June 27, 2025: The megabill’s moment of truth

While the GOP megabill continues to be the main event in Washington, President Donald Trump heads to Florida and the latest hotspot in his immigration crusade: “Alligator Alcatraz.” That’s the moniker of a new detention camp deep in the Florida swamplands that will house undocumented immigrants. It’s not just a facility, of course: It’s an attempt to control the narrative around immigration, promulgate fears among would-be migrants and ultimately focus attention on an issue Democrats would rather not discuss. POLITICO White House reporter Myah Ward and Playbook author Jack Blanchard discuss.

It’s crunch time on Capitol Hill as the clock winds down for the sweeping Republican-backed reconciliation bill ahead of President Donald Trump’s self-imposed July 4 deadline. At stake is the crux of his legislative agenda, with massive real-world implications for millions of Americans on topics ranging from health coverage to taxes to food assistance for the poor. With Democrats eager to hold Republicans’ feet to the fire, will the GOP stick together, or are the slowly developing fissure lines enough to crack apart their legislative majorities? Chief Playbook correspondent Dasha Burns and author Jack Blanchard talk through the angles. Plus, the fallout from the U.S. attack on Iran continues, and an appeals court in Louisiana will consider Trump’s use of the Alien Enemies Act in his immigration enforcement.

President Donald Trump firmly believes the GOP’s megabill can pass through Congress and land on his desk by July 4. But with just one week to go before that self-imposed deadline, the sweeping legislation faces a congressional obstacle course, with Republicans across Capitol Hill fighting over facets from Medicaid cuts to government spending to federal land sales. POLITICO Congress reporter Jordain Carney joins Playbook contributing author Adam Wren to break down everything the state of play and where things go from here.

Freshly back from the NATO Summit, President Donald Trump’s attention is now focused squarely on one thing: selling the Iran strike as an unmitigated success — regardless of what intelligence assessments say. Today the administration will focus on trying to shift the narrative — casting questions about the efficacy of the strikes as a slap in the face of American military pilots, and blaming Congress for the leaked intelligence reports that contradict Trump’s claims. POLITICO White House reporter Megan Messerly joins Playbook author Jack Blanchard to walk through what to watch. Plus, the Democratic Party is only beginning to reckon with outsider candidate Zohran Mamdani’s primary election upset in NYC.

Two stories from opposite sides of the globe have huge political implications today. First, in New York City, outsider candidate Zohran Mamdani pulled off a historic upset, defeating former Gov. Andrew Cuomo in the Democratic primary for mayor. The seismic victory is sending shockwaves throughout American politics, with center-left Democrats gritting their teeth, progressives in a triumphant mood and Republicans lapping it all up. Across the Atlantic Ocean, President Donald Trump is at the NATO Summit at The Hague today, where he’s expected to address the ongoing fallout from the U.S. strike on Iran and the fragile ceasefire between it and Israel. POLITICO White House reporter Megan Messerly joins Playbook author Jack Blanchard to unpack all that and more.

President Donald Trump heads to the Netherlands today for the 2025 NATO Summit. The Iran-Israel conflict was already set to be a major focus. But Trump’s announcement Monday night of a ceasefire between the countries has reshaped the conversation altogether. Will the summit be an opportunity for Trump to flex on the global stage, or will he be received by a more tepid crowd? POLITICO White House reporter Megan Messerly joins Playbook author Jack Blanchard to discuss. Plus, a big day for hearings on Capitol Hill, and Democrats in New York City head to the polls to pick a mayoral nominee.

On Saturday night, U.S. forces bombed three Iranian nuclear facilities in what the Pentagon termed “Operation Midnight Hammer.” The consequences, which will likely be far-reaching, are only beginning to come into view. Does President Donald Trump want regime change in Iran? How would he square that pursuit with his America First pledges? What will it mean for nuclear talks? What sort of reprisals should we expect from Iran? Will Congress assert its war powers authority? And what does the world look like in the aftermath of the attacks? POLITICO White House reporter Megan Messerly joins Playbook author Jack Blanchard to unpack it all.

One story continues to dominate the conversation in Washington: the possibility of a U.S. strike in Iran. But even as the commentariat focuses on its potential geopolitical implications, its potential implications for American politics are no less real. President Donald Trump’s MAGA base is split over what to do. Does Trump risk hemorrhaging support if he orders a strike? Or is the whole idea of a GOP civil war over Iran overhyped? Playbook contributing author Adam Wren joins editor Zack Stanton to talk through his reporting and discuss what it all means for the conflict at hand and the future of MAGA.

With the U.S. on the cusp of potentially joining Israel’s fight against Iran, foreign policy experts in Washington are scrambling to game out the various scenarios. And as POLITICO senior foreign affairs correspondent and Compass columnist Nahal Toosi tells Playbook author Jack Blanchard, the options available to Trump and the possible outcomes from them aren’t simply black and white; they exist along a spectrum ranging from arming Israel for a single, targeted strike on an Iranian nuclear facility, to a more sweeping and wide-scale involvement. In the balance: the security of the Middle East, the political viability of Trump’s MAGA coalition and the futures of millions of everyday people in Iran. Nahal talks us through her reporting and the stakes.

President Donald Trump is unexpectedly back in Washington today, cutting his G7 trip short amid a spiraling situation with Iran. Yesterday, Trump made an ominous Truth Social post suggesting “everyone should immediately evacuate Tehran” — words that immediately provoked a fiery response from some of his usual supporters, who see the threat of such foreign interventionism as a betrayal of his “America first” ethos. Now, he faces one of the biggest dilemmas of his presidency: Should the U.S. back Israel in attacking Iran? And if so, to what extent? The implications are enormous — for the U.S., for the world and for Trump’s political project. Chief Playbook correspondent Dasha Burns and author Jack Blanchard talk it all, what they’re hearing and what to expect in the days ahead.