It's time to play Guess The Village Scion

YN: Where did you go to high school?

RW: I actually did five years of high school. Two years at Georgetown Day School here in town, and then I decided I wanted to become a hockey player, so I went up to boarding school, repeated my sophomore year. It’s a normal thing usually to do in boarding school, so I did three years at Hotchkiss up in Connecticut.

YN: So you obviously grew up — your father was the son of immigrants — you grew up fairly privileged and went to a really quality high school and then a boarding school. Do you think that’s impacted that political philosophy at all, just even being around other people who are generally more privileged?

RW: So, at the boarding school they were definitely more conservative. A lot of the sons of Wall Street and daughters of Wall Street type of people. But Georgetown Day School was uber-liberal. You’re calling your teachers by their first names there. In my class, you have Zach Beauchamp who was at TPM [Talking Points Memo] for a while. It’s a very liberal school. So I don’t think it influenced my politics in the sense of it influenced my understanding of the world, it influenced what I read and the people I was talking to ... but if GDS impacted my politics, I’d be a liberal right now.

YN: When you were at GDS, did you already consider yourself a conservative?

RW: I don’t think I had a leaning when I was there, really. I think I was too young, really. It wasn’t until I got to Hotchkiss. And then Haverford College is uber-liberal as well.

YN: Were you politically active in college?

RW: No, I volunteered for the McCain campaign when I was in college. I voted Republican when I was in college. But there wasn’t even a college Republican club on my campus. That club didn’t even exist. I think they’ve started it since I’ve left. I was not, though, doing debates with Democrats.

YN: ... Another way to get at the question is, what’s been your first-hand observation of your dad’s political views? He was at NPR. He certainly has never identified as a conservative.

RW: No, no, no. My dad — I would call him a blue-dog Dem if I had to classify it. He definitely is more liberal than I am. But I think it has to do with his life story. He was an immigrant from Panama, came here when he was 3, grew up in the projects of New York.

He really found opportunity through scholarships to schools, so he sees the value of having a social safety net. And then he sees the good that the government can do in his eyes, but he still thinks you have to work to take advantage of it and to make the most of it. That’s why I think he’s supportive of things like Obamacare or having welfare and that kind of stuff. So he lives his American dream in that, and I think seeing him achieve his American dream made me be conservative because I think there’s a lot of personal responsibility that leads to that, that leads to success.

And I think that it’s not a bad thing to have a social safety net — I think it’s important — but I think that having one that is too big does not push people to be the best they can be, does not encourage success in the way that I think is important. And I think his parents played a large role in encouraging him to have personal responsibility and personal drive.