POLITICO Playbook Daily Briefing

A high-stakes election in Wisconsin is shaping up to be the first big test of Trump's new era, drawing over $100 million in spending. Influential figures like Elon Musk are backing this state's Supreme Court race, which could impact reproductive rights and political power. Meanwhile, voters in Florida will head to the polls for key special elections, with Democrats aiming to flip important seats. The discussions highlight the significance of voter turnout ahead of the midterms and how upcoming legislative maneuvers could affect Trump's agenda.

The podcast dives into the withdrawal of Elise Stefanik's UN nomination, unveiling its implications for Trump's agenda and Republican unity. As Stefanik shifts focus back to the House, the dynamics among congressional Republicans are analyzed. Meanwhile, Vice President JD Vance prepares for a significant trip to Greenland to address local issues. The discussion also touches on the competitive special elections in Florida, highlighting unexpected Democratic fundraising successes that may signal a shift in voter sentiment.

Maggie Miller, a POLITICO cybersecurity reporter, dives deep into the Signalgate controversy that’s capturing Washington's attention. She discusses why this scandal, stemming from a breach of confidential discussions, continues to resonate politically. The fallout has led to a blame game within the Trump administration, raising questions about the handling of sensitive communications. The episode also scrutinizes the risks of using commercial apps, like Signal, for government discourse, hinting at potential changes in communication policies.

In the wake of 'Signalgate', the White House faces turbulence as key figures navigate a crisis sparked by a major national security leak. National Security Advisor Mike Waltz is under scrutiny, with whispers about his future among the president's inner circle. The fallout reveals emotional reactions from reporters and a candid admission from the president about past mistakes. Confusion reigns among senior staff as inconsistent messaging raises questions about the administration's effectiveness and leadership moving forward.

A leaked group chat among top national security officials reveals sensitive war plans, leading to chaos in the Trump administration. The accidental inclusion of a journalist raises serious protocol breaches and national security concerns. Internal tensions come to light regarding U.S. military strategy and foreign alliances. Officials openly discuss classified topics over an unencrypted messaging app, sparking debates about security and communication practices. As Congress prepares for a crucial hearing, the implications of these revelations extend beyond borders.

Jordain Carney, a Congress reporter with a keen insight into political dynamics, joins to discuss the high-stakes race for a budget bill as Congress reconvenes. They dive into the visible fractures within the Republican Party, contrasting strategies between the House and Senate. Carney highlights the intense negotiations ahead, focusing on budget cuts and tax disagreements. Listeners will gain a fresh perspective on how these legislative pressures are shaped by Trump's leadership and the unique challenges of reaching a consensus in the tight timeframe.

The podcast dives into the Democrats' attempt to leverage Elon Musk as a campaign tool in the upcoming Wisconsin Supreme Court race. It questions whether this strategy will resonate with voters or leave the party floundering. Discussions also highlight Senator Bernie Sanders and Representative Alexandria Ocasio-Cortez's grassroots efforts against the establishment. With critical issues like abortion rights energizing voters, the podcast examines how influential figures are reshaping electoral dynamics in today's political landscape.

President Donald Trump’s multi-front battle on education is in full swing. Today, he’s expected to sign an executive order effectively dismantling the Department of Education; Columbia University faces a deadline to respond to the administration’s demands or else lose $400 million in funding; Penn finds itself under scrutiny as the administration takes issue with its policy on transgender student athletes; and Dartmouth staffs up as it seeks to remain out of the line of fire. POLITICO’s West Wing Playbook author and White House reporter Irie Sentner joins Playbook deputy editor Zack Stanton to discuss.

President Donald Trump is no stranger to pushing the limits. And since reentering the Oval Office, he’s put significant energy into pushing the limits of the law — testing the courts and the legal system in ways rarely before seen in this country. What’s behind that effort, and where does it go from here? Senior legal correspondent Josh Gerstein joins Playbook author and managing editor Jack Blanchard to discuss.

Today, President Donald Trump will talk with Russian President Vladimir Putin about a potential ceasefire between Russia and Ukraine. Trump, who told reporters over the weekend that significant progress has already been made in peace negotiations, is expected to make certain concessions for a successful deal. Can the two leaders come up with a plan to end the war — or get close to it? And will that plan sacrifice Ukraine’s own goals for the sake of a deal, whatever the costs? POLITICO national security reporter Eric Bazail-Eimil joins host Steven Overly to talk through what he’s watching. Plus, recent deportation decisions by the Trump administration call into question the limits of the president’s power. All that, and the rest of the news you need to know today.