Maya Rupert working on her cellphone at Open City Cafe in Washington, D.C., on Friday, Feb. 1, 2019
Photo: Terrell Jermaine Starr/The Root

WASHINGTON, D.C.—When Maya Rupert walked into then-Housing and Urban Development Secretary Julián Castro’s office with a tricky problem to solve, she expected some resistance. It was November 2015, and the agency had long been mulling a rule that would require HUD-funded shelters to accept transgender people under their proper genders, not the ones they were assigned at birth. The rule had stalled inside HUD over concerns that cisgender men would falsely identify as female to enter shelters and assault female occupants, among other issues.

Before arriving at HUD, Rupert was working on the issue as policy director at the National Center for Lesbian Rights and felt HUD did not appreciate the dire situations homeless trans people faced. She was chief of staff at HUD’s general counsel’s office when she first sat down with Castro and his senior aides and still new to the bureaucracy when she made her argument.

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“I started to explain why this was so important and the fact that trans women in particular, trans women of color especially, deal with so much violence and that being able to access homeless shelters was such a huge issue,” Rupert recalls telling Castro at their first meeting before he cut her off. “‘No, no, no. I understand that. The problem is this rule would only get to HUD-funded shelters, so how do we get to every shelter?’ Then, I had one of those moments where I was like, ‘Oh, he’s one of us.’”

The rule was eventually approved in September 2016. Castro was so impressed with her handling of the issue he promoted her to be one of his senior aides in January of that year.

Rupert would work closely with Castro at HUD until January 2017. She went on to lead his PAC, Opportunity First, and then his presidential exploratory committee. So it came as no surprise when Castro asked her in December to be his campaign manager, making her one of the few black women to ever hold the position—and certainly one of the youngest, at 38 years old.

The role of campaign manager functions as something of a marriage. You’re handpicked for that job because, at least professionally, the candidate trusts you more than anyone else and believes you can steer them toward a promising path to victory and away from any dangers that could block it. You’re the engine of the campaign, the last line of defense. It is rarefied air breathed almost exclusively by white men.

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Donna Brazile, who in 2000 managed Al Gore’s campaign, and Maggie Williams, who came on toward the end of Hillary Rodham Clinton’s 2008 presidential run, are the two other black women known to have assumed the role. Unlike either of those women, Rupert isn’t managing a frontrunner—at least not yet.

Castro’s name hasn’t been mentioned with the likes of Kamala Harris, Elizabeth Warren, Bernie Sanders, and others. But that strengthens Rupert’s resolve. That’s why she sees her role as two-fold: convincing America that Castro should be their next president, and proving that a black woman can make it happen.

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“It’s definitely a lot of stress,” she told me recently over a Friday-afternoon meal at Open City in Washington, D.C. “I honestly do feel pressure about the fact that not a lot of black women have been in this position before. So I feel an added pressure to make sure anything I do doesn’t reflect negatively on the next black woman who could do this job.”

Christina Greer, associate professor of political science at Fordham University, characterized Rupert’s concerns more bluntly.

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“Anytime you are either the first or one of the few, obviously it is imperative you do a good job because we know that marginalized communities don’t get to fail upward like we see other people do,” she said.

Maya Rupert isn’t Megyn Kelly. And she knows it.


When I arrived at the cafe to meet Rupert, she was thumbing away at her cellphone, arranging meetings, mulling over key hires, suitcase in tow. She had just arrived from San Antonio, Castro’s campaign headquarters. She’s recently spent much of her time learning the intricacies of electoral politics and adjusting her advocacy skills to fit her new job.

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This is her first time running or working on a political campaign of any size, something she sees as an advantage because Americans have grown frustrated with machine politics. That frees her to be creative with how she promotes Castro, who she feels can make a real showing by creating a primary map to victory that has never been attempted.

Former HUD Secretary Julian Castro with Maya Rupert, his senior adviser, at HUD in 2016.
Photo: HUD

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Winning much of the black vote will be essential, but Rupert is also creating what she calls her “Southwest Strategy,” which will target Latinx voters in Arizona, Nevada, New Mexico, and Texas, Castro’s home state. Part of Castro’s narrative will be sharing how his grandmother emigrated from Mexico to San Antonio during the 1920s, and how his own working-class background resonates with Latinx voters who are increasingly becoming a powerful voting force nationally.

She even thinks Castro can challenge Harris in her home state of California if the campaign targets Latinx voters aggressively enough.

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Rupert’s run as campaign manager will be a test of how a young black woman can bring her unique personal and professional experiences to high-stakes politics beyond the voting booth. Over the past 10 years, black women have been the deciding factors in both of Barack Obama’s successful elections and several midterm races—including the special election that got Doug Jones his Senate victory in Alabama. But they have long complained about Democrats winning offices with their votes, then getting repaid with few—if any—policies that directly benefit them.

Rupert is sensitive to that charge and is working with Castro to craft a series of policy points specifically for black women.

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Then there is Castro’s Mexican heritage, something Trump has proven he’d have no issue exploiting to motivate his most racist supporters. Trump has questioned the qualifications of a federal judge because of the judge’s Mexican heritage and has referred to Mexicans as “rapists and murderers.”

“There are people in Trump’s base who will never support a candidate of color,” Rupert said. “There’s nothing a candidate of color can do to fix that. There’s a segment of people who buy into the rhetoric that Trump has been spouting. But what they also care about is, ‘I need access to healthcare.’ ‘This is what my kid is going through at school.’ They care about who is going to improve their lives. For those folks, there’s absolutely room to appeal to them.”

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Rupert was born in Cleveland, Ohio, before her parents moved to Yucca Valley, California, a small unincorporated town in San Bernardino County, when she was a year old. Her parents grew up poor in inner-city Cleveland and felt a less urban environment would prove better for their children. The downside was growing up in a mostly white community, where black people were a rare sight. The thought of politics never entered her mind until she got to University of California, Berkeley Law School. After earning her law degree, Rupert clerked in the 6th Circuit Court in Detroit for a year and moved back to California to work at a law firm for three years. In 2010, she moved to D.C., where she worked at the National Center for Lesbian Rights for five years before taking a senior adviser job at HUD in 2015.

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Donald Sherman, who worked with Rupert at HUD’s general counsel office before she moved on to work directly with Castro, praised Rupert’s temperament and skill for managing complex relationships in the office.

“To call her cool under pressure is an understatement,” Sherman, former senior counsel and Office of the General Counsel chief of staff at HUD, said of his former colleague. “She helps bring people into the fold and helps build unity among the team regardless of what’s going on. She was always a joy to work with and someone who helped us stay focused on the big picture.”

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Maya Rupert, on the left, speaking to then-HUD Secretary Julian Castro in their first meeting about the rule that would allow transgender people to enter shelters under their proper genders, November 2015
Photo: HUD

Nealin Parker, Castro’s chief of staff at HUD, said when issues get to the secretary’s office, they often are difficult to resolve. It was Rupert who was tasked with coming up with potential solutions. That included talking to the principles at the center of the challenge and reporting assessments and options to Parker and Castro for them to consider. Rupert flourished.

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“It’s fine to have bad news. But I don’t ever want to hear about it from anybody but you, and I want to hear about it fast,” Parker recalls telling Rupert. “She was working on the hardest things in HUD and I knew she was handling a huge amount of it. She spoke the truth and it wasn’t always pleasant. But it was always in service of getting to a better end.”

Those skills—dealing with unpleasantness—come in handy. Trump’s vitriolic views on race and women have made Rupert’s job with Castro very challenging, she told me. Trolls have harassed her on social media with racist and sexist insults, something that’s typical for women—especially black women—but the harassment has gotten much worse since she became Castro’s campaign manager. “Black bitch” and homophobic slurs she declined to name are some of the worst she has received.

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“Being in politics now, as a woman of color, means knowing that we will be a target for a particular kind of vitriol that has to be a part of my job,” she said.

She never responds. It’s a built-in defense mechanism. Every emotion a black woman expresses can be taken as a negative—especially passion, which falls squarely into the “angry black woman trope.”

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This campaign is about Castro, but Rupert is also working for the culture. Her first task with the campaign was creating a sexual harassment policy. She is trying to get the staff unionized as well. Every intern makes at least $15 an hour, a rule Rupert called for. These are all principles in which Castro believes strongly. But Rupert also wants marginalized people, including black women, to feel they can afford to work on a presidential campaign without suffering financially.

By helping to build Castro’s campaign into a contender, Rupert believes she is creating a space where black women can see themselves alongside her—or perhaps one day even assuming her role.

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“I want young black women to realize these are fields where you can come and be your entire self,” she said. “There are candidates that do not share your same identity who will value your experience and your perspective and will want to elevate you because they trust you.”