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Former Obama Staffers Dan Pfeiffer and Alyssa Mastromonaco on How DC Has Changed

"Having worked in the White House, I never really thought I would protest the White House."
Alyssa Mastromonaco and Dan Pfeiffer. Photograph of Mastromonaco by Ismael Quintanilla/Getty Images.

Pod Save America cohost Dan Pfeiffer, formerly President Obama’s communications director, is returning to DC to promote his new book, which looks at the lead-up to the 2016 election and recommends next steps for Democrats. At an event at Sixth & I on July 10, he’ll chat with old friend—and Obama’s onetime deputy chief of staff—Alyssa Mastromonaco ($15). Neither lives in Washington anymore, but both have plenty of thoughts on what’s happening here.

On how DC has changed post-Obama

Pfeiffer: I always like to distinguish between the city of Washington and the town of Washington. The city has never been doing better—it feels the same as when Obama was there. If you walk down 14th Street, Logan Circle, or the U Street corridor, it feels joyous and happy and avant-garde and progressive. I make a very strong effort not to go to places where the Trump staff or lobbyists would hang out because, frankly, who needs that in their life?

On what it’s like watching the Trump chaos from afar

Mastromonaco: Having worked in the White House, I never really thought I would protest the White House. Once you work there, you have great empathy for those who came before you. You know how hard it is, and you always try to give people a chance. But probably half the visits I’ve made to Washington [in the Trump era] were to march. It’s a bummer.

Pfeiffer: If you’ve actually been inside the walls of the White House, know how it works, know the sorts of decisions that Presidents have to make and the timeline on which they have to make them, you know it’s so much worse than you can even imagine just reading the news.

On being back in DC together

Pfeiffer: It will be a nice trip down memory lane. We laugh a lot; we try to explain the inside jokes to everyone. It’s the event I’m most looking forward to on my book tour.

Mastromonaco: Yeah, I can’t wait. Only Dan could get me to DC in July.

This article appeared in the July 2018 issue of Washingtonian.

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Assistant Editor

Mimi Montgomery joined Washingtonian in 2018. She previously was the editorial assistant at Walter Magazine in Raleigh, North Carolina, and freelanced for PoPVille and DCist. She lives in Adams Morgan.