SAN ANTONIO — It was 2 a.m., and Maya Rupert was famished.
Hours earlier, Julián Castro’s campaign manager, surrounded by eager journalists, had watched her candidate wrap up his first Democratic presidential debate and walk into the spin room. “He was mobbed,” Rupert recalled — with reporters from all backgrounds trying to get a few minutes with the presidential candidate that The New York Times said “won the night.”
She didn’t need the Times to tell her that. She had watched his entire performance and prepped with him beforehand. Before Castro’s team landed in Miami, Rupert knew Castro would double down on his immigration policy, address racial inequality and close with an “Adiós to Donald Trump” zinger — a half-joking nod to what Castro says he’d say to the president on Jan. 20, 2021, should he get elected to the White House — that elicited cheers from the studio audience.
But after the swarm of media had dispersed, Rupert went to her room. Her stomach wouldn’t let her relax; she was still anxious and felt nauseated from unrelenting hunger pangs that had hounded her since breakfast that morning. She went to a nearby CVS — “it was the only place that was open,” she said, laughing, “and I was just trying to get food” — and selected her meal for the night, a ham and cheese Lunchables, when Castro coincidentally entered the same store.
“Hey, Maya,” Castro said wryly, sans the tie he wore on the debate stage but still polished from the back-to-back media hits he had concluded just minutes before. “What did you think?”
All Rupert remembers doing next is screaming and giving him a hug.
“It was exactly what I wanted,” she told The Texas Tribune of Castro’s debate performance weeks later. “It was people getting a real chance to see his passion on the issues that he talks about. … It was great. It was really, really great.”
But Castro’s pivotal debate performance was momentous for Rupert, too. She has never spearheaded a political campaign, let alone a presidential one. And as one of the few black women ever tapped to be a presidential campaign manager, she knows there’s a lot riding on her shoulders. Not only does she have to help convince people to elect her candidate, but she’s gunning to prove that she’s the one who can help make it happen.
Her candidate’s breakout moment that evening — which led to glowing headlines and a hefty bump in campaign contributions — was just one step toward doing that.
Still, Rupert knows her job isn’t easy. She’s still not managing a frontrunner’s campaign — an underdog sentiment Castro, too, hasn’t shied away from embracing. On the night he took the debate stage, he was clustered alongside other Democratic dark horses, save for U.S. Sen. Elizabeth Warren of Massachusetts. He’ll be on another debate stage Wednesday night and needs a similarly strong performance to continue his momentum.
But Rupert knows her candidate’s polling numbers and less-than-stellar fundraising hauls won’t suffice as excuses if she falls flat — especially not for someone who looks like she does.
Her candidate is under a similar strain, Rupert said. As a person of color, he’s expected to exude authenticity with his Latino heritage (which, in Castro’s case, she said, may mean drilling down on immigration policy more than his white counterparts or speaking Spanish on the campaign trail) while also maintaining a squeaky clean presidential image.
Then Rupert put it bluntly: People of color don’t get an opportunity to “fail up,” she said. “We don’t get to screw up a little bit and then still end up where we are.”
While their long-shot status has put pressure on both their backs, it has also tethered the two together. It’s what makes Rupert and Castro such a unique duo: The former is a campaign rookie and the third black woman tapped to run a presidential campaign, behind Donna Brazile with Al Gore and Maggie Williams with Hillary Clinton. The latter is trying to become the first Latino president in U.S. history.
“It was not a foregone conclusion that I was going to be working for a candidate in 2020, and the question was for whom,” she said. “This is him.
“I’m doing this because it’s him.”
“We were just in sync”
In many ways, Rupert is an unconventional choice for a presidential campaign manager. She’s 38, she's bubbly, she’s a woman and she’s black. During an interview, Rupert couldn’t stop laughing as she recounted a time when Castro jokingly texted her a picture of a scorpion because he knew she’s terrified of bugs.
But her road to becoming his right-hand woman was no more by the books.
Although Rupert was born in Ohio, she considers herself a Californian. She moved to the Golden State when she was 1 year old. She grew up in Yucca Valley, a small desert town she described as predominantly white and low income.
Rupert always thought she’d stay on the West Coast. She earned her undergraduate degree at the University of California, Santa Barbara, and then went to law school at the University of California, Berkeley. She also thought she’d be an attorney her whole life. Politics, she said, was an enigma. It interested her from a distance but seemed elusive.
Although she did work as an attorney for a few years, Rupert knew her passion lay in policy work. That’s what led her to a job at the National Center for Lesbian Rights — a nonprofit legal organization that advocates for LGBTQ people and their families — for five years before she transitioned into a role with the U.S. Department of Housing and Urban Development.
“She was a superstar,” said Shannon Minter, her former supervisor at NCLR. “I used to tell her almost every day, ‘I know somebody is eventually going to steal you away from us.’”
When Rupert started at HUD in 2015, she didn’t know Castro. At the time, he was the housing secretary, appointed by then-President Barack Obama. When the two first met, Rupert was pushing for a rule — one stalled at the federal agency — allowing HUD-funded shelters to accept transgender people under their proper pronouns rather than the ones they were assigned at birth. She expected defiance since her efforts on the same policy proposal hadn’t made much headway while she was at NCLR.
But Castro saw eye to eye with Rupert. Then he went further. He asked Rupert how the proposal could be expanded beyond only HUD-funded shelters.
“I could tell she was an effective advocate,” Castro told the Tribune in a telephone interview on the way to a campaign event in New Hampshire. “As I came to know her and her work, I knew she had a knack for both the politics and the policy. I knew I could trust her to get the job done.
“We were just in sync.”
Rupert hailed Castro in a similar regard. She noted that it was during that meeting — the first time the two ever met face to face — that she came to the realization that the housing secretary would not only be an ally, but also a friend.
“I remember thinking, ‘Oh wow, I really like this guy,’” she said, smiling. “You can be a politician and still talk like one of us. It was very moving. I just thought, ‘Wow, I could work with him.’”
Shortly after, she did.
About six months into starting her job at HUD, Rupert was promoted to be one of Castro’s senior advisers — a role she held until the end of the Obama administration.
Nealin Parker, Castro’s chief of staff at HUD who worked to help promote Rupert, said that in Rupert’s new role, she was charged with delivering less-than-ideal news to the housing secretary — and coming up with solutions. In the secretary’s conference room — a room adjacent to his office — Rupert would sit with a grin on her face, waiting for the secretary to make an entrance.
“She was cool and calm. She would brief on issues with complete seriousness, but not drama,” Parker said. “She owned the ‘I wish I were bringing you something easy right now’ mentality.”
“He trusted her judgment, I trusted her judgement and she gave every reason for that trust,” she later added.
After Obama’s final term ended, Rupert took a gig with the Center for Reproductive Rights. But she knew that if her former boss wanted to do something — like, say, launch a bid for the White House — she’d come back to work with him in some undetermined capacity.
(Castro said the same. In separate interviews, both joked about a wisecrack he repeatedly made as housing secretary — one he’d tell throngs of people but not Rupert herself, she noted — that wherever he went after HUD, he hoped to continue working with her.)
That came to fruition in August 2018 when she began running his political action committee, Opportunity First. Shortly thereafter, when the two began daydreaming possibilities of what came next, campaign manager seemed out of reach — at least in her eyes. Rupert described herself as a policy wonk and said serving as the chief adviser to a presidential candidate seemed out of her wheelhouse. Castro thought otherwise.
“It’s true that she didn’t have classic campaign management experience,” he said. “But I was convinced. … She has a great grasp on the type of leadership the American people are looking for, as well as an ability to execute — which I saw at HUD. I was willing to take a chance.”
Then Rupert, too, began to see how she could fit into the mold.
“It’s hard to articulate how much this opportunity means. I know his vision, and I care immensely about what we’re doing,” she said of his campaign. “Plus, I knew I could identify the places where I was going to need additional help.”
While at HUD, Rupert was known as a problem solver. She hasn’t shaken that role as Castro’s campaign manager, and the No. 1 problem of her new job is a big one: How can she take an underdog candidate consistently polling in single digits and help him become the next president?
For the answer, she’s turning to her policy background and helping Castro roll out detailed proposals — and then waiting for other 2020 Democrats to follow his lead.
“In a field this crowded, you can sort of define yourself through policy. That’s where my expertise lies. When you’re a hammer, everything is a nail. I feel like the solution for everything,” she said, laughing, “is rolling out a policy proposal on it.”
Many of those proposals come from wonky discussions Rupert and Castro had before he even became a candidate. The heart of his immigration policy, which other Democratic candidates have embraced, stems from talks the pair had a year ago about ending detention as a mechanism for immigration enforcement.
His police reform plan comes in part from from their shared anger over police shootings in 2015 and 2016.
“This has been a priority for him for a while, but the idea of actually, explicitly addressing police violence was something I hugely wanted to see us do as well,” Rupert said.
The problem is Castro often is not recognized for his detailed policy work. He was the first candidate to roll out a comprehensive immigration plan. The first to release a plan to eliminate lead exposure. The first to challenge others in the Democratic primary field — including fellow Texan Beto O’Rourke — on their immigration credentials. But Rupert knows she needs to grow Castro’s name ID.
In interviews, Castro often refers to an alternative path to the White House. Part of that path is the campaign’s “Southwest strategy,” which addresses what she calls a false divide that presidential candidates can either appeal to “communities of color and young people or white, working-class voters,” she said.
She said the strategy targets states that often get written off — like Arizona and Texas — and encourages Castro to work on not only winning back states Democrats lost in 2016, but to win new states.
“Talking about education and adding in pieces that are particularly relevant to people of color is not going to turn off white, working-class voters who are also going to benefit from these exact same policies,” she said. “You don’t have to make it either-or.”
In that way, political experts agree: Rupert’s hiring was not only groundbreaking, but strategic. The Castro campaign, fronted by a Hispanic man and managed by a black woman, is banking on being in a unique position to reach and persuade voters of color, which can form powerful voting blocs capable of swinging elections.
“Maya knows we are a key constituent. If [Castro] is going to win, or at least make a mark, he has to make a way in the mark on African American women,” said Minyon Moore, a political strategist who previously worked for Bill Clinton’s administration. “I think having Maya is an added advantage [for Castro] because she knows her community.”
A shared mission
Rupert knows she’ll be judged no matter what happens with Castro, but also that her success or failure will affect others, too.
“One of the things that scares me — and it isn’t fair — is that this gets treated as a failed experiment,” she said. “I think about the next black woman who wants to do this job. I don’t want her to get compared to me. I do sit with that. I take that really seriously.”
And she’s running a campaign that’s aiming to go head to head with a president who recently made headlines for racist remarks like telling a group of congresswomen of color to “go back” to the “broken and crime infested places from which they came.”
“I can’t believe sometimes that’s the state of politics, as we get more and more diverse, that people are so explicitly racist,” Rupert said. “We’re past saying the quiet part out loud. I see those comments, and I’m infuriated.”
Castro discusses his race as a lived experience that forms his beliefs — perhaps most notably on immigration, especially as Trump uses the issue as a key talking point in bolstering his reelection campaign.
But today’s tumultuous political climate also forces Rupert to cheer a little louder when her candidate espouses his views on police accountability (he wants to collect better data on police stops), Flint (he was the first presidential candidate to visit the Michigan city years after its water crisis) and reparations for slavery (he supports a commission to study them).
The pair’s shared mission gives them an unbreakable bond that’s on full display when they’re together. It leads them to constantly needle each other when they’re together in the campaign headquarters. And it causes them to gleefully hug when they bump into each other after a successful debate. Rupert is hoping for more of those moments as soon as Wednesday night, and that the duo will be able to make history together.
“I want to run a campaign that will make him proud,” Rupert said. “I’m so proud every time I get to talk to young black women and I get to tell tell them what I’m doing. I love that moment. But I also want this to be a campaign the Latino community feels a lot of pride around.
“I want to make sure there’s a group of people,” she said, “who are looking at this and thinking — finally — ‘I got next.’”