MADISON COUNTY, Va. — Beto O’Rourke, 15 and stewing, wanted to make a break.

To leave his hometown of El Paso. To have a bit of adventure. To get out of his home. To gain some independence from his father, Pat, a county judge and “larger than life figure” whom he loved but with whom he found himself increasingly at odds.

Finding his escape in 1988 through Woodberry Forest School — an elite, all-male boarding school nestled in the Blue Ridge Mountains foothills — he also made a critical choice.

O’Rourke decided then and there that he “wanted to fit in,” that he didn’t “want to have a weird name that people don’t know how to pronounce.” He decided, for the first time, that he would no longer go by his childhood nickname but instead introduce himself by his given name, Robert.

"I'm now a grown-up," he recalled thinking, revisiting his three years at Woodberry in an interview with The Dallas Morning News. "And I want a grown-up name."

Beto, of course, is now a one-word political phenomenon that’s making a return to the national spotlight.

The El Paso Democrat is considering a White House run — to both the bemusement and chagrin of O’Rourke’s detractors, some of whom mock him by calling him Robert — after earning viral attention last year for his closer-than-expected race against Texas Sen. Ted Cruz.

1 / 2When Beto O'Rourke left El Paso to attend an elite boarding school in Virginia, he tried to fit in by ditching his childhood nickname in favor of his given name, "Robert." He quickly found that he still "stuck out so badly" in the new environment.(Ryan Michalesko / Staff Photographer) 2 / 2A Woodberry Forest School yearbook from 1991, when Beto O'Rourke graduated from the elite boarding academy.(Ryan Michalesko / Staff Photographer)

All corners of O'Rourke's life and views will draw closer scrutiny if he ends up vying for the Democratic nomination against President Donald Trump. The ex-congressman refueled expectations Monday both by his words and his involvement in a counter-rally against Trump in El Paso.

His political bearings can be traced back even to Woodberry, though the school may not have shaped him as it did other future politicians who attended over its 130-year history.

O’Rourke had been on campus less than a week when the thrill of it all vanished. He “just stuck out so badly,” new name and all, coming from El Paso’s diverse setting to “almost a monoculture” — white, wealthy and southern — in what seemed like the middle of nowhere, he said.

Amid that teenage trauma, though, he bonded with a handful of other outsiders who cultivated a nonconformist bent that ran counter to the school’s conservative sensibilities.

Punk rock and skateboarding, sure. But also a progressive zeal on issues like gay rights or race relations or the environment that was expressed in spirited conversations over meals; in poems, song lyrics and other writings; and in occasional confrontations with other classmates.

Did O’Rourke know then that he would someday become a politician?

No way, he said without hesitation, sharing a view held by several others who knew him at that time. But a couple of his closest pals, seeing a direct line between the experiences, said they would’ve been surprised if O’Rourke didn’t end up somewhere in the public arena.

“He had so much activism in him,” said Anthony Kim, a California doctor who was one of O’Rourke’s best school friends, recalling the Texan as someone who wanted to "rise up against the power."

“He saw the world as a really unfortunate, unequal place," Kim said.

Woodberry and O'Rourke

Woodberry is often a blip in O’Rourke’s biography.

His time there came after his upbringing in El Paso, where he said he always remained Beto and ended up settling as an adult. It came before his tenure in New York, where he attended Columbia University, attempted a career in music and struggled through what he's called a "little bit of a sad case."

Woodberry is likewise easy to miss driving along the James Madison Highway.

While a historical marker for the school sits across from its well-manicured entrance, the campus is a blur between Civil War battlefields; a burgeoning array of wineries; Madison’s home, Montpelier; and the misty peaks of nearby Shenandoah National Park.

But Woodberry, where tuition these days runs $57,000 a year, is designed to leave a mark on young men.

1 / 3A historical marker stands at the entrance to Woodberry Forest School, an all-boys private boarding school founded in rural Virginia in 1889. Beto O'Rourke attended Woodberry from 1988 to 1991.(Ryan Michalesko / Staff Photographer) 2 / 3Mountains in Shenandoah National Park are seen in the distance overlooking the property at Woodberry Forest School.(Ryan Michalesko / Staff Photographer) 3 / 3A clock is seen in a common area as the sun descends at Woodberry Forest School.(Ryan Michalesko / Staff Photographer)

Classes are six days a week, part of a rigorous academic regimen. Chapel service is a weekly staple, held on Sunday nights during O’Rourke’s time. The group of about 400 students is largely confined to campus, a breathtaking 1,200 acres along the Rapidan River.

One need look no further than the school’s honor system to get a sense of expectations: No lying, no cheating and no stealing.

“There were some foundations that were laid out in front of us,” said John Matthews, who was senior prefect in O'Rourke's class and now works in the construction industry in North Carolina. “We were all told many of the same things: The hard right over the easy wrong. Fear none, respect all.”

O’Rourke learned of the school from his step-grandfather, Fred Korth, who was Navy secretary under John F. Kennedy and who knew that he was looking to get out of El Paso.

That desire to flee sometimes gets short-handed to O’Rourke’s lack of interest in his father’s intense passion for politics. It’s true the younger O’Rourke, at that time, lacked the same conviction. But he said the rift was more broadly about needing space to become his own man.

When O’Rourke learned he would get a generous financial aid package at Woodberry, he said it was a “no-brainer” to leave for a place that was “completely different from El Paso.”

“It was green,” he said, referring to the lush countryside. “The mountains were different than our mountains. It was the East Coast. It was very, very far away.”

Familiar high school experience

Some of O’Rourke’s tenure at Woodberry hits familiar high school notes.

O’Rourke had an Apple IIe computer, and he and his buddies would pile into his room to play games like the Ultima series or SimCity. He participated in track, putting his gangly frame to use as a high jumper. He went on school trips off campus, such as skiing at the nearby Wintergreen Resort.

He and his friends, in their free time, skated around campus or explored new music.

O’Rourke still speaks with reverence about obscure punk albums arriving by mail from D.C.-based Dischord Records or the time a staff member passed him a “Bad Brains” cassette. Among the posters hanging in his C Dorm room was one for the band “The Jesus and Mary Chain.”

He also excelled academically, participating in debate, as well as the Algonquin Society, in which students discussed articles from the likes of The New Yorker and The Atlantic.

Ted Blain, O’Rourke’s English teacher, recently looked at his records and was shocked to learn that he’d given his former student only B-pluses. That wasn’t a bad grade. But Blain couldn’t reconcile those marks with the awards O’Rourke received for writing and American history.

“I guess I was too tough of a grader,” he said with a laugh, recalling O’Rourke as “this very nice, affable, pleasant person.”

But O'Rourke, even after switching to "Robert" or "Rob," also found Woodberry more jarring than he had expected.

The school often had students from Texas. But El Paso not so much. O’Rourke was raised in relative privilege. But at Woodberry, he had to work in the library and as head waiter in the dining hall, while also typing up classmates’ papers for extra cash.

O’Rourke is white. But he lacked the southern identity shared by so many other boys.

“Someone without a southern accent,” Emrah Gultekin, another of O’Rourke’s best friends, recalled thinking the first time he met the Texan.

The South is hard to separate from Woodberry's history.

1 / 4Students, who serve as waiters for meals, set the dining hall tables at Woodberry Forest School.(Ryan Michalesko / Staff Photographer) 2 / 4As the sun descends, a student make his way to the dining hall for dinner at Woodberry Forest School.(Ryan Michalesko / Staff Photographer) 3 / 4Morning light fills St. Andrew's Chapel at Woodberry Forest School, an all-boys boarding school that Beto O'Rourke attended. Chapel service is a weekly fixture at the school.. (Ryan Michalesko / Staff Photographer) 4 / 4Students walk past Kenan Hall as sun descends at Woodberry Forest School in Orange, Va. (Ryan Michalesko / Staff Photographer)

The school was founded after the Civil War by a Confederate captain who served in a famed cavalry battalion known as Mosby’s Rangers. It eventually became a crucible of Jim Crow, an all-white institution that reinforced a Lost Cause sentimentality about the Confederacy.

Woodberry is no longer that kind of school.

It integrated in the late 1960s. Boys are barred from displaying the Confederate flag on campus, as they had been able to even in O’Rourke’s time. Twenty percent of the students are now of color, while another 10 percent come from overseas.

"The current place is so much different and better than it was in my day," said Charles Dew, a noted Williams College historian who reflected with regret on his time as a student at the school in the 1950s as part of his recent memoir, The Making of a Racist.

Woodberry, like many other schools, still wasn’t immune to tensions over race, class and creed.

Some students of O’Rourke’s era remember it as a fairly egalitarian campus where boys were free to be themselves. Others recall a more “oppressive” environment where tradition dictated that older boys would pick on younger students by, say, covering them up with snow.

Walker Carter, an O’Rourke classmate, said it could certainly be intimidating for a “new boy,” particularly if you weren’t part of the in-crowd. He said his own response, coming from Mississippi, was to try to fit in by buying the same sort of clothes the cool kids wore.

“Beto, he just didn’t give a [expletive],” said Carter, who now works at a law firm in D.C.

Or least O’Rourke and his closest friends channeled their anxiety in a different way.

“We were angry people ... sort of trying to find ourselves,” said Gultekin, a California-based entrepreneur who is among those who thought O'Rourke would end up in politics.

O’Rourke closed ranks with the “international students, the nerds, the people who didn’t fit into a group,” he said. The circle of friends developed a reputation as the “Bickering Club,” thanks to their free-wheeling debates over meals that highlighted a political distance from their peers.

They were unabashed in their liberalism — founding, for instance, an environmental group called the Terra Interest Society.

“It is the hope of this organization and its members that the growing problems of our world be brought to attention, and thus by enlightenment, we can undertake the solution of the problems we have created,” the group’s hand-written charter said.

Beto O'Rourke, known at the time as Robert, helped form an environmental club called the Terra Interest Society while he was a student at Woodberry Forest School in Virginia from 1988 to 1991. (Courtesy of Emrah Gultekin)

O'Rourke sometimes clashed with classmates, over issues big and small.

"I had all these sports posters up," said Dave Parrish, who butted heads with O'Rourke, his first roommate, to the point that one of them had to move out. "He had all these punk rock fliers."

O’Rourke also has distinct memories of ripping down a Confederate flag displayed in a common room, of getting mocked for standing up for a kid who was being teased as gay, and of otherwise having a "hard time with some of the cultural dynamics."

Kim, one of his closest pals, remembered a time when O'Rourke even called him out for being mean to a new Hungarian student in their friend group.

"He was always for the little guy," Kim said. "I know it's cliche, talking about him now. ... But those moments really stand out."

The Texan, while resolute in his beliefs, is now almost sheepish about his schoolboy “righteousness.”

He reflects on his time at Woodberry with gratitude, even though he couldn’t wait to leave and hasn’t been back since graduation in 1991. He got an “extraordinary education,” he said, thanks to friends and teachers who gave him a “much greater perspective on the world.”

But he’s also come to realize that he, too, was an immature kid with a lot more still to learn.

“It wasn’t that Woodberry rejected me,” said O'Rourke, who ended up becoming friends with Parrish, that first roommate with whom he clashed. “I probably didn’t give people the benefit of the doubt, or the chance, or assumed too much based on whatever factors beyond these kids’ controls.”