‘HE WAS LOOK­ING FOR HOW TO BE, IN KIND OF A PURE WAY’

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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 whoshould-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 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 1 Per­cent — 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, 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, 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 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, O’rourke was pay­ing $130 a month to share a 2,000-square­foot loft with cre­ative types in Wil­liams­burg, Brook­lyn. (Down­sides of the bar­gain in­cluded DIY bed­room con­struc­tion and in­door tem­per­a­tures so low that ten­ants could see their own breath.)

For 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.

“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, 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, Wil­liams, who had tapped into New York’s mu­sic scene. Be­fore that, 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 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,” 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, 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 O’rourke’s fa­vorite groups.

He of­ten kept a mu­si­cian’s rol­lick­ing hours — “He liked to drink beer,” 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 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?”

For a time, 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 DriveIn and the Mars Volta.

But as he pre­pared to leave col­lege, his hair now shorn a bit, 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 Wat­son, his girl­friend at the time, de­spite not be­ing en­rolled.

“He was sort of seek­ing,” 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. 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 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,” 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,” O’rourke said. “You don’t know how to con­nect again.”

A chance re­union with a col­lege friend at a bar in Wil­liams­burg landed 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, 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.

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, 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. 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,” 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 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 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,” Wat­son said.

The New York dream was punc­tured for good, like many be­fore and since, on the rails of the Metropoli­tan Trans­porta­tion Author­ity. 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.’ ”

O’rourke bought a truck on Long Is­land for $1,000 and packed his New York life away. He said his good­byes and drove.

KATHY WIL­LENS / AS­SO­CI­ATED PRESS

Beto O’rourke, left, ap­pears with Oprah Win­frey for “Oprah’s Su­per­soul Con­ver­sa­tions from Times Square” on Feb. 5 in New York.

TODD HEISLER / NEW YORK TIMES FILE (2018)

Beto O’rourke greets Nov. 6 vot­ers out­side of a polling place in El Paso, Texas. Dur­ing his time in New York, O’rourke de­vel­oped a re­pu­a­tion as a so­cially dex­trous Texan who could talk to any­one.

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