An interview with the co-host of Keepin’ It 1600, which might just be the best political podcast out there.
It was April 2011, and the absurd controversy over President Obama’s birthplace—was it Hawaii? Kenya???—was in full swing. At the insistence of a rowdy band of conspiracy theorists led by one Donald Trump, the White House released the president’s birth certificate just days before the annual White House Correspondents’ Dinner, where Obama was due to speak. Knowing Trump would be in attendance, his aides, including head speechwriter Jon Favreau, decided to write in some digs at Trump’s expense.
“No one is happier about this than The Donald," Obama told the crowd. "Because he can 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?"
Trump sat stone-faced, absorbing the waves of laughter with all the grace of a Tupac truther. It was then, some say, that he decided to exact revenge on Obama, the bastards who penned the roast, the totally biased journalists laughing—and, really, the entire world—by running for president four years later.
On the popular Keepin’ It 1600 podcast, Favreau and co-host Dan Pfeiffer, another former Obama aide, do their best to make sense of the fallout of that night, otherwise known as the 2016 presidential election. Strewn with fucks, insanes, and fucking insane!s, the show is a glimpse into the Washington political scene after hours, a raucous happy hour where picklebacks are $5 and political chatter flows unfiltered. So is Favreau, the 35-year-old wunderkind who left the White House in 2013, to blame for unleashing Trump on American democracy? We go straight to the source.
GQ: You helped write President Obama’s 2011 White House Correspondent’s Dinner speech roasting Donald Trump, which some say goaded him into running for president. Are you responsible for giving us Trump?
Jon Favreau: I don’t know if I should say you’re welcome, or sorry. [laughs] I don't think that [roast] was responsible for Trump. I think whether he was humiliated at that dinner or not, he would have been humiliated in other ways, which would have led him to run. But look, we had some fun with him at that dinner because the birther conspiracy that launched it all, that happened that week. So we decided to poke fun at it.
This whole cycle has been an endless series of “what the fuck is happening.” What has surprised you the most?
That's a good question, because nothing surprises me anymore. [laughs] The depths to which Trump has sunk have surprised me. Every time he does something that seems completely offensive and disgraceful, there's always just one more rung in the ladder that he hasn't hit yet. [laughs] Particularly the attack on a Gold Star family, I think, was truly awful, and surprising even for Trump.
There was a lot of speculation, when that controversy persisted, that it would be his downfall. Do you think that's the case?
It’s certainly affected his standing in the race probably more than any other comment he’s made. It wasn't an attack on Hillary Clinton. It was an attack on an American. And a parent who lost a child who was serving this country honorably. So I think that did quite a bit.
Tell me about the story behind Keepin’ It 1600. How did it come about?
I’ve known Bill Simmons for a while. We both went to Holy Cross, and are from Boston. So we knew each other for a while. When I moved out to L.A., we kept in touch. And then one day he was like, "You've gotta come on the podcast." And I said sure. He also knew Pfeiffer from before, so he said, "Why don't you come on with Dan Pfeiffer, and we'll do an interview." So we did Bill Simmons' podcast. And he said, "We're starting The Ringer, what if you guys started your own podcast?" Aside from Simmons' podcast and maybe a few others, I didn't really listen to podcasts or understand them that much. And I didn't know if I'd be able to do one. But I said sure, because it sounded interesting, and I love talking about politics. And so we decided to test it out. And we had a lot of fun, and people seemed to like it, so we kept doing it.
What made you think, 'Okay, this is something I could do every week"?
I've done cable TV hits, and on television, you get a few minutes to fit everything in at once. And on a podcast, you have a much longer period of time to just have an interesting conversation about politics. That's all we wanted to do. And every time we bring guests on that's what we want to do. We think that a lot of commentary and punditry that you see on TV is neither informative nor entertaining, so we were like, "Why don't we just have the conversation that we have privately among our friends about politics with everyone else, and see if they're interested?" It's just a lot of talking like Dan and I would talk if we were hanging out, seeing each other in person.
Do you think that's why it's caught on? That it's this missing element from the political conversation?
I do. I think all these podcasts, a lot of great political podcasts that are out there right now, they share the same quality, which is there's an authenticity to the conversation that you don't always get in political commentary. And there's a deeper dive into certain issues and news events that you don't often have time for in other mediums.
What drew you back into politics? You left a couple of years ago. What made you want to get back into it?
I've been bitten by the bug, and that doesn't go away. When I left the White House, I was pretty eager to step away from all of this, because I was just tired. But after about a year I learned that I will probably never be able to give it up fully. I'll have other things that I do in life, other jobs, but I will always be fascinated with politics and want to talk about it, not just because it's interesting, but because I really care about all these issues. And I care about who wins, and I think it matters. And that's not something that goes away too easily.
"A lot of great political podcasts that are out there right now, they share the same quality, which is there's an authenticity to the conversation that you don't always get in political commentary."
How has living in LA, outside the Beltway, changed the way you look at politics now that you're back in it?
Whether I ended up moving to LA, or moving 10 miles out of D.C. in Virginia somewhere, there's a perspective you gain by being out of Washington and being out of politics in an official capacity, where you get more perspective and more context about what matters, what to worry about, what not to worry about. When you're in D.C. you can very easily get caught up in the insanity of the news cycle, and think that every single little gaffe and development matters in a big way. And a lot of it doesn't.
You always have to be able to see the big picture. And you also have to be able to see politics from a vantage point of how other people see politics, who are not necessarily political nerds like we all are. You realize that other Americans consume the news sporadically, and if you start consuming the news more sporadically, or if you see how other people consume the news, it gives you perspective.
There’s been speculation as to whether Trump will actually do the debates, but let’s say they do happen. What do Clinton and Trump each need to do to make the best case for themselves?
Hillary just needs to do two things. One, remind people of what her vision is for the country, and what her policy agenda is. And two, to remind people that Donald Trump is not qualified in any way to become president of the United States. He's not qualified to run for any office, let alone president of the United States. Those are her two main objectives in those debates.
Trump needs a personality transplant. [laughs] If he emerges in the debates as an entirely new personality, maybe he has a shot. He has to hope for a new personality and collective amnesia. Those are the two things he needs to have going for him and he'll be all set.
What do you think is the funniest Trump joke that will always be funny, no matter what?
His Twitter feed. I thought that Hillary's line at the convention, "a man you can bait with a tweet is not the man who should have nuclear weapons," is probably the most dead-on. If you're ever feeling down, scrolling through Donald Trump's Twitter feed will pick you right back up. [laughs]
You and Dan Pfieffer, your co-host, joke a lot about the state of the election, and seem generally confident that Hillary will come out on top. Do you ever despair that Trump will beat the odds and win this thing?
Oh, yeah. You have to run scared. President Obama said that this week. There’s a balance between complacency and freaking out. And I think, on one hand, if you just follow the news and follow the punditry, you could be whipped back and forth in 20 different directions 20 times a day. You need to look at the fundamentals, you need to look at the data. Look at the overall indicators of where the race is going, and all the polls. So you comfort yourself with all of that, but then you think, nothing is certain. Everything depends on people showing up at the polls and voting. So you've gotta work your ass off and run scared that way.
How has it felt to be in the final year of Obama’s presidency? Is it emotional?
Lot of nostalgia lately, as we're winding down these last couple months. I felt it at the convention when I saw everyone and I saw him again. There's a lot of pride in what he's accomplished, and there's a lot of nostalgia for how this all started, this very unlikely journey. It’s bittersweet.
Obama has given so many noteworthy speeches. Which do you think will be the most remembered a hundred years from now?
I still think his 2004 convention speech that launched him onto the national stage will be a speech that people remember forever. It is one of the most patriotic American speeches that I've ever heard. And the reason it is is because of who he was, his unlikely story, and what it said about the possibilities of America. It's not about whether we reach the ideal that he laid out in his speech, it's about whether we're on the journey toward those ideals, and whether we make progress in this country. That's what his presidency is about, and I think that's what we'll be talking about for quite some time.
This interview has been edited and condensed.