Austinite Ross Ulbricht had what appears to have been a very bad day in the dock in federal court last Thursday, with college buddy Richard Bates testifying that Ulbricht once confessed to him that he was the multi-millionaire mastermind of Silk Road, the Bitcoin-fueled “dark web” site, a.k.a. “the eBay of drugs.”

Bates would have been one of Ulbricht’s only friends not to have been absolutely gobsmacked by his arrest in October 2013. Most of the rest of them thought it, to borrow a catchphrase from one of Ulbricht’s favorite movies, “inconceivable.” (Inspired by The Princess Bride, Ulbricht went by “Dread Pirate Roberts” online.)

Yes, several of them acknowledged, Ulbricht loved to do drugs. Yes, one of them joked, he was a “dirty hippie” and the kind of guy who occasionally stripped at parties and wore a dress to school if he lost a bet.

Few of his old friends would have been surprised to learn that Ulbricht was a dedicated user of Silk Road, but its kingpin? Never.

That assessment goes double for Blake Benthall (seen above on a Galveston beach), who is currently awaiting trial and facing a possible life sentence as the alleged administrator of Silk Road 2.0.

Like Westlake High School grad Ulbricht, Benthall is a Texana native of the the stolidly middle-class Meyerland area of southwest Houston. The two men were both highly intelligent. They were both Eagle Scouts, drawn to computers, and as young adults, they both became ardent acolytes of Ron Paul’s libertarianism and settled in San Francisco.  

That’s where the similarities end, where Benthall emerges as an even unlikelier alleged drug lord candidate than Ulbricht. Benthall was home-schooled and was still, at the time of his arrest, a dedicated churchgoer, just as his parents had raised their only child to be. He’d been programming since he was about nine years old, and was a gifted pianist, a youth division competitor in Houston’s Chopin Society, and later a song parodist who once rewrote a Muse tune country-style.

Unlike Ulbricht, Benthall was no hedonist. As far as anyone knew, he’d never so much as a toked on a single joint in the first 26 years of his life, much less dabbled in anything stronger. He’d dropped out of a Florida Christian college because he didn’t need a degree to start marking big money as a programmer, and as of earlier this year, was working for Elon Musk’s SpaceX.

“By all accounts, just living the dream,” says “Megan,” who has known him since she was about 11 and Benthall about 9. (Fearing the online wrath of Silk Road fans, she’s asked to use a pseudonym.)The two were home-schooled alongside each other in southwest Houston. Megan says that until about a year before his arrest, she remained one of the few friends he would visit on trips back to Houston, when they would usually wind up after a night on the town at venerable late-night taqueria Chapultepec.

Regarding Benthall, she takes what Ulbricht’s friends have said about him—that they could see him using the site, if not running it—a huge step further: “I feel like if someone had told me that he been working with the FBI to take down Silk Road, I would have been like ‘Oh yeah, that makes total sense. The kid is so smart. I am so glad he’s using his talents to take down these sites.’ But the other way around is unfathomable,” she says.  

And yet there it was, on the web, under an FBI letterhead:

Preet Bharara, the United States Attorney for the Southern District of New York, George Venizelos, the Assistant Director-in-Charge of the New York Office of the Federal Bureau of Investigation (“FBI”), and Peter Edge, Executive Associate Director of Homeland Security Investigations (“HSI”), announced today the arrest of BLAKE BENTHALL, a/k/a “Defcon,” in connection with his operation and ownership of the Silk Road 2.0 website…

Manhattan U.S. Attorney Preet Bharara said: “As alleged, Blake Benthall attempted to resurrect Silk Road, a secret website that law enforcement seized last year, by running Silk Road 2.0, a nearly identical criminal enterprise. Let’s be clear—this Silk Road, in whatever form, is the road to prison. Those looking to follow in the footsteps of alleged cybercriminals should understand that we will return as many times as necessary to shut down noxious online criminal bazaars. We don’t get tired.”

“I can’t emphasize enough how unexpected this was—I found out while I was on vacation and replaying every interaction we’d ever had was basically my entire week,” Megan recalls. 

Thoughts of Benthall and a courtroom dredged up a memory of perhaps the most serious mischief she and Benthall had ever engaged in together: an unsanctioned teenaged hooky episode, when she and Benthall slipped away from their home-school co-op to a nearby Starbucks and got caught by the parent-administrator in charge. “She was like ‘Yeah, you really can’t do that, I worry about you guys’ safety, it’s really not cool,’ and Blake was like ‘Okay, we’ll see you in court.’ That was just his sense of humor.”

Megan also recalls the eminently silly commercials Benthall co-produced for their home-school yearbook:

And now here was this gifted goofball facing the full wrath of the United States Department of Justice.

Benthall still has a small army of supporters. His Facebook page overflows with testimonials and messages from friends offering up prayers and telling him to hang in there. Some believe he was set up, somehow, entrapped by the government.

“I am not one of those people,” Megan says. “I am still pretty angry about it. I don’t have any words of support to give. It just kind of baffles me.”

Megan believes that at some point, Benthall allowed his politics to overpower his faith.

“The thing that makes it make sense is for me is that you read about how Ross Ulbricht has very strong libertarian views,” she says. “Blake was always way into Ron Paul, so I think he might have been doing this as a sort of libertarian utopia, where he was like ‘I am the adminstrator of this thing. I am not involved in any of the transactions. That’s all between consenting adults.’ I don’t agree with that at all, but I could see how he would think that.”

There is one last similarity between Ulbricht and Benthall: a jaw-dropping propensity for what seems to be rookie mistakes.

Ross Ulbricht, the alleged founder of the Silk Road, was arrested in October 2013 and linked to the illicit marketplace.

The FBI had a relatively easy time of it, since Ulbricht apparently posted his personal email address, [email protected], on a bitcoin forum where he said he was looking to hire IT pros.

The blunt connection between Ulbricht’s personal and business activities came despite the fact that Ulbricht normally took extensive precautions to mask his online identity, Cook noted.

The alleged founder of the Silk Road 2.0, Blake Benthall, was arrested on Wednesday and it seems he didn’t learn from Ulbricht’s mistake.

The email address [email protected] was connected to the Silk Road 2.0, so when the FBI took down the second iteration of the marketplace, the notification emails went straight to Benthall, the agency said.

Of course, in the case of the Silk Road 2.0, the FBI also had another big advantage: an undercover agent who gained the trust of the website’s moderators before the site even launched.

But to Megan and a few more of Benthall’s oldest friends, that yawning gulf between his unquestioned intelligence and his mind-boggling lack of savvy is among the least of their disillusions.

“The people who we hung out with in high schoolthe people I’m still friends withare in total shock because that’s just not who we are,” she says. “I’ve never even consumed marijuana in any way, and this person who came to my wedding is part of an international drug trafficking conduit? It’s forced me to question everything about whether or not I can really know someone.”

(Photos: Blake Benthall’s Facebook)