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I Fought The Law (And The Law Won)


By Bryce Taylor Rudow

Warning: Contains minor spoilers to Breaking Bad and Catch Me If You Can (but honestly, it's been 11 years, and there's a statute of limitation for spoilers).

Last week, Breaking Bad aired its series finale, and despite what one thought of it*, what it was, ultimately, was a reminder of the inevitable ending for men on the run.

They get caught.

But when I heard about 29-year-old Ross Ulbricht, the mastermind behind Silk Road, being arrested, I thought of a different cinematic treasure: the 2002 flick Catch Me If You Can, featuring a pretty impressive Leonardo di Caprio and Tom Hanks combination. The film is a dramatic retelling of the real story of Frank Abagnale, a brilliant teenager who conned his way into millions of dollars and posed successfully as a Pan American World Airways pilot, a doctor from Georgia, and a Louisiana parish prosecutor. For years, the FBI's agent Joe Shea tried to chase him down, only to constantly come up empty-handed.

And until very recently, that was the case with Silk Road, a marketplace located in the Deep Web's Dark Web (if that's confusing, just imagine the Deep Web as Diagon Alley and the Dark Web as Knockturn Alley). There, users could anonymously buy anything from drugs to guns to most other illegal things you can think of, all through the equally anonymous BitCoin system. And while this was still very much a secret realm of the internet, there were whispers of boastings from satisfied users that exclaimed, "The system that's in place makes it impossible to track!"

But that system, as near-flawless as it was, didn't account for human error.


Frank Abagnale, still very much a teenager despite his mature brilliance, actually reached out to his pursuer, Shea, on more than one occasion. He couldn't live the life of a vanished ghost; instead, he wanted to always be the elusive Road Runner. He wanted to prove that no matter who chased him, he would be a few steps ahead. In the end though, it was that hubristic belief that he could never be caught that ultimately led to his capture. He got cocky, he got predictable, and he got comfortable. And when you get comfortable, you stop running for your life; and then you're a dead man.

But Ulbricht, known only at the time as Dread Pirate Roberts, didn't learn that lesson and instead gave an extended interview to Forbes this summer, both as a marketing ploy and a nod to his own genius. In it, he even claimed that he should be on the Forbes' Richest Men in the World list. On top of that, the poorly-hidden guerrilla marketing tactics he used in the beginning of Silk Road's existence, like posting in random forums about the wonders of Silk Road, made him much easier to find.

 To go back to Breaking Bad for a minute, it's worth nothing that the criminal with the best understanding of how to not be caught was the one who distanced himself the most from his illicit affairs: Gus Fring. If it wasn't for that meddling Heisenberg and his desire for revenge beating out his smarter instincts, he would still have both sides of his face and be running his meth/chicken empire. He understood that if you want to succeed, you have to forsake fame, something that neither Abagnale or Ulbricht couldn't do.

So despite a Sawyerian (Twain / Lost pun?) talent as a confidence man, and despite a nearly impenetrable encryption shield, both Frank Abagnale and Ross Ulbricht, respectively, found themselves in handcuffs eventually.


For Ubricht, it was while he was in the science fiction section of the Glen Park branch of the San Francisco Public Library. A handful of plain-clothed FBI agents came into the library, sat around him, and waited for him to open his laptop. But because its hard-drive was encrypted, they had to wait until it was on to confiscate it in order to be able to access its information later. They were patient though, and once Ulbricht finally sat down and logged on, his fate was sealed.

The FBI knew that, like always, a man can't run forever.

* It was fantastic and was the ode to science that it always said it was.