Bob Jordan’s career at Southwest Airlines began with a hangover. Several hangovers, actually. Back in 1987, a 27-year-old Jordan arrived at Southwest’s Dallas Love Field headquarters to interview for a job as a computer programmer. The Indiana native, who’d spent his teen years in the Houston suburb of Spring and earned both a computer science degree and an MBA from Texas A&M, was working for Hewlett Packard in San Francisco, but he longed to return to the Lone Star State. “The day of my interview happened to be the day after everyone at Southwest had attended the corporate Christmas party,” Jordan told me on a video call in December. “Things were maybe just a little wilder back then.”

Indeed, they were. The company was then led by the chain-smoking, Wild Turkey–swilling Herb Kelleher, who knew how to inspire a good time in others. “Everybody I talked to that day looked awful,” says Jordan, who these days regularly lifts weights, runs, cycles, and does not smoke. “They were all hungover. The guy in the HR department who interviewed me was sitting in his chair holding his head the whole time. He finally passed me off to somebody else, whose face was green, and that guy passed me off to somebody in technology who asked me to fix an issue they were having. I went into the computer room and did some clickety-clickety and fixed it. They called me the next day and offered me the job.” 

Southwest has changed a lot since then. Its fleet and its workforce are both nearly eight and a half times bigger than they were in 1988. It’s hard to imagine that someone today would let an untested job applicant clickety-clickety his way through the company’s proprietary computer systems. And unlike Kelleher (who died in 2019), the CEO can no longer get away with wandering the hallways, lit cigarette in hand, kissing female employees right on the lips.

Jordan has changed a lot too. He arrived as a computer programmer with little management ambition, but he has gone on to hold fifteen titles with the company, including corporate controller, vice president of technology, and chief commercial officer. In February the silver-haired 61-year-old Jordan adds another: chief executive officer. Though not well-known outside Southwest before being named last summer as its next leader, Jordan has long been well-known and well respected at Love Field, especially by Gary Kelly, who has been CEO since 2004 and will now head the company’s board. “All the jobs I’ve had here came about because Gary said, ‘Hey, Bob, go do this,’ ” Jordan says. “Even if I didn’t have any experience, Gary would say, ‘You’ll figure it out.’ ” 

Jordan has a lot to figure out as he takes the helm. Arguably no Southwest chief executive since its first, Lamar Muse, has faced a more challenging environment on his first day. The sharp drop in air travel that followed the spread of COVID-19 caused Southwest to post a $3.1 billion loss in 2020, breaking the airline’s streak of 47 consecutive profitable years. Jordan will be charged with steering the carrier back into the black in 2022, but he’ll have to overcome a big obstacle: Southwest doesn’t have enough employees to fly everywhere it wants with the frequency it would like. That’s why the company is trying to hire 25,000 mechanics, flight attendants, pilots, and other employees over the next three years. That would be the biggest expansion in its history—if it can find all those workers.

At the same time, union leaders are grumbling that employee morale is low because of the pandemic and because, from their perspective, the airline is being mismanaged. The way they tell it, Southwest’s rapid growth in recent years has led to an erosion of the airline’s long-lauded culture of care for employees and customers. Passengers have complained too, especially after Southwest left tens of thousands of them scrambling for new travel plans when flight cancellations cascaded throughout the airline’s network on one particularly trying holiday weekend in 2021.

Southwest has been more consistently profitable than any other major carrier, has perennially ranked as one of the best employers in the country, and has consistently earned high satisfaction ratings from customers. But business pundits have prophesized for years that the onetime maverick company would face significant labor and operational difficulties as it got bigger. Still, the pandemic likely played an outsized role in fulfilling those predictions, and Jordan believes that the airline can right its course as the health crisis hopefully subsides. “There are a lot of things that just aren’t quite right at the moment,” he says. “But the company is not broken.” 

Jordan’s advantage in landing the top job at Southwest, company insiders say, was the extensive résumé he’d compiled there. “Bob grew up in the Southwest culture,” says Tammy Romo, chief financial officer and a thirty-year veteran of the company. “He exemplifies it. He’s got a tremendous heart. He loves engaging with people. He’s like Herb in that he’s never met a stranger.” 

It was once hard to imagine Southwest without Kelleher. It would be hard to imagine Southwest now without some of what’s been developed by teams led by Jordan. Those include Southwest.com, the company’s booking site, as well as Rapid Rewards, its loyalty program. Jordan also spearheaded significant changes to the company’s boarding procedure, leading to the A, B, and C groupings that passengers know today. But his most significant accomplishment may have been serving as president of AirTran Airways for three years after Southwest announced a merger with the Orlando-based carrier in 2011. Technically, Southwest won’t be the first airline Jordan has run.

That AirTran deal brought Southwest eight thousand new employees unfamiliar with its culture, along with dozens of new destinations, including its first international flights. Bringing the two carriers together involved intricate negotiations among multiple labor unions and the melding of corporate cultures. Romo says Jordan put in long hours meticulously working through dozens of complex issues, from unifying reservation system technologies to revamping pilot seniority lists. “If you see him in a meeting, Bob always has a notepad,” she says. “He’s very organized. He’s not a micromanager, but he makes sure things gets done.” 

Jordan emphasizes that the key to making that merger work was communicating often and effectively with employees. A lot of them. Mike Van de Ven, Southwest’s president, says that to this day, if you walk through the former AirTran hub of Atlanta with Jordan, “you’ll see that he knows a lot of people there because he was out in the field so much talking to everyone.”

Much more recently, when the pandemic hit, Jordan led an effort to cut thousands of workers from the payroll through “emergency time off” agreements and early retirements. Southwest was relatively generous with these packages, with voluntarily furloughed employees receiving half of their salaries, plus health coverage, for as long as eighteen months. (By comparison, American Airlines workers were eligible for just a third of their pay, plus as many as 350,000 frequent-flier miles and nearly two years of health benefits.) Some 25 percent of Southwest’s 60,000 staffers accepted some sort of package, and the airline’s total employment fell to 54,000. These moves allowed Southwest to avoid what would have been the first layoffs in its history and to save more than $1 billion in 2020, when its annual revenue plunged from $22.4 billion to just $9 billion.

But that money-saving program may be costing Southwest today. As demand for travel has rebounded, the airline is short on workers, a problem that’s not unique to Southwest. “The whole airline industry probably incentivized the retirement of too many people in certain key groups, including licensed mechanics and pilots,” says Robert Mann, an airline analyst with R. W. Mann & Company and a former executive at American Airlines. The problem with that for Southwest especially is that it began flying to many new destinations during the downturn and tried to serve them with fewer people while also maintaining most of its established routes. 

Southwest added eighteen cities to its network in 2020 and 2021, its most new destinations ever within such a short time frame. Kelly told me last spring that the idea behind that aggressive growth was “to put idle assets and idle employees to work” while generating revenue wherever Southwest could find it. But as travel demand roared back, Jordan says, the company found that with fewer workers, it wasn’t able to offer the frequency of flights that helps it make money and maintain reliable service. Indeed, the airline’s performance was dismal last summer, with just 62.4 percent of its flights arriving on time in June. That was down from 81.3 percent in May, a number that’s more typical for Southwest. Many carriers saw drops in on-time arrivals as travel demand boomed in the summer, but Southwest’s 19 percent falloff from May to June was bigger than the declines at American, Delta Air Lines, and United Airlines.

Southwest also canceled an average of 2.7 percent of its flights from June through September 2021, while U.S. carriers as a whole canceled just 1.95 percent of flights. Then things got worse. Over Columbus Day weekend, in October, a brief shortage of air traffic controllers in Jacksonville, combined with military-related airspace closures and thunderstorms around Jacksonville and Orlando, resulted in a ground stop for all flights. Other carriers soon recovered, but Southwest’s network melted down as crews and planes were out of place. Jordan says roughly half of all Southwest flights touch down in Florida on any given day, and when the disruptions happened, about seventy planes never made it to their intended destinations, causing a ripple effect across the network. To reset its system, the company canceled 2,500 flights over four days. 

While Jordan sees no chance of a repetition of that series of unfortunate events, the union representing Southwest’s pilots blames long-standing operational dysfunctions for the mass cancellations. The union has been lobbying for years for Southwest to upgrade its IT system and change the way it responds to service interruptions, such as a storm system that grounds flights. “Watching the meltdown that occurred over Columbus Day, after telling management for years that something like this was going to happen, was frustrating,” says Casey Murray, president of the Southwest Airlines Pilots Association.

The unions argue that the people-first culture the airline has promoted since Kelleher’s era has suffered. Management, they say, has in recent years focused more on serving shareholders and on getting bigger than on employee engagement, which is, in turn, key to customer satisfaction. “There’s been so much growth there that it is now harder to have this pro-employee, friendly environment,” says Lyn Montgomery, president of TWU Local 556, the union representing Southwest’s flight attendants. “It’s just been moving toward a bigger corporate approach. If things don’t change, we’re going to see more attrition.” 

Still, both union leaders say they’re cautiously optimistic about Jordan’s ability to make changes, in no small part because, as Murray says, “Bob is a people person, and I think that’s fundamentally different from Gary Kelly.” 

Jordan spent the summer, fall, and early winter hopscotching across the Southwest system, talking with employees in large groups and individually as he walked through airports and boarded planes. In the typically hokey Southwest corporate style, delivered with an accent that melds the Midwest with southeast Texas, Jordan says his objective was to “love on” the workers, most of whom, he believes, still view the airline as a great place to work. He admits, though, that he’s heard complaints—about the job getting harder during the pandemic because of mask mandates and unruly customers (some of whom have assaulted flight crews) and about the company asking too much of its workers in an already stressful environment. To the complaints, he’s responded with contrition. “I think it’s important to apologize,” he tells me. “We’ve had people who’ve worked a mandatory eight Saturdays in a row. I thank them for doing that, and I say, ‘My apologies that we put you and your family in that situation.’ And now it’s my job to do something about it.”

His first objective is to hire those 25,000 new employees during the next three years, to relieve thinly stretched staffers and boost operational reliability. But hiring isn’t easy for any company right now, not even Southwest, which has landed on Forbes’s “Best Employers” list for the past six years. Before the pandemic, the company averaged 42 applicants for every open job. Today, it’s getting only about 14. It needs more workers in every category—pilots, flight attendants, gate agents, plus the people who handle all those bags that fly for free. 

At the same time, it’s adding new planes, including 28 last year and as many as 114 this year (while retiring more than 30 old jets). Last year’s additions were deployed to serve the eighteen new destinations that Southwest started flying to during the pandemic. This year’s new planes will enable Southwest to boost the number of flights it offers nationwide, ideally resulting in fewer delays and cancellations. With more-frequent flights, there’s less chance of stranding passengers and crews. 

New routes and new planes cost money, and Southwest’s costs have crept up in recent years. Mann says Southwest, which was once able to operate more cheaply than almost all its competitors, is now squeezed between carriers such as American, whose international routes make it a much larger airline, and Spirit Airlines, a smaller, no-frills carrier that maintains ultralow operating costs. Mann and other industry analysts think that cost creep could become a permanent problem for Southwest, whose stock lost nearly 5 percent of its value in 2021, even as the airline announced in December that it expected to post a fourth-quarter profit and to remain profitable in 2022.     

Jordan’s priorities begin not with profits (although profits are on his list) but with people—both adding more and taking time to recognize the two turbulent years that employees have just endured. It’s easy to imagine Herb Kelleher approving of that approach. “Your people come first,” Kelleher often said, “and if you treat them right, they’ll treat the customers right.” Still, Jordan is no Kelleher, nor will he try to be. “I tell people in leadership training,” he says, “that it’s hard enough to be a leader as yourself without trying to be a leader as somebody you are not.”

Which is not to say Jordan won’t do some things just as his predecessors have. He has already kept the tradition, begun by Kelleher, of dressing in elaborate costumes on Halloween. He has shown up as Ken, of Ken and Barbie, as well as a mop-topped George Harrison and a young Luke Skywalker. And, like Kelleher, Jordan is a whiskey drinker, though he prefers his mixed into a Manhattan.

That’s a somewhat recent development. Back in 2008, Jordan employed another form of liquid courage, one of his favorite cocktails, before he shaved off a mustache he’d sported for three decades. That drink: a cosmopolitan. “I wish I could say that’s a vicious rumor,” Jordan says, laughing. “But no, it’s true.”

Joseph Guinto, formerly the editor in chief of Texas Business magazine, is a freelance writer and editor based in Washington, D.C.

This article originally appeared in the February 2022 issue of Texas Monthly. Subscribe today.