AMES, Iowa—The presidential run of Beto O’Rourke is a profoundly personality-driven exercise, his charisma and Kennedy-esque demeanor the topic of one profile after another, so it’s surprising to listen to his speeches on the stump in which he doesn’t talk a whole lot about himself. In Iowa recently, over several days in a rainy, foggy, uncertain stretch of spring, O’Rourke delivered a series of speeches and held question-and-answer sessions in which he spoke at length about unity, civility and inclusivity, and only rarely touched on his personal story. There was one notable exception: When he did offer up bits of his biography, he leaned most heavily on his run last year against Ted Cruz for a spot in the United States Senate.

He recounted for the crowds tales of the places he went and the people he met during his barnstorming, freewheeling, attention-getting campaign, coming back to two numbers: 254, the number of counties in gargantuan Texas, all of which he visited … and the percentage-point margin by which he was defeated.

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“We lost by 2.6 percent,” he said in a basement music venue here at Iowa State University.

“We lost that Senate race in Texas by 2.6 percent,” he said in a downtown greasy spoon in Storm Lake.

“We came within 2.6 percentage points of defeating Ted Cruz,” he said in a community college cafeteria in Fort Dodge.

“So close,” the local party leader said in introducing O’Rourke one morning at a brewpub in Carroll. “So close.”

The part of his past that he talked about the most, by far, was a race that he lost.

O’Rourke, 46, campaigns with the wanderlust of the wannabe punk rocker he once was and the vigor of the regular runner, hiker and cyclist he still is. His hair is somehow simultaneously boyish and salt-and-pepper-streaked. He drives himself around in rented Dodge minivans, dressed almost always in plain brown shoes, Banana Republic chinos and blue oxford shirts with no tie and the sleeves rolled up just so. He often dons locally appropriate dad hats, from a maroon Iowa State cap at Iowa State to an orange Clemson cap at Clemson and so on. He holds microphones with his right hand kind of like a singer, and he extends his left arm into the air kind of like a preacher, and he punctuates his points with grins that flash perfectly imperfect teeth.

After Iowa, I dropped in on O’Rourke on the trail in South Carolina and Virginia, listening to him rat-a-tat-tat through his airy, often alliterative talking points about “common cause” and “common ground” and “common good” and “conscientious capitalism” and “our aspirations” and “our ambitions” instead of the “pettiness” and the “partisanship” of politics today, along with planks of a nascent platform like a new voting rights act, citizenship for Dreamers, “world-class public education” and “guaranteed, high-quality, universal health care.” And almost always, when he did talk about himself, it would be back to the time he fell just short. “We lost by 2.6 percent,” he said to a small, low-key gathering in rural Denmark, South Carolina.

Celebrating defeat is unusual for a politician, and doing so makes O’Rourke notably different from the rest of the unwieldy field of Democrats running for president. In contrast to the 20 or so other 2020 candidates—all of them in various ways overachievers who tout the litanies of their successes—O’Rourke instead presents his loss to Cruz as a prominent selling point. More than his ownership of a small business. More than his six years on the city council in his native El Paso. More than his next six years as a back-bench House member in Congress. His near-miss against a prominent Republican in a red state was such a high-quality failure, so epically heroic, he seems to suggest, that it should be considered something of a victory. And he’s not wrong to do it. His failed Senate bid, after all, is singularly what made him famous, what got him an interview with Oprah, what put him on the cover of Vanity Fair—and what’s put him in the top handful of aspirants angling for a shot to topple President Donald Trump.

But while it might be his most spotlit miss, it’s not an aberration.

There’s a reason his biography doesn’t feature much in the campaign. For O’Rourke, the phenomenon on display in that race—failure without negative effects, and with perhaps even some kind of personal boost—is a feature of his life and career. That biography is marked as much by meandering, missteps and moments of melancholic searching as by résumé-boosting victories and honors. A graduate of an eastern prep school and an Ivy League rower and English major, the only son of a gregarious attorney and glad-handing pol and the proprietor of an upscale furniture store, the beneficiary of his family’s expansive social, business and political contacts, O’Rourke has ambled past a pair of arrests, designed websites for El Paso’s who’s who, launched short-lived publishing projects, self-term-limited his largely unremarkable tenure on Capitol Hill, shunned the advice of pollsters and consultants and penned overwrought, solipsistic Medium missives, enjoying the latitude afforded by the cushion of an upper-middle-class upbringing that is only amplified by his marriage to the daughter of one of the region’s richest men.

“With a charmed life like his, you can never really lose,” an ad commissioned by the conservative Club for Growth sneered last month. “That’s why Beto’s running for president—because he can.”

“A life of privilege,” David McIntosh, the president of the Club for Growth, told me.

It’s not just Republicans who think this. “He’s a rich, straight, white dude who, you know, married into what should politely be called ‘fuck you money,’” Sonia Van Meter, an Austin-based Democratic consultant and self-described “raging feminist,” told me. “His biggest success is by definition a failure,” she added. “He’s absolutely failed up.”

Even by the experience-light standards of the most recent occupants of the White House—a first-term senator followed by a real estate scion and reality TV star—the notion of O’Rourke’s uneven résumé blazing a path to the presidency is new and remarkable. For the moment, he is trailing and slipping in the polls, but it’s early, and he is still attracting besotted fans. The support O’Rourke built that even allowed this run in the first place did not depend on traditional concepts of meritocracy and diligent preparation. To look deeper into his past, to talk to his friends from his teens and his 20s, to read distant clips from money-losing media ventures, and to talk to voters, too, is to see a different kind of claim to excellence. In the end, O’Rourke’s best recommendation that he can win might be that he knows how to fail big—and then aim even higher.

O’Rourke’s ascent in some sense started more than 20 years back. In the summer of 1998, he made the choice to quit New York. He had graduated in 1995 from Columbia University, then spent most of the next three years playing, listening to and talking about music, reading the Economist and the New Yorker, drinking Budweiser, riding in cramped subway cars. He had worked for short periods as a nanny, a copy editor, a hired-hand mover of art and antiques, and in a series of odd jobs around the city that let him split cheap rent in a sparsely furnished Brooklyn loft where he liked to jump on a rooftop trampoline. Now, though, he wanted out, and so he bought a used pickup and drove home, steering toward more open road. He was, he has said, “young” and “happy” and “carefree.”

This decision to leave New York, his longtime friend Lisa Degliantoni told me recently, was and remains O’Rourke’s biggest, most consequential accomplishment—not just a learning experience or a tail-between-his-legs withdrawal, she believes, but an accomplishment. In her mind, it unleashed O’Rourke, allowing him to be “transformational”—first for his city, then for his state, and now potentially for his country.

Trading the bright lights and the bustle for the relative ease and isolation of the desert by the Mexican border, Degliantoni said, was risky, “because as soon as you’re there, you’re off all the radars.” That risk was mitigated significantly, however, by what he was heading home to, according to interviews with nearly two dozen people who have known him or worked with O’Rourke. Riding shotgun in the cab of that pickup was Mike Stevens, another one of his best friends, and when they logged the last of those 2,200 or so miles, Stevens told me, waiting for O’Rourke in El Paso was far from certain success but also “a pretty large safety net.”

He used it. Upon his return, he worked at first in the warehouse of his mother’s store. That fall, he was arrested after driving drunk in his Volvo at 3 a.m. and sideswiping a truck at “a high rate of speed” on Interstate 10. He went to “DWI school,” finishing the next spring.

It was his second arrest. Three years before, he had been apprehended by the police at the University of Texas El Paso after tripping an alarm trying to sneak under a fence at the campus physical plant while “horsing around” with friends. Prosecutors didn’t pursue the charge. (“No consequences,” said McIntosh from the Club for Growth.)

The next year, in 1999, O’Rourke started the Stanton Street Technology Group, an offshoot of which was StantonStreet.com. The website covered the arts and food and local politics and endeavored to be “the most comprehensive, interactive, and entertaining home page in the Southwest.” In the summer of 2000, it was registering 32,000 monthly “impressions,” according to O’Rourke at the time, a figure whose impact is hard to gauge given the early era of the internet and the size of El Paso—but the site also was bleeding money, taking from the coffers of the web design business. Even so, in January 2002, he launched a weekly print version. Bob Moore, the former editor of the El Paso Times, told me he used to rib O’Rourke that one of his few advertisers was his mother—“his only advertiser,” he said, “for the longest time.” It lasted 15 issues.

The newspaper was, said Degliantoni, who worked on it with him, O’Rourke’s “love letter to his hometown” but also “probably in hindsight not the best move.” Even O’Rourke joked about it recently in his remarks in Storm Lake. “In a brilliant stroke of genius, just as print newspapers were in decline,” he told the standing room only, shoulder to shoulder, coffee shop throng, “I started a print newspaper.”

The result? “We bankrupted the operation,” O’Rourke said to what sounded like good-natured, forgiving titters.

No matter.

He had run the website and started the paper “to be as engaged as I possibly could,” he later explained. “The logical conclusion,” he continued, “was to run for office.”

He ran for City Council in 2005 and won, and won again in 2007, backed by El Paso’s business elite, and then he ran for Congress in 2012, challenging in the primary Silvestre “Silver” Reyes, an eight-term incumbent who would have the endorsements of a pair of presidents (Bill Clinton and Barack Obama) and never before had had even a close call in a reelection. It was, political analysts in the area agreed at the time, a bid that smacked of audacity and risk. “It’s close to impossible to get a sitting member of Congress out of office because of the privilege and power,” O’Rourke said early on in his campaign.

But O’Rourke, of course, had a share of both as well, hailing from “an old El Paso political family,” as a local columnist pointed out, calling O’Rourke “just as ‘household’ around here as the stately congressman himself.” A company owned by his father-in-law, the real estate tycoon Bill Sanders—he’s worth at least an estimated half a billion dollars—gave $18,750 to a PAC that supported O’Rourke’s campaign. Reyes threw around the words “family wealth” and charged that O’Rourke was “a show pony” and “part of the 1 percent.”

In the end, though, painting Reyes as an aging Washington insider, and employing block-by-block door knocking, O’Rourke won with 50.5 percent of the vote.

Friends and admirers say O’Rourke is nothing if not a hard worker, wearing out shoes and racking up miles. “I think he’s the hardest-working man in U.S. politics,” said Steve Kling, a Democrat who lost last year running for the Texas state Senate. They describe him as an exceptional listener.

In his three terms in Washington, O’Rourke compiled a moderate to centrist voting record, which in this left-leaning primary could become problematic. He was known in D.C. as sufficiently affable but also something of a loner, say Capitol Hill staffers, a floating, unthreatening member who had undercut his clout by pledging to stay no more than four terms.

When he began his race against Cruz, it’s easy to forget, O’Rourke was close to unknown—even in Texas. Cruz, on the other hand, was one of the most prominent Republicans in the nation, and no Democrat had won a statewide campaign since 1994. Texas Senator and Majority Whip John Cornyn dubbed it “a suicide mission.”

But what, strategists and operatives say now, did O’Rourke really have to lose? He had engineered his own congressional exit, anyway, 2018 was shaping up to be a favorable year for Democrats, and Cruz was a legendarily unpopular foil against whom he could rally support. And the worst-case scenario? Something O’Rourke had done before. Just go home. Go back to El Paso. Failure, in fact, was an option.

“Beto,” Southern Methodist University political scientist Cal Jillson told Texas Monthly in March 2017, “lives life with a cushy net beneath him.”

“It wasn’t that big of a risk,” Texas-based GOP strategist Brendan Steinhauser told me.

The biggest risk he took in the Senate bid, in the estimation of politicos in Texas and beyond, was to listen to people who lived in all 254 of the counties in Texas more than he did to people who could have armed with him with more targeted data. He tended to rely on feelings more than numbers. It was a root of his populist allure—and also perhaps the reason he didn’t win.

In his concession speech, he positioned himself at the center of a stage decked out with floodlights and speakers and drums, a scene evocative of a rock concert more than a convening of the dejected supporters of a failed candidate and campaign.

“I’m so fucking proud of you guys!” he hollered, eliciting squeals from his fans.

They chanted his name.

“Beto! Beto! Beto!”

After O’Rourke’s recent event in Sioux City, Iowa, I talked to two people who had traveled from different states to see him specifically because of that night. Because they had been inspired by how he spoke about losing. Chris Untiet, 35, had come from California. He works for Habitat for Humanity, and he told me he had watched the speech on the screen of his phone while on a trip to build houses in Vietnam. “I was really moved to tears,” he told me. The other was Claire Campbell. She’s 17. She saw the speech sitting in Sioux Falls, South Dakota, and will vote for the first time in next year’s presidential election. And she hopes she can pick O’Rourke. “I literally love him,” she told me. In the question-and-answer session, she raised her hand and asked him to her prom.

“So, he had to lose the Senate,” Kim Olson, a Democrat and staunch O’Rourke ally who last year lost her bid to be Texas Commissioner of Agriculture, was telling me as I hurtled ahead on a ribbon of road slicing through flat fields, from one Iowa campaign stop to the next. “He had to get the nationwide name recognition. He had to do the hard work. And let me tell you: It’s fricking hard work running as a statewide candidate—as it’s going to be countrywide … grind, every day, all day—and here he is, after losing in a hard-fought race, he said, ‘I’m still going to serve, I’m still going to go, and I’m going to run for president.’ So, yeah, you could say his greatest accomplishment was to lose by, you know, 300,000 votes to a guy who almost won a primary for the president. But that wasn’t his greatest accomplishment. It wasn’t the loss—it’s how he did it—that was his greatest accomplishment. It was going to everywhere, all the time, speaking to people, getting out there, not being afraid of anybody or anything and doing that hard grind that it takes. That’s why it makes him an incredible candidate for president, I think.”

Olson, affable and voluble, in essence attempted to redefine the idea of failure. O’Rourke hadn’t failed. Because he had tried and worked so hard. Because the experience had opened other doors.

At many of the dozen or so O’Rourke events I attended of late, most of the people I talked to knew not a whole lot about him—hardly anything, really, about what he had done, or not done, before the race against Cruz. Maybe they had seen what he said about the kneeling National Football League players in a clip that lit up the internet. Maybe they had seen the Oprah interview. Maybe they had seen the Annie Leibovitz shot on the cover of Vanity Fair. The conversations were a reminder that most people not in Washington or even Texas have basically just met him.

“Is he a lawyer?” 70-year-old Ruth Lux from little Lidderdale, Iowa, asked me after O’Rourke’s pit stop in nearby Carroll.

“No,” I said.

“What did he do before he got into politics?” she asked.

I provided a speedy rundown to the Cruz race.

“I think the fact that he came so close to unseating Cruz, that’s pretty important,” Lux said. “A lot of people are relating to what he’s saying, you know.”

I asked her if she was bothered by O’Rourke’s lack of experience compared with other candidates in the Democratic field. She wasn’t. “I don’t know that Obama had much more,” she said. “Did he really have much more experience than this guy? Really probably not.”

The man who introduced O’Rourke at Iowa Central Community College in Fort Dodge responded similarly. “I heard the same thing in 2008 when I was supporting Obama,” David Drissel, a professor of social sciences, told me. O’Rourke, he pointed out, has not only more congressional experience than Obama but “more congressional experience than the past four presidents combined.” I did the quick math. Trump. Obama. The second Bush. Clinton. True enough.

Obviously, the bar for the requisite experience for the Oval Office has been recalibrated over the past decade or more of presidential campaigns, and doesn’t necessarily run through Congress at all. But voters haven’t entirely abandoned their desire for a candidate to win—and then actually do something. For all the shrugging over his résumé, people at O’Rourke’s town halls clearly, too, were pressing for specifics. I listened to multiple people ask him explicitly to put meat on the bones of his ideas.

Their questions to him often boiled down to one word: How?

Then, when I asked them if they had heard from him what they had wanted to hear, their answers often boiled down to one word as well: No.

Jason Levick, 27, who had driven from Omaha to see O’Rourke, wanted to know how he would cut down on wealth and income inequality.

“A little bit rambling and not really to the point or concrete,” Levick told me.

Brendan Grady, 26, asked O’Rourke in Denison how he would address the “lack of social cohesion.”

“Didn’t really address it,” Grady told me.

Mike Poe, 64, asked O’Rourke in Marshalltown how he would manage to enact meaningful gun control.

“Vague,” Poe told me.

I heard the same thing in South Carolina. In Denmark, at O’Rourke’s town hall in a threadbare auditorium on the campus of tiny Voorhees College, Sailesh S. Radha from Columbia stood up and expressed his frustration that so many presidents can’t seem to make good on their promises after they get elected. How would O’Rourke, Radha wondered, turn his words into actions? Into accomplishments?

After the event, when I asked him what he thought of the answer, Radha shook his head and made a face. “I need to hear more from him,” he said.

And yet, and in spite of a stage of the campaign that’s started to feel more like an ebb than a flow, if I had to divide every crowd into two groups—the squinty, not-quite-satisfied versus those inspired by O’Rourke’s table-hopping battle cries and open to the viability of his candidacy—there was no shortage of dewy-eyed believers.

Many people were struck by his energy and his charisma and his gauzy optimism. They heard echoes of iconic Democrats from the past and saw, they said, a possible path forward—a potential winner—somebody who might be the one to take on Trump. “I’m thinking back to the first encounter with President Obama here at Morningside College,” retiree Mike Goodwin told me after the event in Sioux City.

Lux, meanwhile, the woman in Carroll who thought maybe O’Rourke was a lawyer, waited in line after the event and shook his hand and told Robert Francis O’Rourke he reminded her of … Robert Francis Kennedy. O’Rourke told her thank you. He told her RFK is one of his heroes.

“The charisma,” Lux said when I asked her about the comparison. “The compassion for people at the bottom. Actually, even the physical appearance—the hair, the rolled-up shirt sleeves.”

She told me she had entered 2007 enthused to vote for Hillary Clinton in the caucuses and then for president. But she ended up going for Obama.

“You know, always, it comes down to: How do you present yourself? How charismatic are you?” Lux said. And she said something I heard from many others as well. She was less interested in policy proposals than she was in the possibility of victory. Especially now. “I am more interested,” she said, “in who can unseat Trump.”

It’s one of the few things, it seems, all Democratic voters seem to agree on. “I think that what caucus-goers are looking for is to defeat Donald Trump,” said Norm Sturzenbach, O’Rourke’s state director in Iowa. “That’s ultimately what’s driving it.”

Steinhauser, the GOP strategist from Texas, agreed. “I wouldn’t want to run a campaign against O’Rourke,” he said. He pointed to what he was able to do in … almost beating Cruz. “Look back at what just happened here. It’s pretty incredible. Who else out there on the list really excited people in that way and is the young-looking guy? He reminds a lot of people of Obama or John F. Kennedy or those kinds of candidates.”

Even with his thin résumé? His hazy policies? Steinhauser cut me off.

“Nobody cares,” he said.

“Donald Trump’s policy positions did not matter,” he added, although it should be noted that his visceral pitches in areas like immigration mattered a lot. “I think Democrats want to beat Donald Trump. I think that they’re smart enough to know they need somebody who can win, whatever that means.”

Whether the failed-upward O’Rourke can be that “somebody,” of course, very much remains to be seen. The Iowa caucuses are nearly nine months away, and there’s a long year and a half to go between now and November 2020.

But one recent morning at a seafood restaurant in Ladson, South Carolina, all the booths jammed full, people standing in the back and all the way toward the door, an O’Rourke aide handed the microphone to 69-year-old Stephen Johnson from Mount Pleasant for the last question of the event.

“Congressman O’Rourke,” Johnson said. “I really like you a lot. But there’s one thing I want to know. If you get the Democratic nomination, will you beat Trump?”

O’Rourke answered the question almost before Ladson could finish getting it out of his mouth.

“Yes,” he said.

The people roared.

But putting the word “Blue” on a ball is questionable branding

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