Not long after he was elected to a seat on the El Paso City Council in 2005, Beto O’Rourke dropped by a book party at a downtown hotel and picked up a present for his soon-to-be father-in-law. William D. Sanders was an El Paso legend. One of the city’s richest men, he’d done business in 13 countries and made friends in high places. He owned a ranch the size of Omaha and, through his company, a vast stretch of the southern border in New Mexico, where he planned to build a city from scratch rising up out of the desert.

Sanders, a frequent Republican donor described as reticent to the point of secrecy, and O’Rourke, a punk rocker with a progressive streak, did not immediately hit it off. Their relationship started so poorly just a few months earlier that Sanders’ daughter Amy nearly broke off the engagement. But the book that O’Rourke gave to Sanders, Ringside Seat to a Revolution, by an El Paso historian named David Dorado Romo, concerned a subject of mutual interest—the rich history of the city’s downtown and of the Mexican American neighborhoods that enveloped it. It was a paean to the city’s status as the estuarial zone of the continent, where two worlds overlap. In the days after the wedding, O’Rourke later told a friend, he and Sanders traded notes each morning about what they’d learned from the book.

O’Rourke argued in 2006 that Ringside Seat to a Revolution showed that “the more we attempted to deny that Mexico is the true lifeblood of El Paso, the more we declined.” As he cultivated a national identity as a champion of the borderlands in the years that followed, he returned to that theme again and again, occasionally citing Romo’s book in interviews.

And yet, less than a year after O’Rourke gave the book to his father-in-law, Sanders unveiled a plan that proposed turning large chunks of the neighborhoods it celebrated into parking lots—and O’Rourke, to the dismay of South El Paso activists including Romo, was right there with him. Political opposites in many ways, they linked arms in the ugliest battle of O’Rourke’s political career. Half a decade later, a hefty check from Sanders helped send O’Rourke to Congress. O’Rourke has risen rapidly in Democratic politics by being many things to many people, eschewing labels in the service of a feel-good style that appeals to Berniecrats and business types alike. But such slipperiness can cut both ways. O’Rourke, who now calls his father-in-law a mentor, has been dogged by that relationship in every race he’s run in because the contrasts with his own political identity seem so stark—a Democratic insurgent whose career has been boosted by Republicans, and a champion of the border who backed a plan to uproot one of its oldest neighborhoods. In the hands of his rivals, Sanders is O’Rourke’s political shadow, forever distorting his progressive image into something ominous.

William D. Sanders, 77, was raised in El Paso with the business of the border in his blood. He traces his entrepreneurial gifts to his grandfather Ed Sanders, an industrialist who was driven out of Chihua­hua by Pancho Villa but returned to Mexico to make tractors and cottonseed oil. A street in Juárez still bears his name.

With a plan to make his first million by age 30, William Sanders, after a few early failures, found his calling in real estate. By 27, he had his own company; by 29, he’d renamed it LaSalle Partners and moved it to Chicago, where he would make a fortune managing the holdings of corporate giants like Coca­-Cola. Eventually, he sold his shares and decamped with his wife and five kids to an 84,000-acre ranch in New Mexico. There, in 1991, he launched Security Capital Group, the outfit that in the eyes of peers would mark Sanders as a visionary.

In an industry known for grandstanding, Sanders was sobriety distilled, a reserved figure who’d rather build a Walmart than a Saks Fifth Avenue. (A newspaper once complained that it couldn’t find a color photo of Sanders.)

“I remember him telling me and others that he really didn’t have any hobbies—didn’t drink, didn’t play golf,” says Bob Cook, an El Paso business consultant. “His hobby was making money.”

I am running to serve you as the next president. The challenges we face are the greatest in living memory. No one person can meet them on their own. Only this country can do that, and only if we build a movement that includes all of us. Say you're in: https://t.co/EKLdkVET2u pic.twitter.com/lainXyvG2n — Beto O'Rourke (@BetoORourke) March 14, 2019

Eventually, Sanders decided the next big thing was El Paso. “I wanted to be in an area without a lot of competition, and with a lot of growth,” he told a real estate publication. There amid the mesquite was a developer’s dream: the chance to reshape a city—and perhaps build one of his own. He anticipated a future in which everything would be securitized, and he seized on a then-obscure form of real estate finance called the Real Estate Invest­ment Trust, which bundled various properties into publicly traded entities. Sanders’ REITs focused on mundane but essential cogs in the machinery of commerce: parking garages and self-storage units, extended-stay hotels, office parks, shopping centers. By 1998, Security Capital controlled $10 billion in real estate assets. Bloomberg called Sanders “perhaps the most powerful landlord in the country.”

“I remember him telling me and others that he really didn’t have any hobbies—didn’t drink, didn’t play golf. His hobby was making money.”

Flush with cash after selling Security Capital for around $4 billion in 2002, Sanders got started on two big projects after moving back to El Paso. The first centered around the new international port of entry at Santa Teresa, about 15 miles west of El Paso, where New Mexico and Chihuahua meet. In the 1970s and ’80s, an ex–ranch hand named Charlie Crowder acquired upward of 20,000 acres and generous water rights there with visions of a binational utopia—factories with conveyor belts moving products from one country to the other, alongside new housing to ease the “human misery” of the border industrial economy. But the project had stalled. Through a new company called Verde Group, Sanders acquired the land, then went to court for Crowder’s water rights. Blueprints for a master-planned community of 100,000 people surrounding the port of entry began to take shape, with plans in the works for similar developments spanning the border from San Diego to McAllen.

While Verde gobbled up land, Sanders was devising a new set of plans for El Paso, the city he called “the biggest failure that I know of in the United States.” The rise of cheap Mexican manu­facturing, fueled by NAFTA, had hit the city hard, as companies moved their operations across the river. City leaders obsessed over “brain drain.” Compared with the skyscrapers of Chicago and the aesthetic discipline of Santa Fe, El Paso’s squat, strip-mall features would have seemed striking to Sanders in their blandness. What was needed, he believed, was a new downtown.

Around the time Sanders returned to El Paso after three decades away, a 25-year-old O’Rourke moved home under less triumphant circumstances, following a few postcollege years in New York City. After his punk group disbanded, he’d held down jobs as a nanny and a publishing assistant and struggled to make his mark. Back in West Texas, though, O’Rourke thrived. He launched a successful tech company and a punchy, though short-lived, weekly newspaper. By 2004, he was already flirting with a run for office when Amy Sanders, the fourth of the developer’s five kids, moved in with her parents after a year teaching in Guatemala. With a nudge from family—O’Rourke’s mother and Amy’s aunt are close—the two went on a date in Juárez. Three months later, O’Rourke trekked to Sanders’ El Paso office to ask for his blessing.

“He proceeds for the next 10 minutes to talk about her last boyfriend,” O’Rourke told his friend Joe Kennedy III, the Massachusetts congressman, during a Facebook Live session last year. “He’s like, you know, ‘Tom was a really great guy. They were close. There really seemed like there was a future.’ And I think he’s gonna turn the corner and say, ‘But, really glad’—and then there’s no ‘but.’” A weekend getaway with both families in New Mexico only made things worse. When the son-in-law-to-be returned to El Paso, Amy threatened to call the wedding off.

“Why, because your dad’s such a jerk?” O’Rourke recalled saying. The two men eventually patched things up, and within a year, they were allies. Amy Sanders now jokes that Beto is her dad’s “favorite child.”

In May 2005, four months before the wedding, O’Rourke won a seat on the City Council representing a district that included some of the city’s richest neighborhoods, as well as some of its oldest (and poorest) Mexican American communities. One of the first items on the council’s agenda was an ambitious downtown revitalization plan pushed by Sanders.

Overhauling downtown had become a cliché in El Paso, a lost cause pursued unceasingly for decades. But the Sanders plan, under the auspices of a new civic organization called the Paso del Norte Group, was different. PDNG was helmed by some of the most powerful businessmen in El Paso and Juárez, including oil billionaire Paul Foster, and Woody Hunt, who had made a fortune building military housing. It was modeled on the Commercial Club of Chicago, which had sponsored Daniel Burnham’s famous plan for the city, and which Sanders had been a member of decades earlier. PDNG’s roster of members grew to more than 350 people—including O’Rourke—who paid annual dues of as much as $1,800.

“We can’t save a building just because Pancho Villa had a couple of drinks there.”

The city gave PDNG $250,000 to come up with a plan (a federal grant and membership funds provided the rest), and in March 2006, Sanders presented the result at the Plaza Theatre in downtown El Paso. He proposed using a REIT to fund a range of amenities, including an arena, big-box stores, condos, and a walkable new arts district. To clear the way for such an approach, the city would need to greenlight the redevelopment of not just the immediate downtown, with its derelict art deco gems, but large swaths of El Segundo Barrio and Duranguito, historic Mexican American neighborhoods that hugged the Rio Grande just south of it. He opened by quoting Burnham’s famous line—“make no little plans; they have no magic to stir men’s blood.” The City Council, including O’Rourke, voted to move forward with the plan that day.

Then things started to go wrong. After a career spent comfortably out of the public eye, Sanders had made himself the face of a project, and his inexperience showed. Though he had some of the trappings of a native son—bilingual, deep roots, his own cattle brand—he’d made his money elsewhere. A newspaper profile from his time in Chicago described him as “establishment” and “tweedy.” That’s not El Paso. And Sanders was upfront about what redevelopment would entail. If proponents couldn’t convince property owners to relocate on their own, he told a group of businesspeople, they would “have to flex our muscles and use eminent domain.”

A range of interests quickly mobilized against it, including business owners worried about a forced relocation. But no group was louder or more forceful than the group of barrio residents, defiantly called Paso del Sur, organized by David Romo. In a letter, members warned, “We are not prepared to sit idly by and watch this ethnic cleansing of an historic neighborhood and its people take place.”

In Romo’s El Paso, every block told a story—the brick building where the revolutionary mystic Teresita Urrea lived; the home where Pancho Villa stashed his money. O’Rourke tactfully argued that without some sort of framework, the city would be powerless to prevent such haunts from turning “into bus depots, warehouses, and trinket shops that sell plastic goods.” But Sanders only toughened activists’ resolve. “We can’t save a building just because Pancho Villa had a couple of drinks there,” he told one local architect. (Sanders declined to comment for this story.)

O’Rourke had still been a member of PDNG when he took his first vote on PDNG’s plan, and he became a lightning rod for furious activists, who filed ethics complaints accusing him of various conflicts of interest. Some of the criticisms of O’Rourke were unfair. He had been obsessed with fixing up downtown long before Sanders entered the picture. At one forum, a Paso del Sur leader accused him of using a Spanish nickname to pass himself off as Latino—a criticism that Republicans would eagerly run with during the 2018 campaign—but O’Rourke has had his nickname since childhood.

Eventually he recused himself from many (though not all) votes relating to the plan, and the ethics complaints were thrown out. Properties in El Segundo Barrio were taken off the table. The city never used eminent domain. And proponents of the plan are still indignant at how it’s been framed. “All this nonsense about [how] Beto was gonna use eminent domain to wipe out El Segundo Barrio and gentrify it and all that for his father-in-law is absolutely not true,” says Joyce Wilson, who was city manager during the downtown fight. The public process, in their view, worked as intended.

O’Rourke was a ubiquitous presence in El Segundo Barrio during the battle, riding his bike to meetings and going door to door to make his pitch. Steve Ortega, a close friend who served with O’Rourke on the City Council, points out that he won the barrio in his next campaign and was reelected overwhelmingly to Congress. “I think Beto’s reelection history in El Paso kind of speaks for itself,” he says. “He’s the most popular guy in town, across all demographics.” To people like Romo, the downtown fight wasn’t just about the redevelopment zone. It was about whether a small group of powerful people like Bill Sanders would continue to exert their will on El Paso, a Mexican American city long dominated by a mostly Anglo elite. As Jerry Pacheco, a Santa Teresa developer, puts it, only somewhat facetiously, “You can count on one hand the families that run El Paso, and they’re all Republican.” So it was only natural that the backlash to the downtown plan spilled over into resistance to Sanders’ development near Santa Teresa, too. Activists in South El Paso found parallels in the plight of a squatter community called Lomas de Poleo, just east of Verde’s property, on the Mexican side, where families who had lived there for decades were being uprooted, in some cases violently, by powerful Mexican landowners who stood to get rich off the new nearby developments.

The fight, as intensely personal as it was—O’Rourke accused his critics of putting a “stain on my honor and personal reputation”—did little to slow O’Rourke’s rise in El Paso. By the end of 2011, he was running for Congress. O’Rourke’s campaign was awash in money from leading El Paso Republicans, many of whom had been involved with PDNG and viewed him as the best candidate for the business community. And Sanders helped out in his own way. Through a company he owned, he gave nearly $40,000 to a super-PAC called the Campaign for Primary Accountability, which targeted incumbent lawmakers of both parties. When Sanders made his first donation, at the end of December 2011, the group hadn’t signaled its intent to go after Rep. Silvestre Reyes, the Democratic incumbent. But a month before the primary, it unloaded on the eight-term congressman with ads and mailers accusing Reyes of using political connections to enrich his family.

Reyes responded by going after Sanders. In TV ads, he hammered O’Rourke as the candidate of the 1 percent, and for his support “for destroying homes in Segundo Barrio.” He sent out mailers and gave speeches warning that O’Rourke would help out his father-in-law by building a new international bridge, displacing thousands of people. The literature featured a bulldozer and asked, “Will your neighborhood be next?” (O’Rourke opposed the bridge in the City Council.)

Reyes was an El Paso icon who had re­invented the modern Border Patrol, and he was backed by the last two Democratic presidents. In a precursor to the 2018 Senate race, O’Rourke knocked on over 16,000 doors. But what allowed him to avoid a runoff by just a few hundred votes was an abnormally high number of Republican voters, who chose to participate in a Democratic primary and preferred O’Rourke overwhelmingly. Those voters had been targeted by the Campaign for Primary Accountability.

When I visited El Paso in late February, a few weeks before O’Rourke launched his presidential campaign, Romo agreed to show me around the neighborhood at the center of Sanders’ controversial plan. He fidgeted with a map of the proposed project, swerving slightly as he pointed out landmarks with his free hand. “You see right here?” he asked as we passed the Border Farmworkers Center, a nonprofit that provides social services for Mexican laborers. He pointed back to the map. “P—for parking.”

We parked across the street from Sacred Heart Church, a venerable old brick building that was the epicenter of the resistance to the downtown plan, and Romo drew my attention to a mural he’d helped design in 2006, when the church’s future seemed under threat. It contained a pastiche of characters from the neighborhood’s past, including Villa himself, noshing from a plate of flautas.

Toward the end of his first term in Congress, O’Rourke took a New York Times reporter to the barrio to show off its heritage. “He gave them a walking tour, kind of like what I’m doing, and he said this is the coolest place—like he gives himself street cred,” Romo said. The piece featured a quick guide to the neighborhood’s Mexican American murals, including the one we were sitting in front of. To Romo, it was “the irony of ironies.”

“This was done in order to stop his efforts to destroy this,” he said, gesturing to the neighborhood around him.

Sanders’ grand plans never panned out. The Great Recession, and a state constitutional amendment curtailing eminent domain, thwarted the most ambitious plans for downtown, and after a promising start at Santa Teresa, the economic collapse left little market for a chain of master-planned binational communities. El Segundo Barrio was left untouched, although a proposed arena in Duranguito, in the location identified by the downtown plan, has uprooted dozens of residents. (O’Rourke came out against the arena.) When Sanders’ PDNG lobbied the City Council to build a minor league baseball stadium downtown in 2012, they found a more creative way to evade issues of displacement—they bulldozed City Hall and built the stadium there. (City offices are now split up across several buildings.) O’Rourke declined to comment for this piece, though in a recent interview with the American Prospect, he expressed regret for his handling of the downtown controversy, saying he did a “really poor job of listening.” But the issues raised by the downtown fight are very much a live grenade for O’Rourke. The controversy, and his relationship with Sanders, became a central part of the attacks leveled against him by Republican Sen. Ted Cruz and Republican outside groups during O’Rourke’s 2018 campaign for US Senate. As a rule, the kinds of people who are sympathetic to the plight of Mexican immigrant neighborhoods rarely vote Republican, and complaints about developers carry less weight when they come from supporters of President Donald Trump. Even Romo pushed back against Cruz’s embrace of the barrio. But in a crowded 2020 primary, a heavy-handed embrace of gentrification or a reliance on deep-pocketed donors will be fair game, as will O’Rourke’s sometimes uneasy place as a rich white guy in a historically diverse field.

“This was done in order to stop his efforts to destroy this.”

Already, some progressives have begun to scrutinize O’Rourke’s more business-friendly positions, including his support for free-trade deals such as the Trans-Pacific Partner­ship, and he has come under fire for violating a 2018 campaign pledge not to accept money from fossil fuel executives. (Sanders was, until recently, on the board of an oil company, and one of the largest donors to the Campaign for Primary Accountability was Texas oilman Tim Dunn.) The party is in the midst of a fundamental debate over concentrated wealth; his net worth, and his family’s, will likely become part of that. One Democratic strategist suggested to Vanity Fair that in the months ahead, voters would finally get to know him as “a rich frat boy from West Texas.”

A few weeks after I parted ways with Romo, O’Rourke was off to Iowa for the start of a presidential campaign in which, for the first time in his career, he’d begin as something other than an underdog. But just before he made it official, the conservative super-PAC Club for Growth Action welcomed him to the race with a two-minute video, rehashing his support for the downtown plan and accusing him of doing “his father-in-law’s bidding.” A bulldozer flashed across the screen, and Sanders’ face hovered in the background. O’Rourke was back in the spotlight. And there was that shadow again.