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.

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.