The 10 Best And Worst Airline Leaders Of All Time—Southwest’s Genius, TWA’s Corporate Raider And American’s Decline

About 30 years ago I found Thomas Petzinger’s Hard Landing by accident in a Borders. It launched my fascination with the airline business. I’ve written about the book before. Recently, I was talking with a C-suite executive at a major airline and how badly that book needs an update, to bring in the last 30 years of the industry. We agreed the person who made the most sense to write it is former Wall Street Journal airline reporter Scott McCartney. That conversation, and reviewing old yearbooks from Conquistadores del Cielo, sent me down some rabbit holes thinking about the early figures in aviation, and the most consequential leaders not just in the U.S. but worldwide – who built the best airlines, who did the most damage, and who played their hands best? So I tried to lay out the 10 best and 10 worst airline leaders worldwide over time. The best, I think, was Southwest’s Herb Kelleher. What Counts As A Great Airline Leader? I’m looking at what someone did with the airline they had, and the opportunities available to them. Coming in to turn an airline around but going bust may be a heroic effort, and wouldn’t count against a top leader. Similarly, presiding over a profitable carrier doesn’t mean that leader created the conditions for success.: Strategy and results. Did the network, fleet, costs and product fit together to create a business that earned money over the long-term? Customers and employees. What did they deliver for customers, from fares to product, and what kind of culture did they build? Capital and staying power. What happened to shareholder equity? How did they deploy capital? What debts, commitments and competitive position did the next person inherit? Judgment in context. Government protection, subsidies, geography and luck count go into assessing achievement. So do self-inflicted failures and abuses of power. CEO, chairman or president doesn’t much matter here. Tim Clark’s title is merely president. I think he belongs on this list. Someone who borrowed a good idea may have leveraged it better than anyone else. Going bankrupt alone doesn’t make a leader the worst – they took on a challenge and failed. Rank Leader / Airline Why They’re Here 1 Herb KelleherSouthwest Low costs, low fares, loyal employees and a model that changed flying worldwide. 2 C.R. SmithAmerican Helped bring about the DC-3 and Sabre, changing the economics of running an airline. 3 Robert CrandallAmerican Combined loyalty, pricing, distribution and hubs into a formidable competitive advantage. 4 Michael O’LearyRyanair Made cheap flying possible across Europe at extraordinary scale. 5 Juan TrippePan Am Built global air travel and helped make the jet age and the 747 happen. 6 Tim ClarkEmirates Built a global connecting business around Dubai, large aircraft and a powerful brand. 7 J.Y. PillaySingapore Airlines Established a premium airline with commercial discipline despite no domestic market. 8 Richard AndersonDelta Used the Northwest merger, operational reliability and financial repair to set Delta apart. 9 Gordon BethuneContinental Made a broken airline reliable, profitable and a place employees wanted to work. 10 Pat PattersonUnited Built United into a major institution through decades of operational and employee investment. The ones who didn’t quite make it: Bob Six (Continental), C.E. Woolman (Delta Air Lines), Eddie Rickenbacker (Eastern Airlines), Lord Colin Marshall (British Airways), Donald Nyrop (Northwest Airlines), J.R.D. Tata (Tata Airlines became Air India), Albert Plesman (KLM founder) and Tewolde GebreMariam (Ethiopian). I could easily have swapped Patterson for Marshall or Six. 1. Herb Kelleher — Southwest Airlines Kelleher co-founded Southwest and fought the legal battles allowed them to fly – against an entire industry that tied their launch up in court for years – and served as its full-time CEO from 1981 to 2001. He made low fares sustainable – kept planes flying with quick turns, passengers deplaning out the rear while new ones entered from the front and flight attendants who still tidy the cabin between flights. They had a simple fleet, and didn’t add costs customers won’t pay for. The airline became known for peanuts (they stopped serving those in 2019), and those symbolized how frugal the airline was: other airlines served meals while Southwest served just peanuts. Some Southwest executives felt they needed to increase that investment and Kelleher shot that down, “Do you know what the difference in cost is between peanuts and Snickers?” Working with Colleen Barrett, he built an employee culture that helped make those economics possible. Kelleher, with his love of Wild Turkey and his back slapping ways, engendered a culture of fun. And the airline’s origin story, fighting against the odds against bigger airlines, created a sense of purpose. Customers got inexpensive transportation and employees who often seemed happy to be there. Southwest entered September 11, 2001 with $1 billion in cash and remained profitable that year without furloughs. In fact they made money for 47 consecutive years, from 1973 up until the pandemic. Southwest borrowed heavily from Pacific Southwest Airlines. That doesn’t diminish Kelleher any more than Ryanair borrowing from Southwest diminishes Michael O’Leary. Execution over decades earns the ranking. Here’s Bob Crandall’s retirement tribute: Then there’s the Just Plane Fun Southwest Shuffle, which he’s in – a parody of the 1985 Chicago Bears’ Super Bowl Shuffle. For everything that’s changed about Southwest Airlines since the days under Herb, employees at the airline still seem happy to be there. 2. C.R. Smith — American Airlines Smith ran American for most of the period from 1934 to 1968. If Juan Trippe deserves credit for pushing Boeing toward the 747, Smith deserves credit for pushing Douglas toward the DC-3 which revolutionized passenger travel. Working with American’s William Littlewood, he wanted an airplane that could carry passengers more economically. His commitment to buy it helped get it built. The DC-3 changed what an airline could earn carrying people, reducing its dependence on mail revenue. American moved from the DC-3 to the DC-7, which enabled nonstop transcontinental service, and then brought the Boeing 707 into service in 1959. He kept investing as the aircraft needed to compete changed. Smith developed major maintenance capabilities in Tulsa, established a dedicated flight attendant training college, and introduced the first airport lounge at New York LaGuardia and lanched Sky Chefs as a wholly-owned subsidiary to prepare meals for its flights. Smith also backed the enormous bet on computerized reservations that became Sabre. American needed to sell seats across a growing network without an army of people manually checking availability. Smith had political connections, and a Reconstruction Finance Corporation loan helped finance the aircraft purchase. He introduced FDR’s son Elliott to his second wife and was best man in his wedding, he also took a hiatus from running the airline to serve as Commerce Secretary in the Johnson administration. But his real legacy is in getting better planes built and making their seats easier to sell. 3. Robert Crandall — American Airlines Crandall, American’s president from 1980 and CEO from 1985 to 1998, found success in an integrated strategy that included marketing (AAdvantage as the first modern loyalty program), hubs, and yield management – which made the airline successful in the era immediately following deregulation. Crandall acquired Eastern’s Latin routes, which became long among the airline’s most profitable. He’s remembered for taking an olive out of salads to save money. He was cost conscious but understood when spending money created value for the business. Under his leadership, American became industry leader in selling, pricing and retaining customers. What’s most significant about Crandall is how the initiatives that grew under his leadership reinforced each other: American Eagle fed the airline’s hubs. The hubs let American profitably serve more markets. AAdvantage encouraged travelers to consolidate their flying with the airline. Sabre helped it sell the seats. And revenue management decided which fares to make available. His 1982 call urging Braniff’s Howard Putnam to raise fares was indefensible. They didn’t actually enter an antitrust-violating agreement. 4. Michael O’Leary — Ryanair O’Leary took the Southwest model and adapted it to a continent of national airlines, expensive airports and newly liberalized international routes. He became Ryanair’s CEO in 1994. He pushed harder on airport costs, aircraft deals, direct distribution and charging separately for things beyond the seat. He made airports compete for the airline’s business to obtain low costs. He bought aircraft when it was out of favor to do so and he could get better pricing – after the September 11 attacks Ryanair announced an order for 100 Boeing 737-800s. Ryanair made flying affordable on routes where people previously paid much more, took a long surface journey, or stayed home. It carries over 200 million passengers a year. And no one has his talent for getting free publicity, with claims like plans to charge to use the lavatory and new seats that will have passengers standing. He made ancillary fees support a very low headline fare. Baggage, priority boarding, reserved seats and other extras became substantial sources of revenue. Direct selling reduced distribution costs. Ultimately low fare carriers on the Ryanair model succeeded more in Europe than the United States, and have been copied throughout the world. 5. Juan Trippe — Pan American World Airways Trippe built Pan Am into the world’s best-known international airline. His ambition helped move aviation from flying boats to jets, and his commitment to the Boeing 747 helped make mass international travel possible. He thought bigger airplanes could lower the cost per passenger and expand the market. He helped build the physical infrastructure for international flying. Early long-distance service required much more than purchasing aircraft – he had to build operating bases, navigation capabilities, maintenance support and arrangements with foreign governments. Its Pacific flying boats depended on a facilities across remote islands. Trippe was organizing an international transportation system from the ground up. And Pan Am’s development of InterContinental Hotels gave passengers somewhere to stay at the destination. His political influence and privileged international position helped tremendously. They also left Pan Am vulnerable. Once airlines with domestic networks were allowed to compete internationally, they could feed their own overseas flights instead of just delivering passengers to Pan Am. Pan Am lacked a comparable home network, though it wasn’t for lack of trying. His efforts were rebuffed by regulators, but the airline’s success came through his political connections so when those don’t deliver that has to count against him too. A dozen years after Trippe retired, and two years into deregulation, Pan Am bought National Airlines in a failed attempt to buy that domestic route network. Pan Am DC-4, Credit: Ralf Manteufel via Wikimedia Commons 6. Tim Clark — Emirates Clark joined Emirates as part of its founding team in 1985 and became president in 2003. He helped turn Dubai’s location into a network that connects enormous numbers of city pairs with one stop. That required aircraft with the right range and capacity, connections, and a brand that persuaded people to choose Dubai over established hubs. Emirates made the A380 central to a business that made it the only airline to really make that plane work. Showers and an onboard bar created a halo for the entire airline. Emirates introduced personal video screens in every seat in every cabin in 1992, though – premium business travel, tourism, visiting friends and relatives connecting traffic, and cargo all contributed to the airline’s success. The airline had government backing but has also long been profitable. Ultimately he didn’t just build a global carrier and connecting hub in the desert, he helped put a nation on the world stage. 7. J.Y. Pillay — Singapore Airlines Pillay was Singapore Airlines’ chairman from its creation in 1972 until 1996. He helped establish the airline’s value proposition of aircraft, service and training, while delivering a commercially successful operation. And he did it with no protected domestic market. Singapore had to passengers to connect in Singapore and to pay for the experience. He doesn’t get credit for Singapore the way Lee Kuan Yew does, but he built the iconic Singapore Airlines brand that truly represents the nation. The company served Singapore’s national development, but the operating expectation was that it should win customers and sustain itself commercially. That distinction matters when so many national airlines became permanent claims on their governments’ budgets. 8. Richard Anderson — Delta Air Lines Anderson led Delta from 2007 to 2016, including through the Northwest merger. He helped turn the combined airline’s network and operational reliability into a business that travelers pay a premium for. In 2015, Delta recorded 161 days without a mainline cancellation, a 99.6% mainline completion factor and 85.9% on-time arrivals. He invested heavily in screens, line maintainence and wifi that customers could rely on and turned maintenance into a profit center. He bought cheap planes like used MD-90s and Boeing 717s, paired that with exceptionally strong maintenance capabilities, and generated strong investor returns. And he began paying significant profit sharing – $1.5 billion paid in his last year at the helm. Anderson acquired genuinely scarce network assets such as the deal of the century from Doug Parker’s US Airways taking over their New York LaGuardia position, and a 49% investment in Virgin Atlantic that improved access to London Heathrow. I was sharply critical of Anderson when he retired for rampant devaluations of SkyMiles devaluations and for his campaign to limit passenger choices and raise fares by advocating that the U.S. violate its Open Skies treaties with the U.A.E. and Qatar and block flights by those nations’ airlines. But, along with Glen Hauenstein and Gil West, he built Delta into one of the world’s most successful and admired airlines. 9. Gordon Bethune — Continental Airlines Bethune took over Continental in 1994 after two bankruptcies and years of damaged employee relations. His Go Forward plan became the business school benchmark for a turnaround and by 1995 the airline earned the largest profit in its history. He revamped the network, lowered debt, improved operational reliability and deepened employee engagement and profit sharing. He personally solved their immediate cash crunch. The former Boeing executive secured a $27 million refund of aircraft deposits. He killed the Continental Lite low fare airline-within-an-airline to concentrate on serving customers who were willing to pay for a dependable airline. Continental needed a schedule customers wanted to buy, an operation that delivered it, and employees who had a reason to care. Bethune bonused on-time performance, cut unprofitably flying, and insisted on a flyable schedule. 10. Pat Patterson — United Airlines Pat Patterson led United from 1934 to 1966, turning a collection of predecessor airlines into a large, dependable operation. His long tenure emphasized safety, passenger service and employee welfare, while taking United through enormous changes in aircraft technology and scale. He was a junior bank executive at Wells Fargo who approved a $5,000 loan for Pacific Air Transport in 1927, advised its founder and got to know the president of Boeing Airplane Company and Boeing Air Transport. He was recruited to Boeing in 1929, and became General Manager of United Air Lines in 1931 when it was formed out of the merger of Boeing Air Transport and other carriers. He became President when the Air Mail Act broke up Boeing, United and related companies. Patterson built the foundation of the current United with its acquisition of Capital Airlines. He transitioned the carrier from early transportation to a national jet airline, ordering 30 Douglas DC-10s in 1995. He made safety, dependability, passenger comfort, and sincerity explicit operating goals. He backed employee benefits and regarded employees and stockholders as equal partners. Under his leadership, United supported developments in airborne radar and instrument landing. In 1930, before becoming president, he approved Ellen Church’s proposal to employ nurses as flight attendants at Boeing Air Transport. The 10 Worst Airline Leaders In weighing the worst airline leaders, I had to look at the damage their leadership actually did. There were airlines that failed, but that doesn’t mean the CEO did a terrible job. Some inherited tough challenges and just couldn’t turn things around. For others, the nature of their business fundamentally changed with deregulation. The real question is what a leader did with the assets they had, and the condition they left the business in for their successor. Rank Leader / Airline Why They’re Here 1 Doug ParkerAmerican / US Airways Squandered American’s potential through network, product, fleet and capital decisions. 2 Kerry SkeenIndependence Air Turned a regional airline into a low-fare business saddled with high seat costs. 3 Philippe BruggisserSwissair The Hunter strategy tied a strong airline to a collection of weak ones. 4 Frank LorenzoTexas Air / Continental / Eastern Labor warfare and financial restructuring inflicted lasting damage across airlines. 5 Carl IcahnTWA Extracted value while debt, asset sales and ticket-discount obligations weakened TWA. 6 James HoganEtihad Tried to buy a global alliance through investments in airlines with failing economics. 7 Jeff SmisekUnited A badly managed merger, neglected customers and employees, and the chairman’s flight. 8 Vijay MallyaKingfisher Built a glamorous airline without sustainable finances, then compounded the problem with Air Deccan. 9 Chen FengHainan / HNA A sprawling acquisition binge left the aviation business entangled in a collapsing group. 10 Robin HayesJetBlue Loaded JetBlue with debt, lost ground to Delta in Boston, and pursued a doomed Spirit acquisition while experiencing a 70% decline in share price. The ones who didn’t quite make the cut: Jim Goodwin (United) and Bjørn Kjos (Norwegian). Goodwin’s United tenure deserves harsh criticism, especially the ‘summer from hell’ of 2000. Kjos’s long haul gamble at Norwegian was a disaster, but his real short haul achievement keeps him off this list. 1. Doug Parker — American Airlines Parker ran American from the 2013 merger with US Airways until 2022. He had the world’s largest airline, a newly restructured balance sheet coming out of American’s bankruptcy (which he arguably cut short by executing the merger), an extraordinary loyalty business and a brand with enormous potential. I don’t think there’s ever been an airline that underperformed its potential for longer than American Airlines under Parker. Capital. American spent $12.4 billion buying back shares through 2019, at an average $39.76, while adding debt. The airline entered the pandemic in a position of balance sheet weakness. It was loaded up with interest payments that hurt its financial performance. And it was capital-constrained when it needed to be investing in fleet and product to compete with Delta and United. Network. At US Airways, Parker traded the airline’s enviable New York LaGuardia position to Delta for Reagan National slots, cash and Brazil rights. Delta got an asset that helped establish its New York franchise, and Parker gave up something that could never be replaced and that kept American from matching the profitability of Delta’s credit card deal without relevance in the biggest spend market in the country. He later lost American’s close partnership with LATAM to Delta as well. Product. American squeezed more seats into planes, pulled out business class and extra legroom seats, and removed seatback screens – pursuing a cheap product without a low cost airline’s costs and right at the moment that customers were beginning in earnest to spend more money looking for a better product. He once remarked to employees that he never knew customers cared so much about food, and also that he thought he could get away with not investing in seat power. The airline is now spending to undo his mistakes. Fleet. Permanently retiring the 757s, 767s and A330s during the pandemic left American short of aircraft when international demand returned. The relatively young A330-200s made that decision especially hard to defend. And the airline’s lack of aircraft made it difficult to build back service in Chicago at the same time they were restoring Dallas and Charlotte. That nearly cost them their Chicago franchise, saved at the last minute by an FAA which blocked United’s growth at the airport that could have taken significantly more gates from them in the future. Employees. Parker’s supposed strength with labor (he convinced them to back the US Airways – American merger) didn’t produce an integrated East/West pilot operation at US Airways. He never managed to complete the merger of US Airways and America West until after the American merger. An employee survey in 2017 found that just 33% trusted his management to make the right decisions. He told flight attendants that they didn’t affect profit, as justification for not giving them profit sharing. And during the pandemic he furloughed more employees than any other airline CEO in history. Becoming CEO of the combined airline was a personal achievement after attempting to take over United, Delta and others along the way unsuccessfully. But he made the exact wrong decisions for the moment in the industry he was leading. And whereas other airlines saw their share price and market cap recover coming out of the pandemic, his didn’t. He destroyed $30 billion in shareholder value, which is more than any other airline CEO in history. Parker alienated shareholders, employees, and customers and he left American behind its major competitors, with deep debts, and an across-the-board need to fix its operation and product. 2. Kerry Skeen — Independence Air Everyone thought he was bluffing when he his Atlantic Coast Airlines wouldn’t come to a lower-cost contract to serve as a United Express carrier during the major airline’s bankruptcy. Skeen took the Washington Dulles-based airline and went out on his own in 2004 as an independent – Independence Air – with a high cost, low fare model. That doesn’t work. Atlantic Coast had a fleet of 50-seat regional jets with high costs per passenger, and enough of them that they simply had to offer too many routes and frequencies to fill. Then he made the seats hard to buy, initially relying only on the airline’s own website and in-house sales and refusing to pay for distribution through computer reservation systems. I criticized that while the airline was still flying. It was obvious even to me, even that back, that the model couldn’t work. (They eventually brought in Airbus A319s, but that wasn’t enough to save their economics.) They eventually changed course on distribution, but the larger economics were still broken. When Independence announced its shutdown in January 2006, fuel prices and United’s competitive response were convenient excuses. Skeen rejected major airline deals, and refused to sell the airline, taking it in to liquidation instead. Their failure was avoidable. He chose the strategy, had off-ramps he failed to take, but pushed ahead until he’d burned all the money. Credit: Frank Unterspann via Wikimedia Commons. Independence Air once intentionally loaded a mistake fare into their system for free publicity. 3. Philippe Bruggisser — Swissair As chief of Swissair’s parent, Bruggisser pursued the “Hunter strategy” recommended to him by McKinsey of buying stakes in other European airlines to create a major air group that bypassed bilateral negotiations between Switzerland and other European nations after Swiss voters rejected joining the European Economic Area in 1992. The problem was he spent too much, took on too much uncapped downside, and often obtained too little control in return. The liquidator’s investigation found CHF4.1 billion committed to investments in two years on airlines bleeding cash, done without clear financing. They got stuck covering losses at these carriers despite minority ownership. They acted as a “hunter” by acquiring minority stakes of 10% – 30% in smaller, high growth, and struggling European airlines like Sabena, TAP Portugal, and various French regional carriers. This was supposed to feed traffic from those airlines into their Zurich hub, to support Swissair’s long haul flying, making it an attractive ‘fourth’ European airline for a U.S. partner. They were going to keep their investments small, only they didn’t. And they became known as the ‘Flying Bank’ turning what was once a strong balance sheet into a disaster financed by short-term debt. Swissair had earned a reputation for financial strength. Bruggisser used it to buy a bunch of troubled businesses in order to serve more destinations within the group. He was removed in early 2001 and Swissair was grounded later that year. 4. Frank Lorenzo — Texas Air / Continental / Eastern Texas Air chief Lorenzo is hated by labor for using bankruptcy to tear up union contracts. He bought Texas International, Continental, Frontier, People Express and Eastern and launched New York Air. His consolidation and employee pay cuts created a poor operation. Eastern ended in a strike, bankruptcy, and eventual shutdown. He stripped Eastern of assets and moved them to affiliated companies. Its System One reservations business went to Texas Air, leaving Eastern paying him to use something it previously owned. Lorenzo pursued acquisitions faster than he could integrate operations. Folding People Express, New York Air and Frontier into Continental created service problems that burned customer loyalty and degraded the product. And his cost cutting never produced a financial turnaround, though Continental was briefly profitable before returning to bankruptcy as he left. 5. Carl Icahn — Trans World Airlines As TWA’s controlling owner and chairman, Icahn generated significant cash and burdened the airline with $540 million in debt. He sold London routes for cash and set the airline up to lose money after he left, with the 1995 Karabu ticketing agreement that allowed him to sell their tickets at a discount. He was able to purchase TWA tickets 45% below published fares (excluding trips beginning or ending in St. Louis) and re-sell them through Lowestfare.com,. That cost the airline $100 million a year and they were already struggling. TWA filed for bankruptcy in January 1992. Icahn exited as Chairman the next year, and TWA was back in bankruptcy in 1995 (and 2001, when it was acquired by American). 6. James Hogan — Etihad Airways Hogan ran Etihad from 2006 to 2017. The airline was mostly wonderful to fly, but pursued an expensive strategy that burned billions of dollars trying to build the Abu Dhabi hub. Under his leadership Etihad bought stakes in other carriers in order to redirect their connecting traffic through the U.A.E. Air Berlin and Alitalia were prime examples of his Swissair playbook. He gave them new uniforms and an upgraded product but both were financial basketcases. The airline lost as much as $2 billion a year by the end of his tenure. Here’s what he assembled: Airline Stake Air Berlin 29.21% Alitalia 49% Jet Airways 24% Virgin Australia 25% Air Serbia 49% Air Seychelles 40% Darwin Airline (rebranded Etihad Regional) 33.30% Aer Lingus 4.11 Etihad bought 70% of airberlin’s topbonus, 50.1% of Jet Airways JetPrivilege and 75% of Alitalia’s loyalty company. These investments poured more money into the airlines where foreign ownership restrictions limited the ability to inject more into the carriers themselves. Many of these investments went bad. airberlin and Alitalia entered insolvency in 2017. Jet Airways stopped flying in 2019. Hogan had access to extraordinary resources. He invested in product – like complimentary bus service for coach passengers and limousine service for business and first class, onboard chefs, and a prestige product of Apartments and Residences on their Airbus A380. Eventually though the spending was more than the Al Nahyan would fund. 7. Jeff Smisek — United Airlines Smisek led the combined United from 2010 to 2015. He had an extraordinary route network but screwed up the integration of the two airlines. He cut service and seemed indifferent to customers and employees. His safety-video promises of changes customers would like became a running joke. Project Quality was 1984-style Newspeak designed to chop $2 billion out of the airline. Oscar Munoz later got remarkable mileage from basics such as better coffee, stroopwafels, and showing up to listen to employees – giving a dejected workforce hope. Then there was the chairman’s flight: United launched a money-losing Newark – Columbia route to take the Chairman of the Port Authority of New York New Jersey to his vacation home in exchange for putting items the airline wanted on the agency’s agenda (things that might normally have been considered but that were held up without this payoff). Smisek had previously been Continental’s general counsel – he should have known the answer when personally asked for a bribe shouldn’t be “yes” but rather “excuse me while I call the FBI.” This all came out as part of the Bridgegate investigation. Smisek wasn’t criminally charged. United entered a non-prosecution agreement. David Samson pleaded guilty to bribery. 8. Vijay Mallya — Kingfisher Airlines Kingfisher founder and chairman Mallya launched the airline in 2005 with a premium product and plenty of glamour but could never make the finances work. His 2007 acquisition of Air Deccan added a low-fare airline to a premium one, with different customers, costs and service expectations. The deal was necessary to give them access to international flying under India’s bizarre rules at the time which created a domestic market bloodbath as airlines gained years of flying experience before being allowed beyond the nation’s borders, but the enlarged operation just accumulated more losses and debt while management struggled to decide what it was selling and to whom. By February 2012, only about 22 of its 64 aircraft were operating. Kingfisher stopped flying that year, and left employees unpaid and creditors pursuing what was left. The airline had deducted income tax from employee pay, but hadn’t actually sent the money to the government. Staff had been providing involuntary financing while at the same time working for free. Kingfisher was slated to join oneworld in February 2012, but that got put off and it never happened. The alliance still hasn’t found a partner in that market. 9. Chen Feng — Hainan Airlines / HNA HNA co-founder and chairman Chen built Hainan Airlines into a major Chinese carrier, and then pursued a global acquisition spree that bankrupted it. They accumulated interests across Hainan, Tianjin, Beijing Capital, Lucky Air, West Air, Fuzhou, Urumqi, Air Changan, Guangxi Beibu Gulf and Suparna airlines, along with Hong Kong Airlines and HK Express. Outside Greater China they bought stakes in Azul, Virgin Australia, Aigle Azur, Comair and Africa World Airlines. Their holdings extended to Swissport, gategroup, Servair, SR Technics, Avolon and the CIT aircraft-leasing portfolio. HNA invested in Hilton ($6.5 billion for a 25% stake), Carlson/Rezidor, NH, Red Lion, Pierre & Vacances, Dufry and Tuniu. And they bought into Deutsche Bank and Ingram Micro. Hotels, property, and various related and unrelated businesses – with over $150 billion in debt – created a group that was more financial engineering and vaporware than transportation business. And when that financing tightened, the underlying solid business found itself without any cash. HNA entered bankruptcy restructuring in 2021, and they ceded control of the airline three months later. Chen was sentenced to 12 years in prison for ‘harm to a listed company’ as well as fraudulently obtaining loans and misappropriation of funds. 10. Robin Hayes — JetBlue Robin Hayes took an airline with a product people liked, valuable positions in New York and Boston, and a reason for customers to choose it over competitors and left it struggling with poor reliability, too much debt, and a declining position in its best markets. He was CEO from February 2015 until February 2024. JetBlue hadn’t made money since 2019. A $100 investment in JetBlue at the end of 2018 was worth $35 at the end of 2023, which was less than half of what an average airline investment would have been worth. Hayes lost antitrust decisions both in his partnership with American Airlines and his attempt to acquire Spirit Airlines. Spirit made sense buying planes and pilots that would allow a defense of Boston and growth in Florida at the same time as growing New York with American Airlines slots. But once they lost the American deal, the strategic rationale for Spirit evaporated – but he decided to focus on pushing for Spirit instead of fighting for American. But Hayes agreed to pay $3.8 billion for Spirit’s equity, in a transaction valued at $7.6 billion including debt and leases despite being left with higher costs at Spirit and a plan to remove seats, sell fewer tickets, and incur capital expenses to retrofit planes. And it was clear that there was antitrust risk from the start – which is why JetBlue agreed to start paying Spirit shareholders before the deal closed and even if it didn’t get approved. JetBlue paid Spirit shareholders over $500 million to not get the deal. Delta overtook a distracted JetBlue in Boston. And they let let loyalty lag which is something Hayes even acknowledged, describing loyalty as a margin gap and said JetBlue was working to “play catch up.” The Hayes JetBlue wasn’t even a reliable airline. In fact, the Transportation Department imposed its first penalty ever against JetBlue for chronically delayed flights in the amount of $2 million for the June 2022 – November 2023 period. In the end, JetBlue has been a money-loser with nearly $9 billion in debt that’s been trying to reverse the mistakes of the Hayes era. Who Would You Put On These Lists? I’d especially like to hear from readers who love the business side of aviation. Who have I left out? Whose accomplishments am I underrating? And if someone belongs in the top ten, who comes off? I wanted room for Eddie Rickenbacker, Bob Six and C.E. Woolman at the top. A worldwide list made that impossible without leaving off people whose achievements I think were even greater. After I read Hard Landing, I went through every book in its bibliography. That led me to everything Robert Serling had written, and then to more books. I’ve gotten an enormous amount from this industry and the people who shaped it. Thirty years later, I’m still glad I happened to walk into that Borders.