The cost was $250,000, which the agreement stated was based on his age. In September 1987, five months after my brother, Josh, was born, and three months after we moved from downtown Chicago into the north suburbs, Dad bought his unlimited lifetime AAirpass. Then, after a good year at Bear, the investment in an unlimited pass made sense.ĭad speaking at an event, organized by American Airlines’ public relations team, where he was asked to donate miles for kids with cancer, circa 2000. When American started the AAdvantage program, Dad and Uncle Shelly (Mom’s uncle and one of Dad’s best friends and business associates) began flying even more than they already did. Airports and airplanes – they were who Dad was. Later, he focused on investment banking, and also became the largest shareholder of the financial corporation Olympic Cascade, the holding company of a brokerage firm, National Securities. Transitioning to finance, Dad moved to Chicago in 1976 for a stint at Smith Barney and, according to him, became the second-highest-grossing stockbroker at Bear Stearns in 1979, where he worked for a decade. “Steven got on a plane like most people get on a bus,” says my mom, Nancy Rothstein, who was married to my father for 36 years. On the weekends, he’d rush to Houston, Dallas, Wichita Falls, Mexico City or Acapulco, then back to work on Monday. He had an apartment in Manhattan on East 89th Street, but mostly, he was at the wallet factory in Oklahoma, or traveling, both for work and play. That December, he joined the wallet business – a company my grandfather had purchased – doing sales. He flew to Europe several times a year and went to live there after graduating in 1972. “I was on my own and could go anywhere at a moment’s notice,” he reminisces. In college he worked for a travel agency helping students book standby flights at low fares, which he utilized himself. He wrote his college application on a typewriter at a hotel beach in Hawaii and mailed it from a post office in Osaka. “I felt as at home in Copenhagen or Paris as I did in New York … I was a child of the world.” “I began to taste, directly, the fervor of foreign travel,” he tells me. Right: Dad, on the phone, and his colleague at the company’s booth at a wallets and clothing trade show in Los Angeles, circa 1973. Left: Dad with his mom in Hawaii on his first around-the-world trip. And I think – as does my whole family, including my dad – that at the very least, it doesn’t quite land. The obvious story is that my father was a decadent jet-setter who either screwed or got screwed by American depends on your take. It’s even a perennially popular conversation topic on Reddit. The legal fight went on for years without going to trial.

My father was one of several lifetime, unlimited AAirpass holders American claimed had breached their contracts.Ī few months later, my father sued American for breaking their deal, and more importantly, taking away something integral to who he was. After 20 years, it seems, they’d decided the pass wasn’t such a good idea. Then, on 13 December 2008, American took the AAirpass away.įor several years, the revenues department at American had been monitoring my father and other AAirpass holders to see how much their golden tickets were costing the airline in lost revenue. All photographs courtesy Caroline Rothstein

One of the many designs that American used for AAirpass.

Airpass benefits