By Alison Sider and Ben Cohen
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.
Until recently, the industry believed that air travel was a commodity -- that customers only cared about price and schedule. But that's wrong, Kirby says. The experience matters, too, and he's now convinced that a better one can earn brand loyalty.
"I always thought this would work," Kirby said this past week at United's Chicago headquarters. "Even I have been surprised at how much difference you can make by investing in all of those things."
It's also making lots of money. United shares have doubled since the start of 2021, when every other major U.S. airline besides Delta watched its stock fall. Last year, Delta and United accounted for over 90% of the industry's profits.
For more than a decade, Kirby has insisted that the U.S. only has room for two successful premium airlines. To make sure his airline would be one of them, he outlined a growth strategy five years ago that he called "United Next." His plan involved ordering hundreds of bigger jets from Boeing and Airbus, dumping many of United's smallest regional jets and revamping the airline's existing fleet with seatback screens, power ports and more spacious overhead bins.
"The more we invest," he said, "the more we win."
The audacious CEO has such grand ambitions for United that he recently pitched President Trump his boldest idea yet: a megamerger with American Airlines.
Before American rejected the proposal and Trump publicly shot down a potential deal, airline officials dismissed any merger as impossible to get past antitrust enforcers -- and typical bluster from Kirby. Some even speculated that he was out for revenge against American, where he was a rising star until he was passed over for the top job. Whether or not it ever happens, the idea alone was so brash that the industry agreed that it could have come from only one person.
Love him or hate him, everyone in the business is deeply obsessed with Scott Kirby.
Not long ago, Kirby was at a meeting of the global airline trade association, he told the Airlines Confidential podcast, when he looked around the room full of his peers and stated the obvious.
"All airline CEOs crave the spotlight," Kirby said. "The only difference between you and me is I'm willing to admit it."
A strategy is born
Kirby, 58, grew up in a small town outside Dallas, went to the Air Force Academy with dreams of being a fighter pilot and ended up with a much different career involving planes.
After studying computer science and operations research, he interviewed for quant jobs on Wall Street but decided he couldn't possibly live in New York. He moved back home, joined a wonky subsidiary of American Airlines and applied his mathematical brain to pricing airplane seats.
In the mid-1990s, he jumped to America West, where the strategy was keeping costs as low as possible. America West bought US Airways, which merged with American Airlines, and Kirby became the president of what was then the world's biggest airline. He was widely considered to be in line to be CEO until American decided in 2016 that he wasn't the right guy -- and United snapped him up. United's CEO at the time said it was like signing the LeBron James of the airline business.
But when Kirby took his talents to United, the airline was in rough shape.
United's merger in 2010 with Continental had been a turbulent process beset by tech snafus and labor disputes. In 2015, CEO Jeff Smisek was ousted. His replacement, Oscar Munoz, suffered a heart attack weeks into the job. By the time he recovered, activist investors had taken aim at United and the company's reputation was in tatters.
As United was struggling, Delta was reorienting itself -- and the entire business -- around a radical idea: that people would pay extra to fly their airline of choice.
At the time, airlines believed that travelers generally picked the cheapest flight that worked for their schedule. Delta made another wager: If it offered a better product, it could command higher prices.
"This is not soybeans," former CEO Richard Anderson once said.
Delta is now the most profitable U.S. airline. Instead of shopping around for lower fares when they book, its legions of fans just open the Delta app. Delta fliers swipe its co-branded American Express plastic so often that spending on the cards approaches 1% of the U.S. gross domestic product.
Kirby believes there are more customers willing to pay up for premium seating than anyone realized. The problem was that only Delta was offering a product they wanted to buy.
Now the entire industry is targeting fliers who prioritize comfort. Despite the competition, Delta keeps powering ahead. With every new amenity, it's sending rivals a message: good luck catching up.
"I think they're smart trying to copy us," CEO Ed Bastian said this month.
This week, Kirby fired back: "I did take inspiration from what Delta has done. But we long ago stopped copying them."
The premium economy
Kirby once dismissed live TV on planes as a gimmick, then he saw how they changed the flight experience at JetBlue. He started as a fierce critic of American's premium-heavy cabin configuration on cross-country flights until data showed the appetite for it. Before he poured money into United's selection of wine, he was a staunch defender of US Airways charging passengers for water.
"I can do 180 degrees in a second," he said. "If the evidence changes, I can change my mind."
But splurging on upgrades didn't come naturally to executives accustomed to agonizing over drops of fuel.
At first, his airline was still firmly in that commodity mindset. During a cost-cutting effort called "Project Quality," it had eliminated in-flight ketchup from some flights. In 2017, one executive wondered why United bothered serving food at all. When he took over as CEO in 2020, Kirby realized that United would have to spend its way back into competition -- and he knew where to start.
To Kirby and Andrew Nocella, a revenue guru he recruited from American, many of United's problems could be traced back to the industry's sorriest plane: the 50-seat regional jet.
Customers hate the tiny, cramped metal baguettes that feed passengers from small cities across the country to major hubs. They typically don't have Wi-Fi or enough space in overhead bins to fit a full-size roller bag. Most importantly, they don't have business class seats.
With the airline losing market share, United's top executives decided: We're going to need some bigger planes.
In 2021, they placed the airline's largest ever order for 270 single-aisle planes from Boeing and Airbus, followed the next year by 100 narrow-bodies and at least 100 wide-body Dreamliner jets for international routes.
As airlines ripped out screens for seatback entertainment to make planes lighter and cheaper, since everyone had their own phones and tablets, Kirby put screens back on planes, convinced that their mere presence made a huge difference.
"We could easily and quickly distinguish United as a premium brand," said Nocella, United's chief commercial officer.
Even more impressive is Wi-Fi that actually works. For business travelers, the ability to answer emails from 30,000 feet is no longer a luxury but a necessity. So in 2024, United struck a deal with Starlink to equip its planes with the industry's fastest Wi-Fi. The service has been installed on regional jets and United says it will be on 50% of its mainline fleet by the end of the year and 100% next year. (Until then, you're stuck fighting spotty internet from Newark to San Francisco.)
Meanwhile, Kirby keeps pressing executives to improve the experience of flying United, repeating one phrase that has become a mantra: "Your job is wow."
"They all looked at me, like, what the hell does that mean?" he said.
It means he wants customers to think: "Wow, I've never seen an airline do this."
By now, everyone at the airline is used to Kirby's personality. His route planners know not to let him in on splashy new destinations too far in advance. He has trouble keeping them secret.
Kirby likes to read biographies of Churchill, Lincoln and Patton -- and several decades of transcripts from rivals' earnings calls. But his aggressive style doesn't always work in his favor. This week, the FAA intervened in a United vs. American turf war for gates at Chicago's O'Hare Airport and hit Kirby's airline with deeper cuts. Then his suggestion of a merger was swatted away by Trump, the latest reminder that Kirby can overplay his hand.
United takes flight
Early in the airline's transformation, United launched a tool called ConnectionSaver, which identifies flights with enough wiggle room to be held for passengers racing to make their next leg without delaying everyone on board. United says it has saved millions of connections for customers -- and saved employees from slamming the door on them.
But it was another change that executives hail as the most consequential of them all.
"Removing delay codes," said David Kinzelman, United's chief customer officer, "is probably the single greatest cultural shift."
Before that shift, the airline doled out blame with a code for every possible cause of a delay. "We would argue for hours about a one-minute delay," Kinzelman said. Now, instead of pitting teams against each other, United spends that time figuring out how to solve the problem.
It's giving passengers more clarity, too. Every frequent flier recognizes the frustration of flights getting pushed back 15 minutes, then another 15 minutes, knowing it will take a full hour to find someone to repair that broken toilet. United's fix: just say it's probably going to be an hour.
Kirby told his team to pretend he's on the plane and demanding information -- and then give passengers that information.
"Why can't we just tell customers everything that you would tell me?" he asked.
Kirby has piled hundreds of millions of dollars into modernizing United's tech and improving its app, heralded by aviation geeks and airline executives as the best in the business. One popular feature of the app is Virtual Gate, which shows precisely how many people have boarded. And when security lines snaked through terminals during a partial government shutdown last month, United spotted an opportunity to introduce live TSA wait times. It's now installing AI-enabled cameras in airport lobbies to collect the data and monitor queues in real time.
The way Kirby sees it, moves that look risky to others are safe bets.
"The truth is," he said, "I have a different view of risk than most people."
He prides himself on thinking probabilistically and making decisions based on expected value. If the expected value is high enough, he can live with the outcome. "I don't mind losing a hand," he says. To him, running an airline is like the highest-stakes version of a game that casinos still let him play: poker. "You've got to know your own hand, know the other players and constantly adjust how you play," he said.
But when he likes his cards and bets accordingly, Kirby doesn't even consider it gambling.
"I don't actually gamble," he said. "I do smart, expected-value things."
Write to Alison Sider at alison.sider@wsj.com and Ben Cohen at ben.cohen@wsj.com
(END) Dow Jones Newswires
April 24, 2026 21:00 ET (01:00 GMT)
Copyright (c) 2026 Dow Jones & Company, Inc.
Comments