Presidential speechwriter David Litt's comic account of his years spent working with Barack Obama and his reflection on Obama's legacy in the age of Trump. Like many twentysomethings, David Litt frequently embarrassed himself in front of his boss's boss. Unlike many twentysomethings, Litt's boss's boss was President Obama. At age twenty-four, Litt became one of the youngest White House speechwriters in history. Along with remarks on issues like climate change and criminal justice reform, he was the president's go-to writer for comedy. As the lead on the White House Correspondents' Dinner speech, he was responsible for some of President Obama's most memorable moments. Litt takes us inside his eight years on the front lines of Obamaworld. He goes from starry-eyed college student to nervous junior speechwriter to White House senior staff. His behind-the-scenes anecdotes answer questions like: What's the classiest White House men's room? What's the social scene like on Air Force One? David Litt has written for The Onion, McSweeney's, I Cosmopolitan, Vanity Fair, The Atlantic, and the New York Times.