Obama Roasts Trump at White House Correspondents' Dinner

The Setup

The 2011 White House Correspondents’ Dinner took place on April 30 (with coverage running into May 1), just three days after President Obama had released his long-form birth certificate in direct response to Trump’s birther campaign. Trump attended the dinner as a guest of the Washington Post, seated prominently in the ballroom of the Washington Hilton. The combination of Trump’s presence and the birther controversy’s climax created an extraordinary moment in American political theater.

What Trump did not know was that Obama had spent part of the previous days preparing jokes aimed directly at him. Nor did Trump know that at that very moment, Navy SEALs were preparing to raid a compound in Abbottabad, Pakistan, where intelligence indicated Osama bin Laden was hiding. Obama had authorized the raid earlier that day.

The Roast

Obama devoted a sustained portion of his comedy monologue to Trump. With cameras trained on Trump’s face, Obama began by noting that Trump could finally “get back to focusing on the issues that matter, like did we fake the moon landing, what really happened in Roswell, and where are Biggie and Tupac?”

Obama then mocked Trump’s credentials, joking about an episode of Celebrity Apprentice in which Trump had to decide between the competing claims of two contestants. “These are the kind of decisions that would keep me up at night,” Obama deadpanned. “Well handled, sir.” The room erupted in laughter while Trump sat largely expressionless, his jaw set.

Comedian Seth Meyers, the evening’s featured entertainer, continued the assault. “Donald Trump has been saying he will run for president as a Republican, which is surprising since I just assumed he was running as a joke,” Meyers said. Trump did not smile.

The Aftermath and Its Legacy

The dinner became one of the most analyzed social moments in modern political history. Many commentators and Trump associates later speculated that the humiliation Trump experienced that evening hardened his determination to run for president and to dismantle Obama’s legacy. Trump himself has dismissed this theory, but multiple accounts from people close to him describe the dinner as a pivotal emotional experience.

The moment also revealed the Washington establishment’s failure to take Trump seriously as a political threat. The laughter in the room reflected a bipartisan consensus that Trump’s political ambitions were absurd. Within four years, he would secure the Republican nomination. Within five, he would be president. The Correspondents’ Dinner roast became, in retrospect, less a moment of triumph for Obama than an illustration of how thoroughly the political class misjudged the forces Trump was riding.