The Supreme Court closes its term with a major win for Donald Trump, issuing high-stakes rulings on birthright citizenship, LGBTQ+ content in schools, and more. Senior Writer at Slate Mark Joseph Stern and Andrea Flores, VP for immigration policy and campaigns at FWD.US, join The Weeknight to break down what the decisions mean for America. Plus, Senior Fellow at the Council on Foreign Relations Max Boot reacts to the Senate blocking a war powers resolution that would have limited President Trump’s ability to attack Iran without Congressional approval.

Republicans are scrambling after learning their proposed cuts to Medicaid, which would offset trillions in tax breaks, violate Senate rules. Reps. Ayanna Pressley and Sydney Kamlager-Dove join The Weeknight to break down what this could mean for Americans. Plus, Senator Chris Van Hollen discusses what he sees as a dangerous lack of transparency from the Trump administration in the Middle East. And Congresswoman LaMonica McIver is vowing to fight the Trump DOJ for as long as it takes.

Senate Democrats grilled former Trump lawyer Emil Bove about whistleblower claims that he suggested Justice Department lawyers ignore court orders on deportations. Sen. Peter Welch, who questioned Bove today, joins The Weeknight. Plus, former Under Secretary of State Rick Stengel and New Yorker staff writer Susan Glasser discuss the crisis of credibility facing Trump’s foreign policy in the Middle East. And what the New York Democratic Mayoral primary results mean for Democratic strategy headed into the 2026 midterm elections.

With lawmakers on both sides questioning the limits of Trump’s war powers, Rep. Joaquin Castro of the House Intelligence Committee joins The Weeknight to discuss breaking news that the U.S. strikes in Iran were not as effective as the President claimed. Plus: Fresh off his election as the new top Democrat on the House Oversight Committee, Rep. Robert Garcia joins to discuss his plans to confront Trump and lead the charge on accountability.

Former CIA Director John Brennan joins The Weeknight to break down the latest developments in the U.S. conflict with Iran, and what it means for America’s role in the Middle East. Plus, Rep. Jamie Raskin joins to discuss the constitutional questions over the U.S. strike on Iran – and why Trump is now facing bipartisan blowback in Congress over taking the country to the brink without approval.

JD Vance is in Los Angeles as ICE raids ramp up and the Trump admin blocks members of Congress from detention facilities. Reps. Bennie Thompson and Judy Chu join The Weeknight to discuss. Plus, Democrats are reasserting their power as Trump considers military action in Iran – without getting approval from Congress. And the latest as a federal judges orders the release of pro-Palestinian activist Mahmoud Khalil from federal custody after over 100 days in detention.

Rep. Raja Krishnamoorthi joins The Weeknight to discuss the fight against Trump’s erosion of democratic norms -- and the alarming rise in political violence casting a shadow over our democracy. Plus, former State Dept. official Richard Stengel, retired Lieutenant Colonel Amy McGrath, and former republican Congressman Charlie Dent discuss the serious ramifications of Trump’s ill-prepared cabinet in the face of rising tensions in the Middle East.

Former Republican Communications Director Tara Setmayer and Corey Brettschneider, co-host of “The Oath and the Office” podcast join The Weeknight to discuss the Democratic Leadership’s response to Trump’s authoritarian tactics. Plus, Rep. Eric Swalwell weighs in on defense Secretary Pete Hegseth being grilled by Senate Democrats today.