This Airline CEO Was Banned From Casinos for Card Counting — Now He’s Making His Biggest Bet Yet

Scott Kirby went all-in on premium cabins, faster Wi-Fi, and brand loyalty — lifting United into direct competition with Delta.

By Jonathan Small | edited by Dan Bova | Apr 27, 2026
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Before Scott Kirby became CEO of United Airlines, he was banned from blackjack tables across Las Vegas for counting cards. Now he’s applied that same risk-taking to one of the biggest bets in the airline industry.

When Kirby took over United in 2020, he wagered that customers would pay more for a better flying experience. The industry had long believed air travel was a commodity where only price and schedule mattered. Kirby disagreed. He ordered 270 new planes from Boeing and Airbus, reinstalled seatback screens that rivals had ripped out, struck a deal with Starlink for high-speed Wi-Fi and dumped the industry’s most-hated aircraft — the cramped 50-seat regional jet.

He seems to have hit the jackpot. United shares have doubled since early 2021, while most major U.S. airlines, except Delta, have seen their stock prices fall. Last year, Delta and United accounted for over 90% of the industry’s profits. But despite lifting United into direct competition with Delta’s dominance, Kirby still isn’t allowed to play blackjack.

Before Scott Kirby became CEO of United Airlines, he was banned from blackjack tables across Las Vegas for counting cards. Now he’s applied that same risk-taking to one of the biggest bets in the airline industry.

When Kirby took over United in 2020, he wagered that customers would pay more for a better flying experience. The industry had long believed air travel was a commodity where only price and schedule mattered. Kirby disagreed. He ordered 270 new planes from Boeing and Airbus, reinstalled seatback screens that rivals had ripped out, struck a deal with Starlink for high-speed Wi-Fi and dumped the industry’s most-hated aircraft — the cramped 50-seat regional jet.

He seems to have hit the jackpot. United shares have doubled since early 2021, while most major U.S. airlines, except Delta, have seen their stock prices fall. Last year, Delta and United accounted for over 90% of the industry’s profits. But despite lifting United into direct competition with Delta’s dominance, Kirby still isn’t allowed to play blackjack.

Jonathan Small Founder, Strike Fire Productions

Entrepreneur Staff
Jonathan Small is a bestselling author, journalist, producer, and podcast host. For 25 years, he... Read more
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