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.
Ah, gotcha.
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.
Talking about working in the White House and that Simmons podcast you were a guest on, I vaguely remember something you said about Hillary on it; obviously you guys had a very combative primary race against Clinton in 2008, and when she became part of the team as Secretary of State, you and others were a little bit skeptical of her. Then once you guys got familiar with her and started working with her you had a complete change of heart on how you feel about her.
Yeah, I just gained a lot of respect for her. It was a very difficult primary. Barack Obama won it, obviously, and I’m proud of the race we ran, but I also think in the heat of a campaign, each candidate is caricatured by the other side. I faced the challenge that a lot of Americans have faced. You see Hillary from afar and you’ve known about her for so long and you see what the media perception of her is, and I think she’s cautious by nature in how she speaks. A lot of people know about her but a lot of people don’t really know her. I remember those first couple cabinet meetings in the White House, and the cabinet would sit all around the table and all the staffers would sit around behind them or in the back of the room in the cheap seats. You listen to the cabinet meeting go on and Obama would go around to each cabinet secretary and ask for their thoughts on things. He’d get to Hillary and I was just always so impressed with her knowledge and her experience. She was always impeccably prepared.
I was also impressed by the people she surrounded herself with in the White House. We ended up getting along with her staff a lot better than I think any of us thought we would. Everyone got along with her a lot better than we thought we would. Obama believed in her before anyone else in the administration did. I think probably if you could poll most of the staff, “Should Obama pick Hillary as Secretary of State?” we all would have said, “No.” But he was the adult. He realized that they had a lot more in common than they did differences. And it was a good pick!
As someone who’s been so close to the epicenter of power in the United States, are there any things that the average person may not worry about that you worry about with a Trump presidency? You know, the stuff that isn’t so obvious like him starting wars over petty slights or launching nuclear attacks?
It’s hard to get past the worry that he’ll start wars and he’ll launch nuclear attacks.
[Laughter.] Yeah, that’s obviously huge.
Here’s the thing, I believed in Barack Obama when I started working for him because his beliefs on issues that I cared about lined up with my own. There was also an authenticity thing; I thought that this guy seems real. He doesn’t seem phony and bullshitty like a lot of politicians. Those were the reasons that I started working for him. Once he got to the White House, there was a third reason that I was so happy that he was there because he had the temperament and the personality for it. I would have underplayed those characteristics before I had been in the White House, but there were countless crises that he had to deal with over the next 8 years, and he was more cool than anyone who ever worked for him. He didn’t allow himself to be swayed by emotion or the news cycle.
Remember the BP oil spill? Everyone was going insane about this. It would rile all of us up at the White House, but the president didn’t rile up. You can’t rile up Barack Obama because he would sit there and be like, “I don’t care about the news cycle. I don’t care if I’m unpopular for a while. What I care about is fixing the problem. What I care about is making the right decision. I will make the right decision and if I lose because of that, then I lose because of it. Maybe I won’t. Maybe it’ll be the right decision.” He put the right decision before he put politics and what people thought of him and especially what conventional wisdom in Washington told him to do. I think Trump does not read beyond headlines. His knowledge is only as deep as what you would know if you passed by CNN while flipping channels and saw a chyron. Watching CNN on mute and just looking at the chyrons, that is the level of intelligence and knowledge that Donald Trump has.
Like a lot of Americans who are only scanning headlines on Facebook and forming opinions based on them. But those people aren’t trying to be president.
When you’re in the White House and you’re making life or death decisions every single day, you have to have some sort of moral internal compass and some level of basic knowledge to make sure that the decision you’re making is the right one. Trump doesn’t have that and he doesn’t surround himself with anyone who has that either.
Do you miss being in Obama’s inner circle at all? I know your life is completely different now. You live in LA. Things probably could not be more different than what it was during your time in the White House.
I miss it on the good days. My answer is I miss it on the good days, and I miss it on the bad days. The days that I don’t miss it are all the other days.
Interesting. What do you mean by that?
I miss it on the bad days because I’ll always have intense guilt that I’m not there to help out my pals, my friends that are still in the White House, and of course the President. I’m like, “I wish I was there to help everyone right now. I would pitch in because they’re going through a tough time.” On the good days, some of these incredible speeches that Obama’s given since I left, I’d be like, “Ah, I wish I was there to help with that speech.” I wish I was part of that because I had so much fun with those guys over the years and it would have been so great to stay up until 2 in the morning with them working on those speeches. All the days in between where nothing bad or good happened, and it was just a slog until late at night, I don’t miss that.
This is kind of a random question, but do you watch Veep? The HBO show?
Yeah, I do.
How close is the absurdity portrayed on that show to the real thing? Does any of it ring true to you at all?
Yeah, it does. A lot. Real politics is a cross between Veep and West Wing. It’s not quite as starry-eyed, music swelled in the background, idealistic as West Wing, and it’s not quite as cynical and screw-bally as Veep is. It’s somewhere in between. I think Veep captures something essential about politics that no other show has. And by the way, I think House of Cards is a complete joke. There’s no resemblance from anything that I’ve experienced.
Interesting!
Yeah, it’s so silly. It’s fun though. I watch House of Cards all the time, but it doesn’t resemble politics in any way.
When you look back at the past few years of your life do you ever pinch yourself and think, “Holy shit, I’ve been really lucky to have been in the right place at the right time?”
All the time. I also look back and I’m very grateful that there were a few people in politics who took a chance on me that, were it not for them, I wouldn’t be where I am today.
What do you think you would be doing? I think I remember reading something where you said that after working for John Kerry you were very close to just getting out of politics altogether.
I was always about to go to law school.
[Laughter.] Of course!
I still have LSAT prep book in my bookshelf that I will never use. It was, “Let’s go to law school because I don’t know what else to do.” I graduated from Holy Cross and was trying to figure out what to make of my life after that, and then I told my parents that I was going to work for Kerry. They were very supportive and they told me to make sure to go to law school after the Kerry campaign. Then I was like, “I want to take a chance and work with this guy, Barack Obama, in the Senate. Don’t worry, I’ll do this for a couple years and then I’ll go to law school because there’s no way Obama’s running for president in 2008 because he’s way too young and way too new.” And now here we are.
Incredible. Speaking of Obama, have you reached out to him about being on the podcast?
Obviously we’ll have to do it at some point. The podcast folks in us are desperate for him to do it, but the former staffers in us know how annoying it is to fill a media request.
I totally get that.
I feel bad about pushing it too hard because it’s us, and I know his time is valuable, but selfishly we would love to have him on. Next time I see the communications crew who are still in the White House, we might have to chat.
You can listen to the Keepin’ It 1600 podcast on Soundcloud or subscribe to it via iTunes.