Abbot Reflects on Tie to Failed 2020 Contender

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Gabe Fleisher, Executive Editor-in-Chief

To most of the country, he is “Beto,” the would-be Democratic giant-slayer who ignited nationwide enthusiasm in his quest to defeat Ted Cruz but failed to convert that energy into a White House bid.

But to John Burroughs headmaster Andy Abbott, he is still “Robert O’Rourke,” the studious high school senior Abbott remembers from his time teaching at a Virginia prep school.

Woodberry Forest School is a private, all-boys boarding school nestled on the shores of the Rapidan River just outside of Orange, Virginia. The school was founded in 1889 and in the centuries since, numerous prominent young men have matriculated there — members of congress, Cabinet members, diplomats. Its most recent star is alumnus Former Texas Rep. Beto O’Rourke, who ran a nationally-watched Senate campaign in 2018 before launching a 2020 presidential bid that ended in November. The school’s motto is an ancient Latin phrase: A Posse Ad Esse, “From Possibility to Actuality.”

Abbott was hired at the school in 1991, just one month after graduating from college, at the outset of O’Rourke’s senior year. He would remain at Woodberry for ten years, as an English teacher, football coach, and college counselor, until his hiring at Burroughs in 2001. Woodberry is spread over a sprawling 1,200 acres of land, which Abbott remembers as “beautiful” and “truly breathtaking.” The centerpiece of the campus is the headmaster’s house, known as “The Residence.” Legend has it that the edifice was designed by Thomas Jefferson for the family of his presidential successor, James Madison, whose “Montpelier” estate la

Beto O’Rourke’s high school yearbook photo.

ys just ten miles away.

“It’s highly regarded as one of the great Southern boarding schools,” Abbott said of the elite institution, which he compared to Priory or SLU High, due to its Catholic pedagogy.

The now-JBS headmaster didn’t realize that the political star Beto O’Rourke he had been reading about in the news was the Robert O’Rourke he remembered from Woodberry until a former colleague sent him an article in the Dallas Morning News recounting the politician’s early years. “Oh my gosh, that was Robert O’Rourke!” he remembers thinking. “I was pretty impressed … It was cool.”

In Abbott’s recollection, O’Rourke was “considered a very smart guy” in high school. “A really bright guy. He had a reputation for being a good writer and a good student and pretty serious.” Although he never taught or coached the senior, Abbott said that Woodberry was a tightly-knit community, regardless. “It’s a boarding school, so you live at school,” Abbott said. “And there’s only 380 students. And you have dinner together every night. You actually had seated dinner like [Buroughs has] lunch. We had seated dinner, four nights a week. And then you’d all go to chapel together on Sunday nights. And you’d go to Assembly together on Monday mornings. And so it wasn’t just school. You’re living [in] the dorm; you’re living there. So you did pretty much know just about every kid.”

However, their connection was not enough for O’Rourke to win Abbott’s support in the 2020 campaign. “I love all my students and I if I could support one over somebody else for, like, an Oscar or an Emmy, that would be awesome, but ultimately, representing me and my vote, that is not something that I will ever give away because of my devotion to a student,” he declared. “I will have to believe that they truly are the best.”

It did, however, lead to an interview with the New York Times, after a reporter for the newspaper reached out to Abbott to research an article on O’Rourke’s early years.

Abbott didn’t say much to the Times, but he did tell The World that the presidential hopeful’s description of Woodberry in the Dallas Morning News profile caught his eye. In the article, O’Rourke claims that he “stuck out so badly” at Woodberry. He recalls a mostly lonely high school experience, an isolated Texas castaway who had a small circle of few friends.

In Mr. Abbott’s eyes, if O’Rourke felt so lonely, he certainly hid it well. “I did not remember him sticking out … It was a very conservative environment, but if you look at the photograph, he presented as conservative. There were some guys who had really long hair who, in the 1990’s, might have stuck out differently. And he was not one of those guys.”

“I was surprised that he didn’t like Woodberry,” Abbott continued, adding: “There are obviously current seniors at Burroughs who could be miserable who I do not know because they veil their misery so I couldn’t see it, but it was a surprise to me to see that it was a hard time for him.”

A yearbook from the 1991 school year reflects the more-robust high school life Abbott remembers O’Rourke having. He was a member of The Talon, the school’s literary magazine, and the Algnoign Society, which Abbott described as a “literary group” made up of English teacher Ted Blain’s “handpicked” favorites. (Blain, who hired Abbott at Woodberry, was close to O’Rourke during his high school years, according to Abbott.) At the end of his senior year, O’Rourke received two honors from the school: the Robert F. Williams Memorial Medal, for “most imaginative prose or poetry,” and induction into the Cum Laude Society.

Although Abbott acknowledged O’Rourke could have “just assimilated to fit in” and truly felt differently at the time than he presented, the JBS educator also pointed to other parts of that yearbook O’Rourke may have cringed at while gearing up for a presidential run. There are at least two photos in the yearbook containing Confederate flags; another photo is captioned as showing the members of one dorm, “the Upper Taylor Lynch Mob.” The caption describes the dorm as “a typical hang out place,” likely an implicit reference to the lynchings of African-Americans once rampant throughout the South.

I would think anybody in the current political environment, seeing what the history would be, would be wise to get ahead of that narrative

— Mr. Abbott

“I would think anybody in the current political environment, seeing what the history would be, would be wise to get ahead of that narrative,” Mr. Abbott said, citing the recent blackface scandal concerning Virginia Gov. Ralph Northam as an example of how politicians continue to be haunted by images of their early years. (Unlike Northam, there is no evidence that O’Rourke appears in any controversial photos in the yearbook.)

Asked to clarify if he believed O’Rourke’s distancing himself from Woodberry in the Dallas Morning News interview (which was published one month before his presidential announcement) was an act of political expediency on the part of the former Texas congressman, Abbott paused for a full sixteen seconds. “I don’t necessarily think that that’s a negative,” he finally decided. “If it were the case, I think it would be an appropriate thing if you were running for president, and you have concerns about elements from your past or decisions that you made, I think it is prudent to address those at the beginning and not let them come out.”

But the 1991 yearbook also offers evidence that could bolster the future congressman’s description of his time in high school. A song lyric quoted in O’Rourke’s senior paragraph does betray a different side of the young man, a hint at the punk-rock band and profanity-laden presidential campaign he would later lead, as well as the inner anguish he claims to have felt even at Woodberry, to Abbott’s surprise.

“Now I’m the angry son,” the lyric goes. “Everything I’ve learned was wrong. I’m the burning door. Once I’m opened I can’t be closed. I found a hidden wheel. And it rolls to reveal that I’m the angry son.”

“I’m the angry son.”