Trump’s vexing Venezuela position

Republican Matt Van Epps won a closely watched special election in Tennessee last night, defeating Democrat Aftyn Behn. But Republicans writ large may still be wringing their hands as they look forward. Despite Van Epps’ relatively easy victory, the margin of victory — which drastically trailed President Donald Trump’s edge in the district last year — shows that Republicans still have work to do to find a message that lands on affordability. Playbook’s Jack Blanchard and White House Bureau Chief Dasha Burns break down what the results mean for the midterms and whether Trump can strike the right chord on cost-of-living issues.

President Donald Trump is holding his latest made-for-TV Cabinet meeting today, where all eyes will be on Pete Hegseth. The Defense secretary has captured headlines over the legality of airstrikes the U.S. conducted on the boats of alleged “narcoterrorists” around Venezuela — with a Washington Post report over the weekend raising more questions from Republicans and Democrats. Both Trump and Hegseth in recent days have voiced support for the action but distanced themselves from the report. Playbook’s Jack Blanchard and Pentagon reporter Paul McLeary unpack what to know, plus the latest on Ukraine peace talks.

The Trump administration pressure campaign against Venezuela and strikes against alleged drug-trafficking boats in the region are coming under increased scrutiny after reporting that caught the attention of bipartisan members of Congress. President Donald Trump offered cautious support for Defense Secretary Pete Hegseth’s involvement. It comes after Trump’s controversial decision to pardon former Honduran President Juan Orlando Hernandez, who was convicted in the U.S. of drug trafficking. Playbook’s Jack Blanchard and White House Bureau Chief Dasha Burns break down what to expect next, plus Trump’s next immigration crackdown.

A stunning transcript reportedly detailing Steve Witkoff’s private conversation with one of Russian President Vladimir Putin’s top aides reveals the approach that President Donald Trump’s administration is taking to end the war in Ukraine. The White House hasn’t denied the transcript’s validity, and the revelation comes as Trump’s plans to dispatch emissaries to meet with Putin next week. Playbook’s Jack Blanchard and diplomatic correspondent Felicia Schwartz walk through the stakes. Plus, the FBI opens investigations into six Democratic members of Congress who Trump is accusing of sedition.

President Donald Trump has dispatched Army Secretary Dan Driscoll to meet with Russian officials in Abu Dhabi over the Ukraine peace plan. The proposal is an updated version from the original 28-point plan, drafted by Steve Witkoff, which was criticized by many for favoring Russia. The new plan, which has been slimmed down, has garnered far more support in Kyiv and Ukrainian President Volodymyr Zelenskyy proclaimed that peace seems “doable” now. Playbook’s Jack Blanchard and Adam Wren break down what to know and what comes next.

Secretary of State Marco Rubio is back from Geneva, where he met with Ukrainian and European officials to negotiate a peace agreement to end the Russia-Ukraine war. Rubio said Sunday he was “very optimistic” about the progress thus far. President Donald Trump has set a Thursday deadline for Ukraine to accept a deal. Meanwhile, tensions with Venezuela are mounting as the U.S. amasses military resources in the region at a level not seen in decades. Playbook’s Jack Blanchard and diplomatic correspondent Felicia Schwartz discuss the stakes.

Dan Driscoll made history earlier this year when, at 38, he was sworn in as the youngest Army secretary in U.S. history. And he just made news again this week when he became the highest-level Trump administration official to visit Kyiv for the White House’s secret peace talks in effort to end Russia’s war on Ukraine. Driscoll joined high-level talks with Ukrainian officials, including President Volodymyr Zelenskyy, as news broke about a potential peace deal on the horizon. Driscoll is a veteran of the Iraq War, and as a result, has felt the effects of Pentagon decisions firsthand. He’s set out to reshape the U.S. Army and the Pentagon into an agile institution that can make better use of existing resources and channel the best practices of the private sector. “When you are creating defensive and offensive solutions, you have to think even 10 years out when the war really gets to its most catastrophic moment, ‘What are the very basic tools of warfare that can't be impacted by the enemy,” Driscoll said. In this week’s episode of The Conversation, Driscoll sits down with POLITICO’s Dasha Burns to delve into the future of warfare, his plans for reinvigorating the Army’s technology and the innovation spurred by conflict. “I think the best guess is if the United States entered a conflict with a peer in a couple of years, it would be a hybrid war where nearly every human being on the battlefield would be empowered and enabled with a digital tool,” Driscoll said. “I think we believe every infantryman in the United States Army will carry a drone with them into battle.” CNN "NewsNight" host Abby Phillip also joined Dasha to chat about her new book, “A Dream Deferred: Jesse Jackson and the Fight for Black Political Power,” Jackson’s influence on today’s political landscape and Phillip’s approach to her own roundtable show.

This afternoon, two politicians who embody diametrically opposite facets of New York City — President Donald Trump and NYC Mayor-elect Zohran Mamdani — will meet in Washington. Despite their myriad differences, both Trump and Mamdani are presently focused on the same issue: affordability. It’s a topic both men hinged their campaigns on. But will they be able to find any common ground? Playbook’s Adam Wren and New York Playbook co-author Nick Reisman walk through what they’re watching. Plus, exclusive reporting on the man at the center of Indiana’s redistricting resistance, and Barack Obama’s new role as mentor-in-chief.

Despite his continued insistence that cost-of-living concerns aren’t a problem, President Donald Trump is confronting subpar stats on the U.S. economy, as evidenced in the data and lived reality for Americans. The September jobs report that was delayed due to the government shutdown is expected to arrive today as fresh Fox News polling shows that more than three quarters of Americans view the economy unfavorably. Trump — and 2026 candidates up and down the ballot on both sides of the aisle — are reckoning with a sour economic state. Playbook’s Jack Blanchard and White House Bureau Chief Dasha Burns break it all down.

There appears to be some progress toward an end to the Russia-Ukraine war after months of start-and-stop talks between President Donald Trump and top-level negotiators. Army Secretary Dan Driscoll is reportedly traveling to Ukraine today with two high-ranking military officials for urgent talks with Ukrainian President Volodymyr Zelenskyy, armed with the early stages of a plan to bring the conflict to a resolution. Playbook’s Jack Blanchard and White House Bureau Chief Dasha Burns break down what we know, and what to expect next.