Meet the Man Who Flies Around the World for Free
J Thoendell stashed this in Travel
The boarding procedure has barely started at Chicago O'Hare, and Ben Schlappig has already taken over the first-class cabin. Inside Cathay Pacific Flight 807 bound for Hong Kong, he's passing out a couple of hundred dollars' worth of designer chocolates to a small swarm of giggling flight attendants. The six suites in this leather-bound playpen of faux mahogany and fresh-cut flowers comprise the inner sanctum of commercial flight that few ever witness. They're mostly empty now, save for two men in their twenties who seem even giddier than the flight attendants. The two stand to greet him. "This is so cool!" exclaims one, and soon Schlappig is ordering champagne for everyone.
This sort of thing happens to Schlappig nearly everywhere he goes. On this trip, his fans will witness Schlappig's latest mission: a weekend jaunt that will slingshoot him across East Asia — Hong Kong, Jakarta, Tokyo — and back to New York, in 69 hours. He'll rarely leave the airports, and when he does he'll rest his head only in luxury hotels. With wide ears, Buddy Holly glasses and a shock of strawberry-blond hair, Schlappig resembles Ralphie from A Christmas Story if he'd grown up to become a J. Crew model. Back beyond the curtain in business class, a dozen jowly faces cast a stony gaze on the crescendos of laughter and spilled champagne — another spoiled trust-fund kid, they've judged, living off his parents' largesse. But Schlappig has a job. This is his job.Schlappig, 25, is one of the biggest stars among an elite group of obsessive flyers whose mission is to outwit the airlines. They're self-styled competitors with a singular objective: fly for free, as much as they can, without getting caught. In the past 20 years, the Internet has drawn together this strange band of savants with an odd mix of skills: the digital talent of a code writer, a lawyer's love affair with fine print, and a passion for airline bureaucracy. It's a whirring hive mind of IT whizzes, stats majors, aviation nerds and everyone else you knew who skipped the prom.
Imagine if he used that extraordinary brain of his to solve the world's problems.
One of the fundamental steps a Hobbyist can take is choosing an airline to compete for top-tier loyalty status; Schlappig chose United. Nothing was free up front — the object of the game was a return on investment. A Hobbyist doesn't spend unless he can get the same or greater value in return. It took Schlappig about a year to master the dozens of convoluted techniques, exploiting mistakes in ticketing algorithms and learning the ins and outs of the frequent-flyer programs airlines had created after deregulation in the late 1970s. The second leg of the game is credit cards — collecting and canceling as many as possible, and deploying a series of tricks to reap the reward points that bank-and-airline-card partnerships would virtually give away. As he delved deeper, Schlappig learned about a third level, a closely guarded practice called Manufacture Spend, where Hobbyists harness the power of the multitudes of credit cards in their pockets. Airline-affiliated credit cards award points for every dollar spent, so over the decades, Hobbyists manipulated the system by putting purchases on credit cards without ultimately spending anything at all. At its simplest, this included purchasing dollar coins from the U.S. Mint with a credit card and immediately using them to pay off the charge. Schlappig read one detailed post after another that insisted Manufacture Spend was the only true way to fly for free — like sliding a coin into a slot machine and yanking it back with clear string.
Eventually, the best way he learned to visualize this bureaucratic gamesmanship was to see it as a series of table games on a sprawling casino floor — and if the airlines were the house, Schlappig realized, the Hobbyists were the card-counters.