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.