Jen O’Malley Dillon & Maya Rupert Are Setting The Tone On The 2020 Campaign Trail

Maya Rupert on the campaign trail for Julián Castro. Courtesy of the Castro campaign.

Political strategist Jen O’Malley Dillon’s mentors told her that if she planned to get pregnant, she’d have to sit out former President Barack Obama’s re-election. O’Malley Dillon ignored their advice and in 2011, joined the campaign as deputy campaign manager. The following year, she got pregnant — with twins. “The first thing I remember saying when I was telling my boss was, ‘I have something to tell you. It's going to be hard. You're going to be upset about it, but it's going to be okay,’” O’Malley Dillon recalls.

“From then to now, I think there's a big difference,” she tells Bustle of the cultural shift in campaign world. A recent analysis by Politico found that the 2020 Democratic campaigns were boasting increased gender parity and pay equity among those in senior roles, with the notable exception of campaign managers. Only five of the remaining 20 Democratic candidates’ campaigns have women at the helm: Julián Castro, Beto O’Rourke, Tulsi Gabbard, Tom Steyer, and Steve Bullock. Of those candidates, Castro and O’Rourke are the only two to have consistently qualified for debates.

Maya Rupert, Castro’s campaign manager, comes to the role through the social justice movement. She worked as an attorney before transitioning to policy work at the National Center for Lesbian Rights, and later, the Department of Housing and Urban Development (HUD). That’s where she met Castro, who was serving as secretary of the department under Obama.

“My foray into electoral politics is because I fundamentally believe in him,” Rupert says of Castro. “I wanted to do something where I was able to center and fight for justice and I never thought electoral politics honestly was a path to that until I met him.”

By contrast, O’Malley Dillon, who is managing O’Rourke’s campaign, came up through the ranks of electoral politics. She was the battleground state director for Obama in 2008, then served as executive director of the Democratic National Committee before signing onto Obama’s re-election campaign. She says she didn’t plan to commit to a 2020 campaign, but after meeting with O’Rourke she was taken by the former congressman’s ability to listen, and by how much they aligned on their visions for the presidential race. “I was really pretty blown away,” she tells Bustle.

O’Malley Dillon and Rupert took vastly different paths to the helm of their respective campaigns. But each is making the role their own, implicitly challenging the status quo, and offering new visions of what leadership can look like. Bustle spoke with the two campaign managers about their experience navigating this competitive Democratic presidential primary, who they rely on for counsel and support, and what they think it will take to have more women lead campaigns for the highest office in the United States.

“Let’s Talk About Being An Older Mom”

Jen O'Malley Dillon at the headquarters of former President Obama's 2012 re-election campaign. AP/Shutterstock

O’Malley Dillon feels a responsibility to be transparent with others about the realities of being a woman who wants to both campaign and have a family. “Let's talk about fertility. Let's talk about being an older mom,” she says. “Let's talk about moving three kids to a whole new place and how I'm juggling it.”

Her candor is a radical departure from the old-school campaign culture she cut her teeth in. “There was just the sense that if you were talking about [motherhood], thinking about it, that clearly politics wasn't your first priority,” O’Malley Dillon says.

Her own experience is proof that such thinking is outdated. But that’s not to say her decision to join the O’Rourke campaign was an easy one. As she considered signing on for 2020, she mulled over just what that would mean for her family. She’d have to uproot everyone to Texas, her two oldest children would begin first grade in a new place, and her baby was, well, a baby. “How do we give routine and normalcy,” O’Malley Dillon wondered, “while being in a profession where there is no routine or normalcy?”

She had other concerns about getting back on the campaign trail, too. O’Malley Dillon was happily working at Precision Strategies, a Democratic consulting group she had co-founded. “I really had to come to peace with knowing that I was walking away from something that I really believed in and love doing every day,” she says. "I just ultimately felt like I couldn't look my kids in the eyes and not tell them that when we were facing Donald Trump, that I didn't do everything I possibly could to try to get him out of office.”

"There could not be a more important time for young women, for young women of color, for young black women to feel like they should be coming into this industry and shaking things up."

Even though O’Malley Dillon has spent much of her adult life on campaigns, the manager role has brought new challenges. To face them, she has relied on a network of women who have been in the trenches with her. Many of those women may not support O’Rourke, but they support O’Malley Dillon. “It's isolating to be a boss, just in general,” she says.

After the first primary debate, O’Malley Dillon needed to hit the so-called “spin room” and talk to reporters about her candidate’s performance, which is not her normal role. So she called on Christina Reynolds, the vice president of communications for the political organization EMILY’s List, to help her prepare. “What do I need to know? How do I think about this?” O’Malley Dillon recalls asking Reynolds. Then there were the less substantive, but equally stressful, questions about how to put herself out in front of the public. “I knew I could be like, ‘I'm not sure what to wear. Should I do hair and makeup?’ Like all this stupid s*** that you're not going to have a conversation with staff about but you need somebody to kind of double check. Like, do I really need jewel tones in my dress?” she says.

There are some challenges no one can fully prepare you for, though. Dealing with the aftermath of the El Paso shooting, a racist attack that left 22 people dead, required O’Malley Dillon to summon her own sense of leadership. She worked to support her candidate as he comforted the grieving community he used to represent in Congress, while also acknowledging the needs of her staff. “I immediately called the team together, talked about taking care of yourself, being with each other,” O’Malley Dillon says. At the same time, she had to keep the ship afloat and deal with the realities of putting fundraising and political events on hold while the candidate focused on his hometown.

When it comes to balancing the demands of the job and the realities of motherhood — on the day she spoke with Bustle, she was expecting a visit from the tooth fairy — O’Malley Dillon finds comfort in knowing that there are other moms in senior roles, including Emmy Ruiz, a senior adviser to Kamala Harris, and Jess O’Connell, a senior adviser to Pete Buttigieg.

“You see texts or tweets about missing the kids or seeing the kids, and you know you're all going through it,” O’Malley Dillon says. “You all know how hard it is and you know, wherever and whoever we're working on, there's just such a deep support network that has really helped me be able to handle this.”

“If I Kept Replicating That, It Would Never Stop”

Maya Rupert at work with Julián Castro. Courtesy of the Castro campaign.

In August, after Rep. Joaquin Castro (D-Texas), Julián Castro’s twin brother, tweeted a list of local Trump donors, the pair faced blowback from critics who accused them of dox'ing (all of the information was already public). As Julián Castro’s campaign manager, Rupert found herself caught in the crosshairs. She shared on Twitter that someone had found her personal cell phone number and texted her a “series of racist, misogynistic and anti-fat threats and insults.” Rupert hoped her honesty would give others a sense of the realities of working in politics.

“I'm writing this because the question I get asked the most often by young women of color who want to work in politics is how to handle moments like this,” Rupert tweeted. “Notice I didn't say they ask me whether things like this happen or whether, if they pursue their dreams of careers in politics, they will happen to them,” she continued. “They already know that answer.”

Rupert handled the moment as best she could. She changed her number and focused on the task at hand. “It sucks. It's scary. And what you do in that moment, is whatever you need to do to be able to survive and keep going because we have to do it,” Rupert tells Bustle. “There could not be a more important time for young women, for young women of color, for young black women to feel like they should be coming into this industry and shaking things up.”

For Rupert, part of that shake-up is about questioning the way campaigns have traditionally functioned. Under Rupert’s leadership, the Castro campaign was the first to announce that they would pay all interns. It wasn’t an easy choice. Castro wasn’t considered a top-tier candidate, and the organization was on a budget, but Rupert felt it was critical to the ethos of the culture she was trying to build.

"Being an expert in politics does not mean that you're going to know answers."

“When I was younger, one of the reasons I never worked in politics was because I could not afford to,” Rupert says. “I wouldn't imagine replicating it.”

That’s just one example illustrating how Rupert models a type of leadership that reflects who she is, while at the same time acknowledging just how complicated “authenticity” can be for women and people of color.

“By virtue of being very often the only black girl in school, in Girl Scouts, or whatever, there was this constant sense of ‘you're representing black people,’’ Rupert says of her upbringing. “As you get older, that turns into, 'I need to always seem very together and very polished.'” So Rupert decided it was incumbent upon her to offer another path forward. “If I kept replicating that, it would never stop,” she says.

As she navigates what it means for her to be the third black woman to run a presidential campaign, particularly when she is also working to elect the first Latinx president, Rupert relies on her sister, Imani, as well as a network of friends in other fields and other black women who are working on 2020 campaigns. “We're all unabashedly dedicated to our campaigns,” Rupert says, “but we also know what everybody else is going through and there is that willingness to have each other's backs.”

“I Get To Set The Tone”

Jen O'Malley Dillon with Beto O'Rourke. Courtesy of the O'Rourke campaign.

Even as 2020 campaigns continue to raise the bar on staff diversity, politics is still a business that as O’Malley Dillon describes it,has always been driven by men.” That manifests not just in numbers and titles, but in cultural norms. When she was younger, O’Malley Dillon recalls “putting on airs of toughness” to fit in. “You know, ‘I can hang with the guys’” she says. “‘Let me drink tons of beer’ so I can fit into a culture that was a really masculine power culture.’” Now, as part of her effort to shift that culture, she talks openly about rescheduling meetings so that she can take her children to school. “I get to set the tone,” she says.

Rupert believes that in order to continue to diversify the pool of presidential campaign managers, it needs to be a priority for candidates, one that is reflected both in their staffing choices and the support they offer their senior staff. It’s the type of support she feels she’s received from Castro.

“He doesn't treat me like he took a chance with me and hired a woman or hired a black woman. Probably because he trusts me and he values me,” Rupert says. “So I'm given that freedom and grace to grow into this job and make mistakes without feeling like this was an experiment and it failed.”

Most importantly, both Rupert and O’Malley Dillon hope that their examples will help reset expectations of what is possible, and who deserves a seat at the table.

“Everybody in D.C. thought that I was totally f*cking crazy,” O’Malley Dillon says. “I just felt like maybe someone could see this and be like, 'Oh actually you can live your life, balance a few things,' maybe not great sometimes and better on other days, and you can still campaign.” That, she argues, is critical to retaining top talent.

“If we don't have more women doing this and staying in it for a long time, we're not going to have the kind of levels of women running this stuff that we really should," O'Malley Dillon says.

And for women who are considering a career in politics, Rupert offers this: “Being an expert in politics does not mean that you're going to know answers. Sometimes you're guessing. It means that you have judgement. It means that you have common sense and it means that you know how to lead and work with a team. If you can do that, put yourself forward. You belong.”