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Tucked inside the first print issue of El Paso’s new alternative weekly newspaper, Stanton Street, in January 2002 was a warning shot from its 29-year-old publisher, Robert F. O’Rourke.

His late father, a county judge and writer who had died in a bicycle accident just a few months earlier, was “the inspiration behind this venture,” O’Rourke wrote. But the letter moved quickly from a memorial to something like a stump speech. His target was the city’s only major English-language newspaper, the Gannett-owned El Paso Times. “Too often we have heard the lament of our fellow El Pasoans who feel neglected and uninspired by the daily paper, beholden to a corporate board that meets in McLean, Virginia, where they don’t know the word adelante and they’ve never heard of Pat O’Rourke.”

The letter ended with a stab at the kind of DIY organizing that would be the hallmark of O’Rourke’s future political campaigns. “As a reader, ask your favorite restaurant, coffee shop and supermarket to carry our paper,” he suggested. “After you finish reading the paper, pass it on to a friend and ask them to do the same.”

Stanton Street took two and a half years to come together and just a few short months to fall apart. But it was a formative experience for O’Rourke. The lifespan of the publication, from its inception as an online-only magazine to its 15-issue run in print, coincided with a period of transformation and turmoil, both in El Paso and in O’Rourke’s own life, and it offered its young publisher a crash course in city politics and community-building. Challenging the city’s establishment in an unfriendly environment, he embraced new platforms and a seat-of-the-pants ethic. Long before he was musing on Medium about Kansas cafes, his fledgling alt-weekly was, in a sense, O’Rourke’s first campaign, and though he did not win, it would lay the foundation for his political career to come.

“It was very pivotal to his development as a political figure,” says Bob Moore, a former El Paso Times editor who has followed O’Rourke’s rise.

O’Rourke, who grew up in El Paso, returned home in 1998 from Brooklyn, where he had lived after graduating from Columbia University in a Williamsburg loft with a hand-operated elevator and a weak furnace. He worked at a moving company and a publishing house, tried his hand at fiction, and played music with friends from his old punk rock band, Foss. It was idyllic but unsatisfying. Looking for something new, he bought a pickup truck, packed up his things, and set off across country.

“In New York, you can struggle for a really, really long time and you can still be a nobody,” says his friend Lisa Degliantoni, who later followed him to Texas to help launch the print version of Stanton Street. “In El Paso, you can be a somebody.”

What O’Rourke decided he wanted to be was an internet entrepreneur. Along with Grace Madden, another friend from New York, he launched a web design company out of his apartment in the summer of 1999 and called it Stanton Street, after the street on which his apartment was located. El Paso’s economy for years had been rooted in low-wage industries like garment manufacturing, but O’Rourke sensed an opportunity for a fresh start for both himself and the city. Charismatic and well-connected, he was a natural salesman, trading in the long hair (and dress) of his Foss days for khakis and blue Oxford button-downs, and conducting seminars around town about why businesses should be on the web.

“Even though he was a businessman, he was still a kind of punk-rock ethos kind of person,” says Chris Cummings, an El Paso real estate developer who has known O’Rourke since they were kids. “[He] didn’t take things super seriously, and seemed to be interested in just having friends.” A few years after his return, O’Rourke joined a short-lived band called The Sheeps, which performed covers of classic punk songs while wearing sheep masks. “Our persona was that we were a very famous band from New Zealand and we didn’t want people to know our true identities,” the band’s bassist, Ailbhe Cormack, told me. (According to O’Rourke, the band members had been listening to a lot of music around this time by New Zealand indie rockers The Clean and the Sydney-based group The Scientists.)

The business soon sprouted a second dimension. Stanton Street would continue to design websites for businesses in El Paso and Chihuahua, but it would also lead by example by starting an online magazine. When StantonStreet.com launched in 1999, it promised to be “the most comprehensive, interactive, and entertaining home page in the Southwest.”

“Both the online newspaper and the web design company kind of started at the same time and ultimately we did one really to be able to do the other,” O’Rourke told me, on a recent break from his cross-country road trip. “I think the real passion was in news and writing and documenting what was going on in El Paso and in Juarez.”

Stanton Street’s digital media offshoot filled a void. Various alternative outlets had popped up over the years in El Paso, but none ever lasted long. “[There] was a newsletter you could subscribe to where you’d get a list of all the shows in town,” recalls Marina Monsisvais, a contributor to the site and, later, the newspaper’s music editor. “But it was like a girl compiling all the shows and sending out an email—it was kind of siloed out that way.”

Here you could check out concert listings, vote in online polls, and enter Oscar pools. There was original writing on bullfighting and City Hall; interviews; weather; and a real-time ticker tracking the peso against the dollar. It was a quintessential product of the internet’s Iron Age, manic and messy but innovative all the same. In an El Paso Times profile of the venture around this time, O’Rourke boasted that the site received 32,000 impressions a month—a pittance by today’s standards but a breakthrough at the time.

A year after it launched, Stanton Street opened a real headquarters for its web design and media projects on the 13th floor of a mostly empty Art Deco tower downtown. A framed album from Austin psychedelic rock group The 13th Floor Elevators greeted visitors. It was a space where young writers and professionals in O’Rourke’s cohort could shoot the breeze. The staff betrayed the essential smallness of a city of 600,000. Mike Stevens, O’Rourke’s ex-bandmate from Foss, had moved west with him from New York and become the managing editor of the website. Sito Negron, a veteran El Paso Times reporter and brother of another of O’Rourke’s former bandmates, covered city politics, first for StantonStreet.com and later as an editor at the print weekly.

The website’s opinion section, “City Talk,” was anchored by O’Rourke’s father, Pat, a larger-than-life figure whose political fortunes had dimmed after a stint as county judge. Pat O’Rourke had helped his son get the publication off the ground and, for a time, been its only writer with any real following. One of the site’s most-read features was a journal Pat wrote while riding his bicycle across the country. “He carried a cell phone with him at a time that not everyone had one and a little laptop computer and would broadcast a dispatch every day, along with some photographs of people he met or things he saw or experiences he had,” O’Rourke recalls. “We published them and it just became this thing where everybody in El Paso was reading his dispatches.” Eighteen years later, as the younger O’Rourke narrates his own cross-country expedition in sparse, Kerouac-ian snippets, his father’s blog reads like a long-lost template:

Someone emailed me and asked what the smells were out on the road. I am not sure what the smells are, but they are not city smells. Not exhaust, not street smells, or industry smells. The smells are of fields and clear air and woods and water and rain and humidity and hay and horses and cows and open country. Good smells, I wish I could be more descriptive. A few days ago, I was riding by myself and smelled the most fragrant of smells and it went on for hours.

As the company’s public face, Beto O’Rourke was most involved on the business side, where he was seeking investors for a move to print. He kept abreast of editorial developments but wrote for the website only sporadically. In 2000, he introduced readers to a new technology called broadband. “[T]hink of bandwidth as a pipe,” he explained. “The bigger the pipe, the more information that can flow through it.” Later that year, foreshadowing an issue he would later turn into a book, he cautioned that the Drug War was overburdening the El Paso court system. Sometimes he reviewed other websites for style and substance. And he periodically chimed in on the site’s message boards, responding to reader questions and posting idiosyncratic queries of his own.

“At the Sierra Grande Lodge restaurant in Truth or Consequences [New Mexico] there is a large stained glass of the Elephant Butte Dam,” he wrote in one 2001 post. “The signature on it indicates that it was done by an El Paso Artist, LW Lili Hoffener, in October 1917. Does anyone know anything about this artist?”

No one did.

Stanton Street was lively and experimental, unafraid to punch up, but there was something deeper underpinning it. Its very existence reflected a dissatisfaction with where the city had ended up. In the late 1990s, El Paso was in a funk, and there was a real argument about how to get out of it. Post-NAFTA, El Paso lost more jobs than any other city in the United States—mostly to Ciudad Juarez, its Mexican neighbor—and city leaders saw their future slipping away. According to the 2000 census, 26,000 people had left the city over the previous decade, and the vast majority were between the ages of 18 and 30.

“At the time, our leading export was intellectual capital—we just had this huge brain drain of young adults going on,” says Moore, the former El Paso Times editor. “And that was one of the things that really affected Beto. In some senses he was part of that, this diaspora that went off into the rest of the world because they didn’t see much opportunity.”

Now that diaspora was coming back. Stanton Street offered a glimpse of an alternative—a crew of smart, creative 20-somethings who had returned home, or never left. They were young people who actually wanted to be in El Paso, writing for an audience of young people who lived in El Paso, and they had their own ideas about how to revitalize their city.

“One of the things that I noticed in a lot of other cities that I lived in or visited or traveled to, from New York to Austin to Dallas to wherever, was that they had an alternative weekly that provided a different take than the daily paper on what was going on at city hall, or on the kinds of shows or the kind of art that a community had to offer,” O’Rourke says. “Maybe stuff that wasn’t safe, wasn’t easy. And I thought that that makes us a place that more people are going to want to come to, or stay in, or find out about in the first place.”

Stanton Street devised walking tours of El Paso’s once-vibrant downtown and published a guide to the neighborhood’s architecture. Writers debated what could be done to make the city more livable for El Pasoans of their generation, and they celebrated the businesses and individuals who were breathing new life into the city.

“It was very much a love letter to El Paso,” Degliantoni says. “That is one of the important things to remember about a city like El Paso that spends so much time getting lambasted by the outside press—you have people who are there because they love it and they want to express that love. I think Beto’s always been deeply in love with the border, and this was his young twenties method of like, ‘Come on everybody, let’s love this town the way I do, check this out, look at what’s happening, let’s celebrate this.’”

The 2001 mayoral race, won by a political insurgent named Ray Caballero (a Democrat, although municipal elections are nonpartisan), marked a turning point for the city and a shining moment for Stanton Street. The website covered the contest obsessively. It didn’t take sides, but the candidate and the website shared a similar diagnosis of the city’s afflictions.

Stanton Street joined forces with a local record store to host a candidate forum on the dance floor of a downtown nightclub—the second question was about “brain drain.” Over the course of the campaign, it grilled the candidates on their plans for downtown, on diversifying the economy, and on making the city more attractive to young people—issues that Caballero, running against the city’s conservative establishment, most effectively championed. On Election Day, youth turnout jumped 50 percent over the previous election.

In the midst of the mayoral election, riding high off not only the enthusiasm of the moment but their own successes, O’Rourke and his staff plotted the company’s next big step.

“I had the great idea,” he says, “just as the rest of the world’s figuring out that the future is digital [and] it’s going to come at the expense of print—as we’d built up this really nice digital platform for news, the only real alternative to the El Paso Times and to the corporate broadcast media, just as we really hit our stride—that I was going to push us to do a print weekly.”

O’Rourke convinced Degliantoni to leave New York, where she’d been an editor at Spy magazine, to come to El Paso to get the print edition off the ground. They hired designers and studied distribution models. “We wanted to be El Paso’s Village Voice,” says Monsisvais, who would go on to work at the city’s first alternative rock station.

Then tragedy intervened. In July 2001, a few weeks after the election, Pat O’Rourke was struck and killed by a car while riding his recumbent bicycle in southern New Mexico, just outside El Paso’s city limits. It was a crushing blow to the younger O’Rourke—and also a serious blow to the paper on the eve of its launch.

“Selfishly, I knew we had lost at least half of any chance we had to succeed,” Negron would later write in an essay for the now-defunct El Paso magazine El Bridge.

In the last week of January 2002, the inaugural print issue of Stanton Street landed with a splash, dropping 20,000 copies in 100 locations across the city. The first cover, a “40 under 40” feature, was as defiant as O’Rourke’s open letter. A cliché in New York or Chicago, perhaps even the stuff of sterile business journals, it amounted to an almost-generational call to arms in a city young people once called “Hell Paso” and a rebuttal to the brain-drain narrative.

Over the next few months, the small staff cranked out some of their best work. One cover story, “Teenage Mule,” featured the confessional of a 16-year-old who hauled drugs over the international bridge from Mexico. Another, “Citizen Colonia,” reported on county communities without paved roads or running water. The paper covered City Hall; interviewed the mayor; profiled local bands; and, as an expression of the staff’s binational outlook, featured regular dispatches from writers living in Juarez.

One thing Stanton Street never had was money. “We had the readership, we had the followership, we had the community support, but we didn’t have it when it came to paying for it,” Monsisvais says. “We were really good at content, we just were not good business salespeople.” O’Rourke was using revenue from the company’s profitable web-development projects while he sought outside funding to keep the paper afloat. But the backing never materialized.

“First of all, it was perhaps one of the worst times to do something like this,” O’Rourke says now. “And it also wasn’t sufficiently capitalized—I mean, we didn’t really have an entire year’s worth of capital to be able to operate on, and it was dragging the design and website and software development business under with it. When there was really no other choice, we pulled the plug.”

The end was in sight by the middle of May 2002, when the cover of Stanton Street featured a mock-up of an El Paso Times vending machine being flushed down a toilet. The full-page polemic it teased attacked the city’s English-language daily as conservative, corporate, and out of the step with the community it purported to cover. It was a bit raw and the sourcing a little thin, but in spirit, it captured the essence of what O’Rourke had argued in his publisher’s note four months earlier: El Paso was a city that deserved better from its institutions. Stanton Street put out one more issue. Then El Paso’s Village Voice went down the tubes for good.

Shortly after the newspaper shut down, the online news site shuttered too. Hoping to fill at least some of the void in the city’s progressive scene, O’Rourke helped a roommate, Anthony Martinez, launch a new site called Newspaper Tree in 2003. Stanton Street’s IT side, which was actually profitable, built and hosted the website, and O’Rourke gave Martinez his old newspaper’s email list.

But O’Rourke quickly found another outlet for the ideas and ambitions that had fueled Stanton Street. Though he’d been exposed to politics from an early age through his father, it was “never something that I had really thought about or considered,” O’Rourke says. “But the more we wrote about city hall and city policy and the people who are making it, the more interesting that became to me.”

In early 2005, after friends talked him out of running for the job his father once held—county judge—O’Rourke decided to run for city council on a slate that included two former Stanton Street contributors, Susie Byrd and Steve Ortega, who, like him, had viewed the Caballero campaign as a watershed. They won.

Caballero had been defeated after just one two-year term, but with his acolytes now in government, the agenda that fueled his first campaign continued to set the terms of the debate. The new council set to work almost immediately on the project that would come to be O’Rourke’s legacy in municipal politics: an ambitious and polarizing plan to remake downtown. It would be eight more years before he took his act—and memories of his days as an alt-weekly publisher—to the national stage.

Additional reporting by Jacqueline Aguirre.