Politics: You were with the president at the formative stages of his campaign in 2006. What was it like at a time when there weren't too many people who actually thought he'd be the next president?
Hildebrand: Well, I started with him in a real way in October of 2006. So I sat in those strategy meetings and helped write plans and budgets and that kind of stuff. In a selfish way for me, I had sort of lost faith in politics and government. It's like every cycle it gets a little worse, with politicians becoming less bold and more concerned about reelection. I had been working in politics for 22 years, and I was looking at what we were faced with--mounting deficits, crazy social policies, a lack of willingness to deal with climate change, and nothing had really changed in the way of gay rights in all that time. I was just growing impatient and basically I was looking for my one last hope. When I met Barack and saw the kind of passion that people had for him, I thought maybe he was different and maybe he was the guy who was the one last hope. Once I got to know him, I became a true believer in a very short period of time.
Politics: You say you don't like to take much credit for any of this, but you played a big role in crafting that original message, which stuck.
Hildebrand: But that doesn't make me the hero of getting him elected. I was one of thousands of staff people. Did I help craft some of the strategy? Yes. What I tried to impress upon people is that this guy is unique and the kind of leader we need at this time. That the core message never really changed wasn't because it was politically expedient. And while the television ads and the direct mail and everything that goes along with that is vitally important to the success of a campaign, I really do give a lot of the credit to the organizers who were out in the field, registering voters at a pace that's unheard of. If we hadn't done those kinds of very successful voter registration efforts, this guy would not be president.
Politics: A few months back on Huffington Post you penned a bit of criticism of progressives who were attacking some of the president's cabinet picks. How do you see his relationship with the progressive net-roots developing over the next few years?
Hildebrand: I should have changed a few words with that Huffington Post piece, and I didn't write the headline. But what I was trying to articulate was this: If you are a progressive in this country and you have a president whose top agenda items are putting people back to work, universal healthcare, addressing climate change, education and getting out of Iraq--that's a good enough list for a progressive person to say, "Thank God he's president." There are bigger issues that he needs to address right now. Let's work on the biggest, most impactful issues first and then worry about the others once we have accomplished some big things. I also think it's important to state that Barack Obama is not the president of the netroots, he's not the president of the grassroots--he is the president of the United States. He's going to do what he believes is best for the country, and more often than not it's going to please people in the progressive community. …