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Former Speechwriter Remembers Obama’s ‘Hopey, Changey’ Years

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President Barack Obama smiles while making a joke during his speech at the White House Correspondents' Association dinner at the Washington Hilton Hotel, Saturday, May 3, 2014.

President Barack Obama smiles while making a joke during his speech at the White House Correspondents’ Association dinner at the Washington Hilton Hotel, Saturday, May 3, 2014.

AP Photo/Jacquelyn Martin

At just 26 years old, David Litt became the senior speechwriter for President Barack Obama in 2013 after writing speeches for senior White House officials, like Valerie Jarrett and William Daley.

“Just walking down the hall was this extraordinary experience,” Litt said Tuesday on Morning Shift. “Even though I wasn’t a very important person, I still felt the responsibility. You have to appreciate it but you still have to focus on the work.”

Litt has written some of Obama’s most memorable and funny speeches, like his jokes at the White House Correspondents’ Association dinner, and he now works for comedy website Funny or Die.

Litt joined Morning Shift host Tony Sarabia to recap his time with the Obama administration, give insight on writing for politicians, and explain his new book, Thanks, Obama: My Hopey, Changey White House Years.

On the book’s “hopey, changey” name

David Litt: My reason for giving it that subtitle is that it’s a phrase Sarah Palin used to use to mock Obama supporters like myself. She would say, “How’s that whole hopey, changey stuff working out for you?” I didn’t appreciate the tone, but it’s actually a pretty good question. After Trump won the election, I wanted to go back and really think about how I was part of this movement.

Spoiler alert: I think it did work better than Sarah Palin might’ve imagined. It was really worth analyzing that question and looking back and trying to make sense of this experience I had and that, really, we all had together.

On how doing the small stuff led up to the big gig

Litt: While I was working for Valerie Jarrett and other senior staff, the chief speechwriter for President Obama at the time, Jon Favreau, let me sit in on his team’s meetings. And I developed a niche for doing stuff that no one else wanted to do because they weren’t the big deal speeches: the weekly addresses at the end of the week or a video wishing America a happy Thanksgiving. To me, these were incredibly exciting, but for people who’d been there a few years, there were bigger fish to fry.

Then, in late 2011, speechwriter Jon Lovett, who was running all of joke-writing for the correspondents’ dinner, left for Hollywood, and I sort of, by default, became the token White House funny person.

On how to write something funny for a politician

Litt: Even for President Obama who had extraordinary comedic timing — both for a president, and frankly, just for a human being — part of the joke was that the president was telling a joke. And he recognized this. Sometimes, when we would suggest a joke to him, he’d say, “That would be funny if a comedian did it,” which was his firm but polite way of saying that he’s playing himself and that he’s not here to do an amateur night. That’s important for writers and politicians to remember.

On starting an international incident

Litt: I wrote a speech that was mostly jokes, but at the end, President Obama was saying something nice about reporters. The line I wrote was: “Reporters have risked everything to bring us stories from countries like Syria and Kenya, stories that need to be told.” I used Syria because it’s a hostile and dangerous and evil regime. And I used Kenya mostly because it sounds like Syria. I remember thinking, “Should I run this by someone in the National Security Council whether it’s a good idea to put these two countries in the same sentence,” but then I thought, “No, I’m the speechwriter. This is going to go great.”

It went great in the room, but then the next day, the Kenyan government read the transcript and demanded an official apology from the United States. In the end, an unnamed White House senior official had to take time out of their day to say, “Obviously, the situations in Kenya and Syria are very different,” which was White House official code for “Obviously, David is an idiot.”

This interview has been edited for brevity and clarity. Click the “play” button to listen to the entire conversation, which was adapted for the web by producer Arionne Nettles.

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