All at once, New York City seemed to be conspiring against Beto O’Rourke.
His girlfriend was moving to France. His punk bandmates had scattered. Twenty-three and searching — with an Ivy League degree that could not pay rent — Mr. O’Rourke subsisted as a live-in nanny on the Upper West Side, with a futon in the maid’s quarters, watching over a wealthy family’s two preschoolers.
“I just remember his dad coming,” said the former girlfriend, Sasha Watson, recalling a pep talk from Pat O’Rourke, a prominent Texas county commissioner and judge, who insisted his son was destined for “bigger things.”
“He really saw great things for Beto.”
Great things were not happening. By late 1995, Mr. O’Rourke had fallen into the deepest depression he can remember. He worked for an uncle’s tech business because it was a job. He spent nights alone listening to his cassettes because it passed the time.
“Little bit of a sad case,” Mr. O’Rourke said.
More than two decades later, long after what friends describe as a quarter-life crisis, Mr. O’Rourke has arrived at a midlife crossroads of enormous consequence, with revealing parallels to his time in New York. Forty-six and searching — after a narrow Senate loss in Texas last year that propelled the former El Paso congressman to Democratic stardom — he has been driving around the country, alone, introducing himself to strangers, deciding if he wants to run for president.
He has described himself as “stuck,” in and out of a “funk.” He has compared the present reckoning to moments of rootlessness in the city, when he last found himself out of work.
“I just didn’t ever want to feel like that or be in that place or that position again,” Mr. O’Rourke said in an hourlong phone interview. “So that lately has felt kind of strange, maybe with some echoes.”
Early polls and prospective opponents agree that Mr. O’Rourke, with his message of generational change and liberal-for-Texas politics, would enter the race as a top-tier contender, buoyed by a national network of small-dollar donors and an instinct for uplift and social media ubiquity.
Well before his return this week to his former city — for an interview on Tuesday with Oprah Winfrey in Times Square, heightening 2020 expectations — Mr. O’Rourke’s New York chapter has stood as the unlikely forerunner to his political rise, laying bare the unusual path that led him to national politics and the who-should-I-be self-reflection that has come to define his presidential deliberations.
Then, as now, he appeared less concerned with political ideology than the pursuit of authentic experiences and a sense of community, an instinct that has frustrated some progressive voters who question Mr. O’Rourke’s policy convictions. Then, as now, he could swerve quickly from mawkish to mischievous — by turns a goofy extrovert and a lone wolf, withdrawing in moments of introspection.
If there is a certain kind of New York story that successful people tell about themselves — the tenacious artists, grinding until they get discovered; the downtown capitalists, rat-racing into the One Percent — Mr. O’Rourke’s is not one of those.
While past political figures, most memorably a young Barack Obama, found their intellectual moorings among the city’s thinkers and strivers, Mr. O’Rourke’s seven New York years (four at Columbia University and three after graduation) were, in his own telling, often an exercise in recognizing his own averageness. He loved music but came to see he was not talented enough to hit it big. He thought he might pursue publishing but struggled to break in. He was intimidated by the intelligence of his peers.
“He didn’t really have the kind of ambition that a lot of people have in New York,” said Brooks Williams, Mr. O’Rourke’s uncle, who has lived and worked for decades on Franklin Street. “It wasn’t fulfilling for him.”
Yet New York also supplied an early proving ground for the kind of personal appeal that would power Mr. O’Rourke’s ascent, showcasing a gift for gab and whimsy and binding him to a circle of friends who remain confidants.
At the age when many would-be presidential rivals had long since chosen their course, zipping through law school and storming into politics, Mr. O’Rourke was paying $130 a month to share a 2,000-square-foot loft with creative types in Williamsburg, Brooklyn. (Downsides of the bargain included D.I.Y. bedroom construction and indoor temperatures so low that tenants could see their own breath.)
For Mr. O’Rourke, the period was an early lesson in his own limitations. “I’m not great solo,” he said. “I need people.”
For those who knew him, another observation now comes to mind: They did not believe they were looking at a future statesman.
Mr. O’Rourke in the late 1990s with his ex-girlfriend, Sasha Watson, in New York. “He was sort of seeking,” Ms. Watson said. “He was looking for how to be, in kind of a pure way.”
“You’re supposed to make friends with future secretaries of state, not weirdo musicians,” a friend, Adam Mortimer, said. “It’s like, wait, one of the weirdo musicians might run for president.”
The rollicking music years
He seemed like any other punk-minded student: Jawbox T-shirt, hair past his shoulders and a grim insistence that the Smashing Pumpkins had grown pretentious.
By college, friends say, Mr. O’Rourke had settled on the outlines of an identity that would last: a rebel in moderation, more puckish than unruly. He said he chose Columbia in part because of the financial aid package and in part because he looked up to his bohemian uncle, Mr. Williams, who had tapped into New York’s music scene. Before that, Mr. O’Rourke had attended boarding school in Virginia, largely to create some distance from his father, a political obsessive who did not understand his son’s musical leanings.
Now Mr. O’Rourke had the run of the city. He went by Robert — Beto was a nickname from El Paso, owing to its border-town bilingualism — and he played the guitar, establishing himself as the school’s gentle punk rocker.
When a bandmate in a group called Swipe adopted a belligerent performance persona, telling crowds that they were listening to “Angry Swipe,” Mr. O’Rourke protested from the stage. “He was like, ‘No, we’re not. We’re not angry,’” the band member, Alan Wieder, said. “It made him very uncomfortable that I was mean.”
Offstage, Mr. O’Rourke was a prolific dabbler, straddling disparate orbits. He was socially conscious but not especially political, “other than whatever kind of politics were being talked about in Fugazi,” a former roommate, Jeff Ryan, said, naming one of Mr. O’Rourke’s favorite groups.
He often kept a musician’s rollicking hours — “He liked to drink beer,” Mr. Wieder said, “not in the Brett Kavanaugh sense” — but also rowed crew, requiring him to rise by 4 a.m. for practice on the Harlem River. He was an English major skilled enough with computers to introduce roommates to the culture of early-1990s chat rooms, once pranking a girlfriend by posing as a romantically interested woman online.
“I kind of have a boyfriend,” the girlfriend, Katherine Raymond, recalled typing back to the person she did not know was Mr. O’Rourke, as he sat in an adjacent room. Then she heard a shout through the wall: “What do you mean you kind of have a boyfriend?”
The cover, left, and back cover, right, of “The El Paso Pussycats,” an EP by Foss that featured Mr. O’Rourke, left, with Arlo Klahr and Mike Stevens.
For a time, Mr. O’Rourke still thought that music might provide a long-term plan. Friends from El Paso, with whom he had toured, seemed committed to trying. One of them, Cedric Bixler-Zavala, later headlined successful groups like At the Drive-In and the Mars Volta.
But as he prepared to leave college, his hair now shorn a bit, Mr. O’Rourke seemed to accept that music would become more passion than profession. He took writing workshops. He read Greek tragedies (“the Greeks got me, man”). He attended astronomy class with Ms. Watson, his girlfriend at the time, despite not being enrolled.
“He was sort of seeking,” Ms. Watson said. “He was looking for how to be, in kind of a pure way.”
She remembered a professor asking once what students wanted from life. Mr. O’Rourke said he hoped to be “a simple man.”
“That,” the teacher said, “is not a simple thing.”
A Texan in Williamsburg
The nanny life was perhaps too simple for Mr. O’Rourke.
High above Manhattan, in the historic Apthorp building at 79th and Broadway, he would wake to make breakfast for the family’s young son, help him dress and walk him to school. “Another nanny,” Mr. O’Rourke said, “came in for the little girl.”
Still working during the day for his uncle, he left the caretaking job after a few months and answered an ad in The Village Voice to rent a room in a small Brooklyn apartment alongside a couple recently emigrated from the Ivory Coast. Loneliness consumed him.
“You kind of feel sorry for yourself,” Mr. O’Rourke said. “You don’t know how to connect again.”
A chance reunion with a college friend at a bar in Williamsburg landed Mr. O’Rourke a share of a not-yet-livable loft area on Wallabout Street. The group essentially constructed the interior from scratch, clearing mounds of debris and erecting walls. Guitars and drums soon filled the space. A cat named Dot paced among the record collections. Someone scrawled an apartment motto in a bathroom rich with graffiti: “It’s not a lot, Dot, but it’s what we’ve got.”
In a neighborhood of Hasidic Jews, Mexican-Americans and residents from the Marcy Houses blocks away, Mr. O’Rourke developed a reputation as the socially dexterous Texan who could talk to anyone. “If you needed somebody to talk to somebody, you asked Beto,” a neighbor, Yuval Adler, recalled.
Mr. O’Rourke grew so close to the building superintendent that the man gave the group a premium toilet, albeit with a cracked seat cover.
“He would come to the building in the morning and just stand outside and scream, ‘Robert! Robert!’” a roommate, David Guinn, said of the super. “It would be like 6:30 in the morning.”
In other moments, apartment security was found wanting. Amid a celebration after building a new room, Mr. O’Rourke noticed something strange through the window. “We were drinking a beer in the room that we had just built,” he said. “I was like, ‘Hey, Dave, that guy’s riding a bike that looks a lot like your bike. And he’s carrying a word processor that looks a lot like yours, Mike.’”
They had been robbed as they sat in their own apartment.
Most memories were happier ones. Live music pounded until dawn. Housemates gathered on a rooftop trampoline, recovered from the set of a Busta Rhymes music video, to watch the sun sail past the Twin Towers. Mr. O’Rourke found work moving fine art for a company called Hedley’s Humpers — a Picasso here, a samurai sword there — and the apartment remained a neighborhood hub for creativity and mind-calming indulgence.
“Pot, yeah, there was definitely, you know,” Mr. O’Rourke said. “There was, uh, I don’t know how to put this, but yeah. People smoked pot, but not habitually.” (He allowed that he was among those people.)
Yet Mr. O’Rourke never felt like a permanent New Yorker, he said. No job fit quite right; no prospect particularly appealed.
His father’s hopes, friends say, loomed as subtext, even if Mr. O’Rourke seemed intent on making his own choices.
“Pursuing a life so different from Pat’s — an artist’s life — and fearing that his father would not understand, that was hard for him,” Ms. Watson said.
The New York dream was punctured for good, like many before and since, on the rails of the Metropolitan Transportation Authority. Mr. O’Rourke was commuting to the Bronx for an entry-level publishing job, “smashed up against the glass” of a packed subway car.
He thought about El Paso open spaces, El Paso food, El Paso family.
“I just had this vision of being in my truck with the windows down,” he said. “I remember calling my folks that night, and I said, ‘Hey, I think I’m going to come back.’”
Mr. O’Rourke bought a truck on Long Island for $1,000 and packed his New York life away. He said his goodbyes and drove.