CHICAGO- United Airlines (UA) CEO Scott Kirby built his career on calculated risks, but long before he led one of the world’s largest carriers, he was a serious blackjack player who taught himself to count cards.
A recent Wall Street Journal (WSJ) profile reveals Kirby remains banned from casinos across Las Vegas (LAS) to this day.
Under Kirby’s leadership, UA has undergone one of the most aggressive transformations in modern aviation. The carrier posted record revenue of $59.1 billion in 2025, and its shares have doubled since 2021. Together with Delta Air Lines (DL), the two airlines accounted for over 90% of the U.S. airline industry’s profits last year.
United CEO Banned at Casinos
Before entering the airline industry, Kirby spent time raking in money at casinos in Atlantic City and Las Vegas. He became skilled enough at counting cards that he was eventually banned from blackjack tables across the Vegas Strip.
The practice involves tracking which cards have been dealt to calculate the probability of favorable outcomes, one of the few methods that can shift odds in a player’s favor.
The WSJ recounts an incident at the Bellagio during Super Bowl week. Kirby walked in, handed over his ID to set up a line of credit at the high-limit poker table, and was promptly told by a manager that he could play poker or any other game, but not blackjack.
Kirby noted he had not played in at least 15 years but remained in the casino’s database.
Kirby now applies the same probabilistic thinking to running UA. He describes his approach as making decisions based on expected value rather than emotion. If the expected value is high enough, he can accept the outcome.
He draws a direct parallel between airline management and poker, emphasizing the need to know your own hand, read other players, and adjust strategy in real time.
The “United Next” Transformation Strategy
When Kirby took over as CEO in 2020, UA was in poor shape. The 2010 merger with Continental Airlines had been rocky, plagued by technology failures and labor disputes.
Former CEO Jeff Smisek was ousted in 2015, and his successor, Oscar Munoz, suffered a heart attack weeks into the role. Activist investors had taken aim at the company, and its reputation had suffered significant damage.
Kirby launched “United Next,” a five-year growth plan that involved ordering hundreds of new aircraft from Boeing and Airbus, retiring many of UA’s smallest 50-seat regional jets, and revamping the existing fleet.
The airline installed seatback entertainment screens on new planes at a time when competitors were removing them. It added power ports, larger overhead bins, and premium cabin configurations across the fleet.
A landmark 2024 deal with SpaceX brought Starlink Wi-Fi to UA aircraft. The airline reports the service is now installed on regional jets and will cover 50% of its mainline fleet by the end of 2026, with full fleet coverage expected the following year.
The carrier also introduced an upgraded business-class cabin with seats that fold into a couch-like configuration, improved wine selections, and invested heavily in its mobile app.
Features like Virtual Gate, which shows real-time boarding progress, and live TSA wait times powered by AI-enabled cameras have earned praise from frequent flyers and industry analysts alike.
Kirby’s Competitive Playbook and the Delta Rivalry
Kirby has long maintained that the U.S. market has room for only two successful premium airlines. His model draws direct inspiration from Delta Air Lines (DL), which proved over the past 15 years that passengers will pay more for a better product and stronger brand loyalty.
DL CEO Ed Bastian acknowledged UA’s efforts this month, noting they were smart to follow DL’s lead. Kirby fired back, stating he took initial inspiration from DL but has long since stopped copying the carrier.
UA’s premium strategy also includes targeting customers willing to pay for comfort over the lowest fare. The airline’s co-branded credit card program added over one million new cardholders for the third consecutive year in 2025, and its MileagePlus loyalty program now has over 130 million members.
The American Airlines Connection and Merger Proposal
Kirby’s career path adds another layer to the story. He spent years climbing the ranks at America West Airlines (HP), which acquired US Airways (US), which then merged with American Airlines (AA). Kirby served as AA’s president and was widely expected to become CEO.
When AA passed him over in 2016, UA hired him immediately. UA’s then-CEO compared the move to signing LeBron James.
Industry observers note Kirby appears driven in part by a desire to outperform his former employer. He recently pitched President Trump on a megamerger between UA and AA. American rejected the proposal, and Trump publicly dismissed the idea.
Analysts largely viewed the suggestion as characteristic of Kirby’s boldness, with many doubting that regulators would approve such a combination.
Operational Culture Shift at United
Beyond fleet and product upgrades, Kirby implemented internal changes that reshaped UA’s operational culture.
The airline eliminated its system of “delay codes,” which had previously assigned blame for every delay and created internal friction between departments. The change redirected energy from finger-pointing toward problem-solving.
UA also launched ConnectionSaver, a tool that identifies flights with enough schedule flexibility to be held for connecting passengers without delaying other travelers. The airline says the system has saved millions of connections.
Kirby pushed for greater transparency with passengers, instructing his team to share the same level of information with customers that they would share with him. Instead of pushing a flight back in 15-minute increments, UA now aims to provide realistic delay estimates upfront.
A High-Stakes Personality
Kirby reads for three hours daily, including biographies of Churchill, Lincoln, and Patton, along with decades of transcripts from competitors’ earnings calls. He takes a 20-minute nap at work every day and has seven children.
His aggressive style does not always work in his favor. The FAA recently imposed deeper gate cuts on UA at Chicago O’Hare (ORD) during a turf war with AA, and the merger proposal was quickly shut down.
At a global airline trade association meeting, Kirby looked around the room and told his peers that all airline CEOs crave the spotlight. The only difference, he said, was that he was willing to admit it.
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