As of last night, 2018 Texas Senate race loser Beto O’Rourke is officially running for the 2020 Democratic presidential nomination.

FILE – IN this June 22, 2018 file photo, Beto O’Rourke speaks during the general session at the Texas Democratic Convention in Fort Worth, Texas. Police documents reveal previously unreported details about a decades-old drunken-driving arrest of the Democratic Senate candidate. O’Rourke has long acknowledged the 1998 drunken-driving arrest, saying he made a serious mistake. (AP Photo/Richard W. Rodriguez, File)

Beto has made a bunch of missteps lately, ranging from live-casting a dentist’s visit (weird) to spending a ton of time without his family on the trail pre-campaign, which led to some progressives calling him out for behavior that they believe would never be tolerated from a female candidate.

But in today’s hyper-woke progressive movement, Beto might have another problem. It’s not just that he’s really, really white (despite his nickname) or that he’s also obviously male (remember Sen. Kirsten Gillibrand’s comment that the future is “female” and “intersectional”). It’s that Beto actually comes from about the most stereotypically “white male privilege” background going.

For those unfamiliar, O’Rourke attended Woodberry Forest School in Virginia. Not only is it a boarding school; it’s a boys-only boarding school. And it is super elite and establishment.

As stupid as analyses of big league political figures’ high school backgrounds may be, since the Left has done this with Brett Kavanaugh, Mitt Romney and others, it’s only fair that Beto be treated to the same. So, let’s have a look at his high school, the place he spent a formative period growing up.

Woodberry Forest touts itself as a “school built for boys.” It’s right there on its homepage.

The school has been around since 1889. It was, in fact, founded by Captain Robert Stringfellow Walker, who was a Confederate cavalry soldier in the Civil War.

Specifically, Walker was a member of Mosby’s Rangers, also known as Mosby’s Raiders and Mosby’s Men, which was a battalion that engaged in “lightning strike” raids on Union forces. Union troops struggled to corner and capture them, and they gained a reputation for successfully disrupting US government supply lines and communications.

According to a newspaper obituary, Walker was “one of the first to join the Confederate forces.” At least as late as 2013, he was still being celebrated in special chapel services at Woodberry.

Notably, Mosby’s men, presumably including Walker, led the so-called “Greenback Raid,” which involved derailing a train and stealing $170,000 in Union soldiers’ pay, which was split roughly $2,000 apiece between Mosby’s men.

This reputation for disruption and straight-up theft caused Mosby’s men not just to be reviled by Union forces, but also by fellow Confederates.

Confederate Brigadier General Thomas Rosser wanted Mosby removed from command and viewed the battalion as early day media-whore thieves.

General Robert E. Lee also wanted the battalion disbanded, though that did not occur until after Lee’s surrender at Appomattox.



Unlike Lee, Walker’s battalion never actually surrendered at the end of the Civil War.



Fast forward close to a century, and one finds that Woodberry was also more resistant to integration in mid-20th century America than its chief rival, Virginia Episcopal School.

While Woodberry officially desegregated in 1969, VES took in African-American students several years earlier.

Woodberry’s desegregation also appears to have been the result of direct student-to-student, and then student-to-administration lobbying in which an African-American VES student talked to an all-white group of Woodberry students, who subsequently demanded Woodberry take in African-American students. The school apparently agreed to admit three African-American students funded by a private foundation, but the idea of de-segregation had apparently not occurred to Woodberry until its students demanded it.



There’s lots of emphasis on Woodberry’s “About” page about its focus on Christian values, which we all may appreciate but likely the progressive base will not.

However, Woodberry’s history as a school founded by a Confederate soldier who was not just a rank-and-file guy enlisted perhaps begrudgingly, but an eager participant and member of a battalion not exactly revered for its “honor” and in fact reviled even by fellow Confederates should raise more questions.

Did O’Rourke ever participate in chapel memorials commemorating the school’s founder? What is his view of him, in light of the ongoing debate in Virginia, specifically, about Confederate memorials and lionizing of prominent Confederates?

Despite having technically integrated in 1969, a review of the school’s website makes it look pretty stereotypically white and upper-crust– and again, it’s an all-boys boarding school. Isn’t that at odds with the values of the modern day Democratic Party as we are supposed to understand them? And what is Beto’s answer to that question?

It’s going to be entertaining to see which Democratic contender pounces first on Beto’s extremely “white male privilege” background, because his attendance at Woodberry appears to be a perfect encapsulation of that knock on him.



