But Rupert is hoping to make some history of her own, as well. She is just the third black woman to run a presidential campaign — Donna Brazile managed Al Gore’s campaign in 2000, and Maggie Williams managed part of Hillary Clinton’s 2008 run.
Castro, the former housing secretary, is running far behind in public opinion polls and fundraising. But he is campaigning steadily, and he recently met the donor and polling requirements for the first Democratic debate, likely securing him a spot and giving him a chance to broaden his reach with voters.
Rupert previously worked at various groups dealing with economic, racial and social issues, but this is her first time working on a campaign. The transition to electoral politics has been a seamless one, she says, because she sees her new job as a continuation of her career-long fight for justice.
Rupert recently spoke with The New York Times about how this election is different from past cycles and the role race will play, both as a policy issue and on the Democratic stage. (This interview has been edited and condensed.)
Q: Is it strange to you that it’s 2019, and it’s still so rare to be a black woman running a presidential campaign?
A: It’s real strange to me. I know so many amazing black women, like, we’ve got to get on this. But I also have a lot of hope that that’s changing. People are realizing how critical it is for campaigns and their leadership teams to reflect the communities that they are trying to resonate with.
Secretary Castro always puts together diverse teams, so I know that his commitment is a genuine one. I’m sure that there are some people who are hiring from an optics perspective of having a diverse team this cycle. What people are going to see, though, is that in order to be successful, you need a diverse team. It’s so much more than just hiring a diverse pool because it’s the moment to do it.
Q: What challenges do people of color who run for office face that white candidates don’t?
A: There are a couple of things. I think the American public metabolizes conversations about race being led by white people differently than they do when those same conversations are being led by people of color. I think there’s greater comfort, in some ways, hearing from a white candidate talking about how we need to confront white nationalism, and there’s discomfort when that same rhetoric comes from a candidate of color. We definitely grapple with how can Secretary Castro talk about race and racism in a way that is true to him and his experience, without being resisted in a way that white candidates just don’t have to deal with.
The other is a little bit more subtle. Right now there’s a lot of conversation around this idea of authenticity. Well, the tough thing about being a person of color in this country, is that one of the first things you learn in order to succeed is that you can’t always be exactly who you are. We’re conditioned to a certain level of inauthenticity. And so, to suddenly be told that thing that made it so that you could succeed is now going to become a liability, is challenging.
Secretary Castro tells the story about how people think he’s too squeaky clean, and he responds that he comes from a place where you don’t get second chances. We don’t get the opportunity to just fail up. If you messed up, that could be it. There’s a cruel irony to people of color growing up being told you have to be twice as good to get half as much. It’s so tied up in the way that we understand and perceive professionalism and whiteness as more closely aligned.
Q: How did you feel when you saw that Joe Biden released a campaign announcement video in Spanish?
A: It’s a sign of the times. I think that people recognize that Latino voters will have a huge say in how this cycle plays out, and I think a move like that is a signal that this is a community that no one can take for granted. You can’t run for president and not speak to the Latinx community.
Q: Do you see that as someone stepping in your lane? Competing for your votes?
A: From an electoral standpoint, it’s positive, it’s how we get a better policy. As far as a competition thing, I don’t see that as a single lane. There’s this weird dichotomy that we keep getting told, that you can either compete for folks of color or for white folks in the Midwest. I think that’s a false choice, and I think one of the most effective things Secretary Castro has done is point out that false choice.
For example, everybody has an affordability crisis, and it manifests itself in a different ways. We don’t treat issues as taking them out of a bucket and addressing them. We really want to get at the root cause and talk about how all these things are related. You can’t talk about college affordability without talking about the achievement gap, or bettering teaching as a profession, or addressing the school-to-prison pipeline. You have to look at it more holistically.
Q: With this primary field being the most diverse in history, do you think a white man could win the Democratic nomination for president?
A: I definitely think so. I’m always a little surprised at questions like that, because not only can he, history shows us that there’s a huge advantage. The idea that somehow being a white man has suddenly become a disadvantage is distracting from what the real project of representation is.
The way white men who are running answer that question, though, will be very telling. Because I think that no one will be able to be successful without acknowledging — given a field this diverse, and given the changing demographics — if they are the right person at this time. I think we would be doing ourselves a disservice to think somehow being a white man has now become something that they’re going to have to overcome.
Q: Are you worried about building momentum for Mr. Castro?
A: Honestly, no. Every day we talk to more people who are having the exact same reaction: They like these ideas, and they want to make sure that his ideas are the ones getting talked about.
We just came back from She The People, which was the first-ever presidential forum specifically for women of color. Working for a candidate whose ideas resonate with this constituency, I was so thrilled because he got to air some of these ideas with folks who make up the backbone of the Democratic Party.
I would rather have moments like that, where his message resonates with the women who are going to be the organizers for this election, who are going to be the people setting the tone, demanding answers and pushing things forward. I would rather see him be a top-tier candidate in a moment like that than anything else.
This article originally appeared in The New York Times.