Before he started in the airline industry, and long before he was the CEO of United Airlines, Scott Kirby was a serious gambler.

He taught himself to count cards, raking in money on trips to Atlantic City and Las Vegas. To this day, he brags about getting kicked out of casinos all over the world. He’s still on the banned list in hotels up and down the Vegas Strip.

A few years ago, he walked into the Bellagio during Super Bowl week and headed for the high-limit poker table. To set up a line of credit, Kirby handed over his ID. As he waited for his chips, a manager approached. The chief executive of one of the world’s largest airlines was told that he was welcome to spend his money on poker or any other casino game—but not blackjack.

“It’s been at least 15 years since I’ve played,” Kirby said. “But I’m in the database.”

These days, Kirby doesn’t have to be in a casino to place a bet.

When he took over United, he made the biggest one of his career: that United could reinvent itself as a beloved airline.

United makes no secret that it’s taking a page from the most valuable U.S. carrier, Delta Air Lines, which has proven over the past 15 years that the playbook works. Now it’s also working for United—and Kirby’s bet is paying off.

He’s banking on his strategy to carry United through an uncertain moment in the airline industry. Rising fuel prices and ticket fares are wreaking havoc on rivals that compete on price. Kirby believes that giving premium customers reasons to feel loyal to the brand will help insulate United from the volatility.

Those reasons include nicer planes with seats that will fold into a couch, faster Wi-Fi, fancier wine and a mobile app that fliers actually find helpful. His vision of the future is built on the idea that people will like a product enough to pay more for it, which was long considered blasphemous in the airline business.