Countdown’s Keith Olbermann joins us to talk about Trump’s latest bloviating and the potential for him to open his mouth and get into even more trouble. Then we’re joined by The New York Times Magazine’s Robert Draper, the author of Weapon of Mass Delusion: When The Republican Party Lost Its Mind to talk about the GOP’s descent into madness. Then Rep. Patrick Ryan of New York’s 19th congressional district tells us about his competitive race.