American Kingpin: Catching the Billion-Dollar Baron of the Dark Web

by Nick Bilton

MOST PEOPLE GO through life thinking that tomorrow they’re going to do something great. Tomorrow will be the day that they wake up and discover what they were put on this earth to do. But then tomorrow comes—and goes. As does the next day. Before long, they realize that there aren’t that many tomorrows left.

“The question isn’t who is going to let me; it’s who is going to stop me.”

“Gambler’s Ruin problem,” a theory that no matter how much money you have in a betting scenario, the casino (or house) has an infinite amount of money, and therefore, if you keep making bets, the house will eventually win. Gary reasoned that the same theory was true for DPR and the Silk Road. The U.S. government was the casino; DPR was the gambler. Eventually, Gary believed, because the Dread Pirate Roberts wouldn’t stop playing, he would lose.