A bright-colored illustration of a busy downtown street scene at nighttime, where a small group of Trump supporters in red caps are surrounded by Trump-protesting multicultural millennials. | Illustration by John Jay Cabuay

When Matt Mowers moved to Washington in November 2016, he wasn't expecting a hero's welcome. The young political operative had worked for Donald Trump's campaign in New York, where you can hardly walk down the block in many neighborhoods without spying the words "Fuck Trump" scrawled somewhere on the streetscape.

But last year, his new neighbors in Dupont Circle, the upscale area known for its stately townhouses and history as a hub of gay life in the District, pulled some moves that surprised even Mowers, by then chief of staff at the State Department's global AIDS office. In the run-up to Mowers' first Halloween here, one of his neighbors strung up a skeleton and a pumpkin next to each other on a tree. The pumpkin had a sign: "Now kids, just because you're orange doesn't mean you're related to him!" With the dangling skeleton was a more menacing note: "Donald Trump's EPA director."

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There's always tension when administrations change in Washington; a new cast of characters arrives, and an influx of appointees, lobbyists and hangers-on have to stake out their own ground. But the era of Donald Trump is—as in so many respects—different.

Washington is a hipper city now than it's ever been, a place where staffers, especially young staffers who want to drink and date and live normal millennial lives, would want to live. The problem is, if you work for Trump, it's also more hostile territory than it's ever been. The president campaigned against the very idea of "Washington," slammed cities as "war zones" and ran a racially charged campaign whose coded messages weren't lost on the diverse, Democratic-leaning residents of D.C.'s buzzing neighborhoods. The bar-filled areas that became synonymous with young Washington in the Obama era—Columbia Heights, Shaw, U Street, H Street—are full of anti-Trump T-shirts and street art. Even old Republican redoubts like Spring Valley in upper Northwest aren't very Trump-friendly.

So, what's a young Trumpie to do? Many still do live in D.C., and to understand what their lives here are like, we interviewed more than 30 millennial staffers from the Trump White House and across the administration, both current and former (many have already left), as well as a smattering of their friends and outside observers. Nearly all spoke on the condition of anonymity, to talk candidly about their personal lives or because they were not authorized by their bosses to comment. They told us their horror stories about being heckled on the street and their struggles to get a date. Unlike their predecessors, who made their mark on the city's social scene, they largely keep to themselves, more likely to hop between intimate apartment gatherings than to hit the town. "Instead of folks looking outward," explains one young White House aide, "more folks look inward."

Faced with open antagonism, Trump's millennials over the past year and a half have quietly settled on the margins: a stretch of Washington that spans from the Wharf—a shiny new development three blocks south of the National Mall—southeast along the Waterfront and into Navy Yard, on the banks of the Anacostia River. It's a string of neighborhoods that peer out over the water, separated from most of the city by an interstate, and facing away from official Washington. It's a bubble within the Washington bubble: Here, young Trump staffers mix largely with each other and enjoy the view from their rooftop pools, where they can feel far away from the District's locals and the rest of its political class.

It's not all a tale of discomfort. Many shrug off the drawbacks by pointing out that at least they're not in New York or back on their college campuses, where their politics were even less welcome. And they're learning one lesson that every new wave of operators learns: In Washington—even in Trump's Washington—as long as you have power, you can manage to feel popular somewhere.


It's a fact of social Washington—or it has been up to now—that each administration's junior staffers help to set the tone for D.C. "cool." In the Clinton years, the diverse and lively Adams Morgan—one of a small number of neighborhoods not far from the White House that was affordable and relatively safe in the 1990s—became a hub for young appointees. The arrival of President George W. Bush in 2001 brought a new generation of country club Republicans, and a Texas-Southern flavor, to the city. Bush's 20-something twin daughters and his youngest aides made the now-shuttered Georgetown bar Smith Point, where boat shoes and cocaine once abounded, and Glover Park's Town Hall into centers of the social scene. Young, diverse Obama staffers, meanwhile, were on the front lines of gentrifying historically black neighborhoods around U Street, Columbia Heights and Shaw, often preferring group houses where they lived with lots of roommates and threw raucous parties. Regular basketball games, especially Tuesday nights at an Interior Department court, were another hallmark.

The young Bush and Obama crews mustered a visible social presence in part because so many of them had bonded on the campaign trail; by the time they got to Washington, they were a crowd. But Trump's slapdash campaign was leaner, his team was thrown together on the fly, and it was riven by factions—meaning those staffers now in D.C. tend to keep a lower profile, in smaller groups. "With Trump, it's not like there's a huge contingent of New York people who came in. It's geographically very disparate," says a former Trump administration official. "They don't seem to be leaving the impact on D.C. culturally that Bushworld did."

An illustrated map of Washington, D.C., with color codes showing which neighborhoods were perceived as "cool" by the staffs of different presidential administrations. | Illustration by John Jay Cabuay

Illustration by John Jay Cabuay

Trump's young crew have, by and large, avoided the heart of the city. Their prime stomping grounds, from the Wharf to Navy Yard, is a swath of real estate at once more sterile than the vibrant urban neighborhoods preferred by their predecessors and more sightly, with clean new apartment towers and waterfront views. Trump staffers cluster in upscale buildings like Lex & Leo next to the Waterfront Metro stop and Navy Yard's One Hill South, which features two rooftop hot tubs and rents go as high as $3,000 a month for one-bedroom apartments. The president's two most famous millennial aides, senior adviser Stephen Miller and former communications director Hope Hicks, both took up residence at CityCenter, in the heart of downtown within walking distance of the White House, an area where many Washingtonians work but relatively few live; at the opulent mixed-use development, majority-owned by the government of Qatar and studded with luxury storefronts, a studio apartment rents for about $3,000 a month.

Unlike most of the rest of D.C., where gentrifying newcomers find themselves rubbing shoulders with lifelong Washingtonians, this Wharf-to-Navy-Yard stretch is mostly devoid of true locals—meaning young staffers living there are less likely to be bothered by unwelcoming neighbors. Instead, you'll find yuppies, tourists and affluent empty-nesters visiting from the suburbs. Stocked with brand-new boutiques and restaurants, as well as chains like Ben & Jerry's, the area imports the feel of a high-end northern Virginia shopping plaza to D.C. Snobbier millennials might call it "basic." In other words, it's right in the comfort zone for staffers who are unabashedly Republican but also carry chips on their shoulders about the elite insiders they beat out in 2016.

"It's not too ritzy," a 30-year-old administration ally says of the Wharf, where he recently brunched with three White House staffers at Kirwan's Irish Pub. "It's not, like, as ritzy as Georgetown."

When the Trump crowd ventures beyond those sprawling new apartment buildings, they tend toward eateries more upscale, conventional and close to work. The bar and steakhouse at the Trump International Hotel, of course, offer the most obvious safe space. Perhaps even more so than their predecessors, Trump's young staffers also rely on old standbys near the White House: POV, the rooftop bar at the W Hotel that overlooks the White House; Old Ebbitt Grill, a quintessential antebellum Washington establishment; and Joe's, a seafood and steak spot, are favorites. So are the nearby restaurant-bar The Hamilton and Blackfinn, a gastropub off Farragut Square. Some staffers prefer the Exchange Saloon, a no-frills sports bar just west of the White House. One young former Health and Human Services official confides that Rebellion, a Southern-themed establishment farther north, near U Street, is "one of the few closet Trump bars" in town.

Even before the era of ubiquitous cellphone cameras and viral social media scandal, young White House staffers sometimes stirred up trouble in public. After the 2008 election, photos emerged of Obama's young speechwriter Jon Favreau groping a cardboard cutout of Hillary Clinton; years later, he was caught on camera again, this time playing drinking games shirtless with fellow staffer Tommy Vietor at a barbecue joint in Georgetown. Trump staffers are perhaps wary of these risks. No one wants to end up like Hope Hicks and White House staff secretary Rob Porter, whom paparazzi caught on a date this past winter. The attention was soon followed by allegations of previous spousal abuse by Porter, who quickly resigned; Hicks departed Washington soon afterward. The caution starts high on the food chain: When the White House arranged for a focus group of four young staffers to sit down with us and sound off on their lives in Washington, we arrived to learn that the session would take place "on background," the ground rules more often used to brief reporters about sensitive matters of national security.

"There seems to be a lot of paranoia among people inside the White House that if they step out of line, that they will get their heads chopped off by the president's Twitter feed," says John Arundel, a magazine journalist and close observer of the Washington scene who says he has known Trump for 30 years. "They don't want to be seen as acting inappropriately or being seen out with the wrong person. They feel like they're targets."

There are outliers, however, who choose to make a statement on the social circuit. In April, for the second year in a row, Trump decided to ditch the annual White House Correspondents' Association dinner in favor of a rally, but he encouraged his staffers to hit the town in his absence. They did, wearing their Trump affiliation on their sleeve, in one case almost literally: Caroline Sunshine, a 22-year-old Disney Channel star turned White House press assistant, showed up at the dinner in a custom-made dress adorned with a collage of tweets and press coverage about her recent hiring at the White House.


It's not so surprising that Trump's young aides keep to themselves given the politics of the city they've colonized. Only 4 percent of the District's vote went to Trump in 2016; his next-worst showing was Hawaii, where he got nearly 30 percent of the vote. Trump's inauguration drew a lackluster crowd, and his real welcome to the city came the next day, when hundreds of thousands of protesters stormed the Mall for the Women's March. A constant stream of anti-Trump demonstrations has followed. Signs declaring "Love trumps hate" and other visible markers of the "resistance" are everywhere. Staffers leaving the White House grounds semi-regularly catch passersby flipping them the bird.

"I have gotten yelled at a few times walking out of work," lamented one White House staffer. "I want to get home, not get in a debate in the middle of Pennsylvania Avenue."

"Trump supporters swipe left"—meaning "don't even bother trying"—might be the single most common disclaimer on dating app profiles in Washington.

Sometimes, the easiest option is to hide their identities. While under normal circumstances, you could expect young White House officials to work their job titles into conversations at the earliest opportunity, the Trump crew has learned to use the types of dodges more commonly deployed by employees of the CIA. "I'll just say I work for the federal government," says a White House aide. After some conversations at bars on U Street and the Hill turned south when his Trump ties came up, one since-departed staffer has learned to reveal his White House past only as a last resort. "Even now, people have to ask five or six times before I say, 'Yeah, I worked there,'" he says. When being vague doesn't cut it, staffers can always straight-up lie, as one young administration official learned to do while working out of New York during the campaign. "I told people I was an auditor down on Wall Street, and people just stopped asking me questions after that," he recalls.

When it comes to disclosing their affiliation with Trump, no ground is more fraught than courtship. "Trump supporters swipe left"—meaning "don't even bother trying"—might be the single most common disclaimer on dating app profiles in Washington.

One beleaguered 31-year-old female administration official described at length her "very, very frequent" scraps with her matches on dating apps. "You do the small talk thing, and you have a very good conversation, and then they might say, 'You didn't vote for Trump, right?'" she says. "As soon as I say, 'Of course I did,' it just devolves into all-caps 'HOW COULD YOU BE SUCH A RACIST AND A BIGOT?' And 'You're going to take away your own birth control.'" In one recent star-crossed exchange, the official told a match she worked for the federal government. When he pushed, she revealed she was in the administration. He asked her, "Do you rip babies from their mothers and then send them to Mexico?"

Evasive answers will get you only so far, though, since many dating apps provide enough information for inquisitive users to sleuth out their matches' identities. "I literally got the other day, 'Thanks but no thanks. Just Googled you and it said you were a mouthpiece for the Trump administration. Go fuck yourself,'" says the official. It's all enough to drive her and some of her colleagues away from at least some of the apps. "I'm no longer on Bumble," she says.

Young staffers have had to develop a keen sense of just when to have "The Talk" with romantic partners. "I've still been able to hook up with women," says a male former White House staffer. "But I know that I need to be careful about broaching the Trump stuff. I just know that going in, I need to be able to get it out at the right time and not get it out too early to the point where it's like, 'Hey, I worked for Trump, you should stop talking to me,' but late enough in that eventually they know that there is this information floating out there that I worked for this guy and hopefully you have now seen that I'm not a horrible person and we can go further with this."

A cartoon shows six young women disgustedly fleeing a Trump-supporting young man in a red cap and bow tie. | Illustration by John Jay Cabuay

Another former Trump White House aide says the experience of his single colleagues has given him a new appreciation for life in a committed relationship. "Thank God I've had a girlfriend of three years," he says, "because the last person I would want to be is a single Trump supporter dating in D.C. right now." Yet another former aide put the best possible spin on the predicament. "My grandmother used to joke that the key to dating is to just be interesting, and I think working in President Trump's White House is the definition of interesting," he says.

A common coping mechanism is to date within the administration, or go on intra-administration double dates. "Other couples often want to do double dates with Vanessa and I," says Mike Ambrosini, 27, who served last year as special assistant to the president and director of the office of the chief of staff; his fiancée, Vanessa Morrone, also 27, is White House director of regional communications. Other Trump couples in the mix for the outings include Madeleine Westerhout, Trump's executive assistant, and her boyfriend, Ben Schramm, a political appointee at the Pentagon and a former Marine social aide at the White House, as well as Giovanna Coia, a White House press assistant, and her boyfriend, John Pence, a senior adviser on Trump's reelection campaign. Coia is also the cousin of White House adviser Kellyanne Conway, and Pence's uncle, of course, is the vice president.


If there's one thing young Trump staffers share with the legions of young political animals who came before them, it's career ambition, and a willingness to put up with a lot to enjoy the fruits of their positions. The social ostracism that millennials in this administration face might be unique, but for the most part it's just one more inconvenience to endure, along with long hours and relatively low pay.

For all the hostility and awkward Tinder conversations, they told us, Washington still has no shortage of people drawn to prestige. "At the end of the day, if they are part of the establishment and living in D.C., they usually want or need something from the White House, which can be kind of nice," says one Trump staffer. "It's a powerful building," says another. "People respect it." A junior administration official said some of his neighbors near the H Street corridor discovered he worked at the White House after seeing him on television; even they thought it was cool.

Besides, if you're a young conservative, there are worse places to be than Washington. "Being a Republican at college was actually more difficult," according to one young White House staffer who attended a large Midwestern state school. "People have been more hostile in New York," adds a young veteran of the Trump campaign who moved down to Washington to work in the administration. "If you're wearing a Trump jacket in New York, you're going to get catcalls and stuff like that."

As a former Trump appointee explains, her young peers in the administration are old enough to know that, as divisive as American politics is at this moment, some things about the capital never change. "They don't care that people are hostile to Trump," she says. "They still have some semblance of power and access, the things that matter in D.C."

Daniel Lippman is a reporter at Politico and co-author of Politico Playbook.

Ben Schreckinger is a national political correspondent at Politico.