May 29, 2025: Trump vs. the courts — again

Yesterday in Colorado, a man shouted “Free Palestine” as he attacked a group of elderly demonstrators who had gathered to peacefully advocate for the release of Israeli hostages in Gaza. The episode is at once the nation’s latest paroxysm of antisemitic violence and the newest flashpoint in the debate about immigration: the alleged assailant was reportedly in the country illegally, having overstayed a visa. Chief Playbook correspondent Dasha Burns and author and managing editor Jack Blanchard join unpack it all. That, plus a new wave of Ukrainian strikes hammer deep in Russian territory.

Listen to the first episode of Politico’s new podcast, The Conversation with Dasha Burns. Dr. Mehmet Oz, former TV host and Pennsylvania Senate candidate, is one of America’s most famous physicians. Now he’s running the Centers for Medicare and Medicaid Services, which means he’s in charge of programs that provide health care for about half of all Americans. He sits down with White House Bureau Chief Dasha Burns to discuss potential Medicaid cuts, his big plans to lower drug pricing, why he’s fielding early morning phone calls from President Trump, and his advice to patients to “be curious” about their health.  Plus, Burns is joined by senior political columnist and politics bureau chief Jonathan Martin to discuss his juicy column about the Ohio governor’s race featuring Elon Musk, Vivek Ramaswamy and former Ohio State football coach Jim Tressel. And senior legal affairs reporter Kyle Cheney joins to discuss the showdown between Trump and the courts over his “Liberation Day” tariffs.

It’s a swing state with an open U.S. Senate seat, several competitive House races, an open gubernatorial seat — oh, and a potential leading 2028 candidate serving as governor. You may call it a political wonk’s dream; we call it Michigan. This week, as the battleground state’s political stars descended on idyllic Mackinac Island, the trends that will likely define 2026 across the nation came into full view. Live from the Mackinac Policy Conference, Playbook contributing author Adam Wren and supervising editor Zack Stanton talk through what they learned about the direction the campaign is heading. That, and President Donald Trump goes to Pennsylvania to trumpet the new U.S. Steel deal, while some leading Democrats head to South Carolina for a trial run of potential 2028 campaigns.

President Donald Trump’s tariff agenda has largely relied on one central claim: that America faces a national emergency that justifies the president taking extraordinary measures. Yesterday, a federal court blew a hole in that rationale in a ruling striking down his tariffs on dozens of U.S. trading partners while teeing up yet another looming Supreme Court showdown. On issue after issue, the legal system has proven to be the one reliable restraint on Trump’s policy ambitions. And on issue after issue, the administration is eager to go to war against the judiciary. Where do those battles go from here? Chief Playbook correspondent Dasha Burns joins managing editor and author Jack Blanchard to map it out. That, plus Elon Musk’s DOGE days are over.

Even as President Donald Trump himself has a (relatively) quiet couple days, the gears of his administration continue to turn, and the pairing of his political and personal interests continues, brazenly and in the public. Today, Vice President JD Vance will deliver the keynote address at the Bitcoin 2025 Conference in Las Vegas. A few hours later, Eric and Donald Trump Jr. will speak at the same event, which comes just one day after Trump’s media company announced it intends to raise billions to stockpile Bitcoin for its corporate coffers. Chief Playbook correspondent Dasha Burns joins managing editor and author Jack Blanchard to talk through that, the president’s latest social media output, some notable 2026 maneuvering and an exciting announcement from Dasha.

The biggest story in Washington today isn’t really in Washington; it’s about how Washington is affecting pretty much every place else. With Congress out on Memorial Day recess, the focus in D.C. today is all international — from Iran nuclear talks to trade negotiations with the European Union to the war in Ukraine to Gaza to King Charles’ visit to Canada. And there is a fairly consistent through line connecting it all, chief Playbook correspondent Dasha Burns tells managing editor and author Jack Blanchard: Trump’s strategy of first destabilizing an institution or status quo and then seeking to reshape it. Where will it prove successful, and where will it come up short? We may get a few signs this week. That, and the rest of the news you need to know as the week revs back.

Revenge, the saying goes, is a dish best served cold. And this week, the Trump administration is serving up a veritable buffet. Whether blocking Harvard University from enrolling international students, launching a Federal Trade Commission investigation into Media Matters, or using the long arm of the DOJ to prosecute Democratic elected officials, President Donald Trump’s government is mounting a show of force against its perceived opponents. But how does this revenge tour align with what MAGA voters expected from Trump 2.0? Playbook supervising editor Zack Stanton breaks it down with contributing author Adam Wren. Plus, swing-district House Republicans are already seeing the political liabilities that come with voting for the sprawling reconciliation package, and a stunned Washington mourns two Israeli embassy staffers murdered in downtown D.C.

Tonight, Donald Trump goes where no president has gone before: to an invite-only dinner for investors in a cryptocurrency bearing his name. The unprecedented event is the latest in a pile of entanglements that raise serious questions about palm-greasing and profiteering — from deals for Trump-branded golf courses to the $400 million jet Qatar gifted to the administration for use as Air Force One. Playbook managing editor and author Jack Blanchard digs into it all with contributing author Adam Wren. Plus, HHS Secretary Robert F. Kennedy Jr. releases its first MAHA Commission report, and the House GOP’s mammoth megabill takes a big step forward.

Former President Joe Biden is trying to lay low. But with the conversation in Washington dominated by the fallout from his cancer diagnosis and the continuing revelations from Jake Tapper and Alex Thompson’s book “Original Sin,” his every move is fodder for more discussion — welcome or not. Playbook contributing author Adam Wren joins managing editor and author Jack Blanchard to dig into it all. Meanwhile, the GOP megabill continues to progress through the House, as GOP leadership eyes the legislative endgame. And South African President Cyril Ramaphosa arrives at the White House to try and defuse Trump’s furor over the alleged mistreatment of Afrikaner farmers.

The year’s most anticipated book in Washington has finally arrived: Jake Tapper and Alex Thompson’s “Original Sin” dropped overnight, just as Joe Biden’s physical and cognitive health as president is the topic dominating the D.C. discourse. And the din of that conversation is likely to only grow louder. Partly, that’s because the Biden story isn’t going away. But it’s also because Republicans are eager to keep the focus there rather than the politically risky proposed cuts to Medicaid that have now taken center stage in the debate over the House GOP’s Big Beautiful Bill. President Donald Trump heads to Capitol Hill this morning to try and win over Republican holdouts. Playbook contributing author Adam Wren joins managing editor and author Jack Blanchard to unpack it all.