Co-host of the War Room podcast Natalie Winters ’19 stood just offstage in Rugby Auditorium as the heat of the lights spilled over the crowd and the low hum of student voices buzzed like static. She had expected to see a handful of kids, maybe a bored teacher or two. Instead, the auditorium overflowed with chatter as students packed the seats, lined the walls and spilled into a secondary viewing room set up to accommodate the turnout. Winters approached the mic. She spoke sharply, challenging mainstream feminist narratives. Gasps cut through the room, and footsteps echoed as someone walked out of the auditorium. Although not the most positive high school memory, Winters said the moment was transformative because the school gave her a platform to express her views even when some did not agree with her.
“That was when I realized people like watching these debates,” Winters said. “It was a very eye-opening moment because sometimes liberals who never [accept] my views are unfairly impugned as being very ossified in their ideology. [They] get very offended by hearing different viewpoints. That’s why I appreciated going to Harvard-Westlake because it taught me how to cater my message and my arguments to people who I knew did not agree with me. I use those skills now on TV, but instead of being broadcast in an auditorium, we’re getting a million-plus views and are shared by the president and his advisors.”
The school’s alumni have gone on to politics across the ideological spectrum, with many working behind the scenes for campaigns or working in the media. Former Los Angeles Mayor and current U.S. Ambassador to India Eric Garcetti ’88 and former U.S. Attorney and Special Counsel Robert Hur ’91, attended the school. Hur is currently representing Harvard University in its confrontation over federal funding with the Trump Administration, according to Politico.
After graduating from Macalester College, Emma Kaplan ’08 said she got involved in politics by working under Former Speaker of the House Nancy Pelosi, who taught her about the nuances of politics and change-making.
“I got a job working for Nancy Pelosi, who, at that point, was the [House] Minority Leader,” Kaplan said. “I got this amazing close-up view of how you make change, and it wasn’t how I thought it was. I thought it was this lofty thing. [I thought] we had this vision and we’re going to get there by pushing forward, convincing everybody that this is the right way to do it. Instead, it’s very person-to-person. You have to convince people to get on board by knowing who they are and what makes them tick. Sometimes I manipulate situations in a good way, creating situations that can better get the thing you want to do across the board. Sometimes it works, sometimes it doesn’t, but when it does you can see real change and sometimes really substantial change.”
At 24 years old, Winters has served as the White House correspondent for the War Room podcast since January 28. She reports for Steve Bannon’s “War Room” podcast, which reaches a wide Republican audience, including top government officials and the president, according to the New York Times. Winters said she first got involved in the podcast as an intern. She then became a co-host and during Bannon’s time in prison, she stepped in as the sole host.
“I started flying back and forth more or less every week from DC to Chicago,” Winters said. “Then at the emergence of the first Trump impeachment, Bannon got back together to start the show that ultimately turned into the show I now co-host and hosted while Steve Bannon was in prison. I started working behind the scenes as a staff writer, and embraced the Harvard-Westlake hard-work mentality. Ultimately, I worked my way up to becoming Steve’s co-host at the age of 20. I started appearing on conservative media and broke a lot of stories.”
While Winters found her voice through the media, voicing her opinions proudly, Kaplan was inspired by a moment of national unity as a campaign unfolded during her senior year. Kaplan said participating in a rally during the Obama campaign was a significant memory from high school.
“When I was a senior at Harvard-Westlake, it was 2008,” Kaplan said. “It was the first year that Obama ran, and young people across the nation became super excited by his run, who he was and what he stood for. [I have] this vivid memory of skipping Peer Support on a Monday to go to Obama’s rally in Los Angeles.”
Like Kaplan, Luke Rascoff ’27 said he is getting involved in campaigns while still in high school.
“Politics has an incredibly tangible impact on people’s lives and the legislation that gets passed is something that people should be paying more attention to,” Rascoff said. “I’ve gotten involved by volunteering on political campaigns, a congressional campaign over the summer and, most recently, the Kamala Harris campaign in Pennsylvania in October.”
For individuals like Kaplan and Rascoff, political identities can develop through campaigning. However, in Winters’ experience, they can develop through a willingness to express political opinions even when her audience disagrees.
“I had an English teacher, and I thought she was one of the most wonderful teachers I had,” Winters said. “I loved the analysis of poetry [and] literary devices, but she was very left-wing and shared her political ideology with the class. I felt the need to sort of pretend to get along, but I didn’t like lying about my beliefs. Eventually, I outed myself as supporting Trump, but it was an oddly cathartic experience. From a psychological level, I just decided, from that moment forward, I would never lie about my political beliefs just to appease people.”
Both Winters and Kaplan reflect on their experiences in high school as formative and impactful on their careers. Kaplan said her experience as a prefect and participation on the Honor Board shaped her political aspirations.
“The Honor Board truly was this eye-opening experience for me,” Kaplan said. “It sounds corny as a 34-year-old person to say that, but it truly was a game changer for me. It made me think about the ways that we make decisions about other people’s lives, what we prioritize and what we include in the Honor Code. The things that grounded Harvard-Westlake as an institution translated into what I do and what I’ve been doing since I graduated from college.”
Former Georgia Press Secretary for Harris for President, Alice Nam ’16 said she found herself working closely with some of the country’s top Democratic leaders. Nam said working on political campaigns and gaining experience is incredibly valuable to her.
“I interned in Speaker Pelosi’s office in the beginning of 2020, and then in the spring of 2020, I ended up getting a job in Senator Chuck Schumer’s office,” Nam said. “I never looked back. I worked on his upstate press team and his national press team. I helped write guidance for Senate Democrats and went on to be Representative Marilyn Strickland’s communications director. I was Senator [Laphonza] Butler’s deputy communications director while she was in the Senate. In April of last year, I joined the then Biden-Harris campaign that transitioned into the Harris-Walz campaign.”
Nam said she used her voice to elevate underrepresented communities within progressive campaigns. She said one of her most rewarding moments in her political journey was her experience as the Georgia Press Secretary for the Harris campaign because she was able to give a voice to the Asian American community.
“To see people and their struggles, to acknowledge them and then to be able to help elevate them to a public or more national stage has been one of the most rewarding parts,” Nam said. “That is why I continue to want to do [this work]. Moments when you [are] not just working for a specific presidential candidate, but [are] able to hear people’s struggles is one of the privileges of [doing] political work. I bear witness to people’s struggles and triumphs and share those with the rest of the world.”
On a personal level, Kaplan said one of her most memorable career moments was working on and helping plan the joint session of Congress when Ukrainian President Volodymyr Zelenskyy spoke to Congress.
“I got to be there for it and see him walk onto the floor and address the House, the Senate and the diplomatic corps with such conviction about what’s happening in Ukraine and the help they need from this country,” Kaplan said. “That moment will stick with me forever.”
A 2023 study found that 63% of women said there are too few women in high political positions in the US, according to the Pew Research Center. Winters said she does not view her gender as a limitation although she works in a male dominated field.
“It would [have] made me scared that being a young girl in the professional world was going to be held against me, but I think it’s been one of the biggest blessings in my career,” Winters said. “It was that way because I’ve never used being a woman to get ahead. Many people like to talk about feminism, and I never really did that. I just did real, raw reporting, like a Harvard-Westlake English essay on steroids. I didn’t make it my brand or my personality, but now I maybe play into it a little more but only because the left media has made it a thing.”
Although Winters said she is proud of her accomplishments at a young age, she has also faced criticism. Winters said she received negative comments about her wardrobe from news outlets.
“If you search my name and Daily Mail, there was a huge scandal,” Winters said. “They did not like what I wore in the White House and sort of mocked me saying I was the White House correspondent famed for wearing skimpy outfits. I was wearing the most blasé sweater. I only get [criticism like that] from the media. I would think that’s maybe the most transformational shift from starting at the White House. I used to be more contained [within] the MAGA news sphere, [which] was a little more esoteric, as opposed to [being in the] general international media. That comes with doing more shows. I do Piers Morgan a ton. I just did interviews [with] The New York Times and CNN. I think they only use the what-I-wear comments to impugn my reporting, which ironically is coming from the left.”
Gen Z is a dominant force in the electorate, but many young voters express a sense of fatalism about the political system’s ability to address these challenges, according to University of California, Berkeley Research.
The alumni have made their impact on national politics, Rascoff said he wishes students of his generation were more involved in politics and got more informed about issues.
“I wish that there was more discussion of politics by students at Harvard-Westlake,” Rascoff said. “It seems like something that people are not as excited to talk about. I am more liberal, and I support Democrats, but I hope that no matter what political affiliation someone has or what their interest in politics is, they feel comfortable discussing it with their teachers [and] with their fellow classmates in as many settings as possible because I think the more students discuss politics, the more engaged they are and the more young people we have in the political system, the more positive change we’re going to produce. Right now, it feels like everyone’s kind of scared to talk or say the wrong thing. [It] doesn’t feel like they’re informed enough. I wish people jumped in more.”
When reflecting on her experiences throughout her political journey, Kaplan said she recalls both positive and negative moments.
“I’ve gotten to be a part of once-in-a-lifetime experiences, some of them amazing and some of them truly tragic,” Kaplan said. “I was there on January 6 and I was there when we had a unified Democratic government. We were able to pass such significant legislation, like the Inflation Reduction Act, the Build Back Better infrastructure bill and the Tips and Science Act. We passed the PACT Act, which protects veterans who have experienced burn pits and provides them with healthcare. Legislation big and small made a difference in so many people’s lives. Getting to be a part of two impeachments was also kind of wild to me personally. I’ll just never forget that.”
