In 2004 Jon Favreau (the former Obama speechwriter and podcast host, not the actor/director) was working for John Kerry, the Democratic nominee for president at the time, as a speechwriter. One day he was assigned to deliver some bad news to a young Senate candidate from Illinois named Barack Obama; a line from a speech Obama was to give at the Democratic National Convention needed to be cut out. How he came to be a person tasked with delivering this news to Obama was something of a fortunate accident.
“I basically only got the job because I was a press assistant on the campaign, and we were losing to Howard Dean, and the campaign was running out of money and there was a big shake-up and all these people got fired, and they needed a deputy speechwriter and at that point they couldn’t really afford to hire a real one,” Favreau wrote in New York magazine earlier this year. “No one really wanted to join what looked like a sinking ship.”
Kerry wound up losing the 2004 election to George W. Bush, but Obama won his race and soon needed a speechwriter for his Senate staff. The two met for an interview, one that Favreau termed “the most easygoing interview I’ve ever had,” and at the end Obama said, “You seem nice enough, so let’s give this a whirl.” The rest, as they say, is history.
Favreau left the Obama administration in 2013 to pursue a career as a private consultant, founding Fenway Strategies with Tommy Vietor, Obama’s former National Security Spokesman. And earlier this year he — along with co-host Dan Pfeiffer, a former Obama advisor — launched the Keepin’ It 1600 podcast on Bill Simmons’ The Ringer podcast network. Former Obama White House staffers Vietor and Jon Lovett are also regulars on the show. Together, the four former Obama White House colleagues discuss the 2016 election and politics in general. It’s become a must-listen for political junkies and people curious about the 2016 election.
We spoke to Favreau recently about the podcast, how he came to respect Hillary Clinton, and what it was like working for President Obama, among other things.
So how did it come to be that the guy who helped put words into the mouth of one of the more eloquent leaders in world history is now hosting a podcast?
I’ve known Bill [Simmons] since the first campaign, since Obama’s campaign in 2008, and that’s only because we both went to the same college, Holy Cross. He was still The Sports Guy writing for ESPN at the time and one day he wrote something along the lines of, “Oh, I heard that Obama’s speech writer is a Holy Cross grad, who’s also from the Boston area, like me.” I’d grown up reading his columns all the time, so I thought that was pretty cool. Then we got in touch through mutual friends. But I did not ever listen to podcasts when I lived in Washington, D. C. I sort of knew about Marc Maron’s podcast, but I wasn’t really a big podcast guy.
Why not? Did you just not have the time?
Mainly because I just didn’t drive many places. It’s a smaller city.
Then when I got to Los Angeles — I moved to Los Angeles about 2 years ago this week, actually — I ran into Simmons, who also lives here. He was like, “Oh, I gotta get you on the podcast to do an interview about the election since there’s so much interest in politics.” So, we do this interview on his podcast and after he was like, “You know, that went really well. What do you think about hosting a podcast for my new site, The Ringer? We don’t have anyone doing anything about politics or national affairs or anything like that.” My first reaction was that this could be a lot of fun, but also, how the hell do you do a podcast? I was like, I can do interviews pretty well at this point but I don’t know if I can host something. I don’t really have that skill. But I figured why not give it a whirl? I was at a point in my life where I was out of politics, and I was happy to be away from it. But once this election rolled around, and it had also been a couple years since I’d been involved in politics, I started missing it a lot. I missed talking about it and writing about it. It was a perfect opportunity and perfect outlet to continue ranting about politics, especially during this election when there’s so much to say.
Yeah, “so much to say” is kind of an understatement.
So Dan [Pfeiffer] and I just sort of started it up. The podcast basically was just an audio version for everyone else to hear the conversations that Dan and I would have all the time. We’d have this conversation also with Tommy Vietor and Jon Lovett, who also became part of the podcast. It was only natural. The four of us have spent most of our days, or a lot of our days, talking about politics to each other and we have for a long time ever since we left the White House.
I suppose that’s part of the reason why it works so well is, like you said, you guys have all been buddies for so long and you’re just kind of naturally having the conversations that you would have anyway. It actually makes perfect sense when you put it that way.
It was a perfect fit, this crew of Obama White House alumni deciding that we’d start up a podcast.