“Dan Included the D— Joke”: Obama’s Improv Jab at Trump Finally Explained

Who could forget former President Barack Obama’s playful jab at Donald Trump during his 2016 Democratic National Convention (DNC) speech? The moment when Obama mocked Trump’s obsession with “crowd size” became an instant hit, but until now, no one knew the origins of the suggestively lewd hand gesture that accompanied the joke.

In a recent interview on Pod Save America, the mystery was finally revealed. Former Obama speechwriter Jon Favreau shed light on how the now-famous joke came to be. He explained, “I should disclose, once a staffer, always a staffer, I volunteered to help a little, look at the speech a couple of times.” However, it wasn’t Favreau who devised the joke.

According to the Daily Beast, Dan Pfeiffer, Obama’s former communications director, was the mastermind behind the cheeky moment. According to Favreau, “Dan included the d— joke. Just so you all know, that was just in the moment. He just put his hands on the podium.” This hand gesture, which was clearly off-script, became an instant talking point.

Favreau clarified that the joke was improvised during the speech and wasn’t planned in advance. Speaker Jon Lovett humorously speculated, “Or maybe he knew all along that that was a d— joke and nobody else did but him.” Regardless, the joke landed perfectly, capturing the humor and charm that made Obama’s speeches so memorable.

The hosts agreed that this DNC speech was one of the most “persuasive” of the event, helping to rally Democratic support behind the Harris-Walz campaign. Obama’s ability to poke fun at Trump wasn’t a new phenomenon. Back in 2011, during the White House Correspondents’ Dinner, Obama famously roasted Trump, who was present but notably silent throughout the event.

During that speech, Obama humorously pondered Trump’s interests, joking, “Like, did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac?” The jokes didn’t sit well with Trump, who later admitted that he appeared unamused because he wasn’t “looking to laugh along with my enemies.” Trump felt targeted, calling the event “a roast of Donald Trump.”

According to the New York Times, Trump reflected on his political identity, saying he saw himself as a “traditionalist with a liberal mindset” and even boasted of having “gay friends.” Before his rise as the Republican frontrunner, Trump considered himself a “conservative with a big heart,” a sentiment he carried into his political career. The humorous exchanges between Obama and Trump have become legendary, showcasing their starkly different styles and how a single joke can leave a lasting impact.