Four former aides to President Obama — Jon Favreau, Dan Pfeiffer, Jon Lovett, and Tommy Vietor — are joined by journalists, politicians, comedians, and activists for a freewheeling conversation about politics, the press and the challenges posed by the Trump presidency.

Supreme Court Justice Anthony Kennedy retires, Trump and McConnell look to fill the seat before the midterms, and Congressional candidate Alexandria Ocasio-Cortez wins a major upset in the New York primary. Then Nevada Senator Catherine Cortez Masto joins Jon and Dan to talk about the Supreme Court fight and her recent trip to a detention center on the border.