. Longwell has conducted hundreds of focus groups and knows intimately how voters, in their own words, are processing Harris and Trump’s candidacies, and what issues and ideas will determine who they vote for.

Rachael Bade is a Playbook co-author for POLITICO.

Sarah Longwell is the CEO of Longwell Partners, Publisher of The Bulwark, and host of "The Focus Group" podcast

Kara Tabor is a producer for POLITICO audio. 

Alex Keeney is a senior producer for POLITICO audio.

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