Forever Herb

There’s only one proper way to pay tribute to the iconic Founder of Southwest Airlines: through stories from those who knew him best.

The most famous “only Herb Kelleher would do that” story starts in the marketing department. Southwest Airlines introduced the slogan “Just Plane Smart” in the early 1990s. After Southwest used it for a year or so, officials from Stevens Aviation, an aircraft sales and maintenance company in South Carolina, protested that they had already been using “Plane Smart.” 

A lawsuit seemed imminent. But instead of duking it out in the courtroom, Herb and Stevens chairman Kurt Herwald came up with a novel solution: an arm-wrestling competition for the rights to the slogan. As Southwest’s Chairman, President, and CEO, Herb rented out an arena, gave Employees time off so they could attend, and turned the entire event into a low-brow, high-comedy showdown worthy of the professional wrestlers who joined him in the ring. 

Southwest’s PR department chronicled Herb’s “training” before the match. He did off-rhythm jumping jacks alongside Employees doing their best not to laugh, curled a barbell made out of empty bottles of whiskey, and summited a flight of steps as if it were Mount Everest.

When the fateful day arrived, “Smokin’ Herb” Kelleher did battle with “Killer Kurt” Herwald in the “Malice in Dallas.” Wearing a white boxing robe and red athletic shorts over gray sweatpants, Herb strutted to the ring, a cigarette dangling from his lips. Flight Attendants dressed as cheerleaders chanted his name. His arm in a sling, Herb claimed to have hurt it rescuing a child from traffic on the way to the arena. He read a faux proclamation from then-Texas Supreme Court Justice John Cornyn demanding that Herb be replaced by a former Texas arm-wrestling champion. 

And on and on. 

When it was over, Herwald “won” the best-of-three competition … and then said Southwest Airlines could use the slogan after all. The companies raised $15,000 for charity, and both companies got more publicity than they could have imagined. Herb’s reputation as a masterful and unconventional leader soared. Even President George H.W. Bush sent Herb a letter declaring the whole shebang “Just Plane Terrific.” 

That incident encapsulates what made Herb an icon. It was a little bit crazy and a little bit brilliant—and totally Herb. Southwest’s Founder, who died on Jan. 3 (he would have turned 88 on March 12), led the Company from an idea on a cocktail napkin to the largest carrier in America in passengers served by combining an ingenious business mind with an unending desire to treat people well and a refusal to take himself or life too seriously. 

“He is truly a legend, truly one of a kind, truly larger than life,” says Gary Kelly, the current Southwest CEO who worked for and was friends with Herb for three decades.  

Herb (he insisted everyone call him that) liked to describe Southwest as a mosaic made of many different parts. He was the same way. It seems like a contradiction that a man who wanted to have so much fun in everything would also be a tactically savvy lawyer, a hard-nosed businessman, and a highly focused leader of a Company renowned for its fiscal discipline. But not if you listen to the stories from the people who knew him best. No less an authority than Kelly once marveled at these diverse traits. How could a single individual have all of them? He came to a simple conclusion to explain their presence in one person. 

“It’s the magic,” he says, “of the word ‘and.’” 

Herb through the years: (from left) as a young boy growing up in Audubon, New Jersey, circa late 1930s; as a lawyer about 20 years later; on the job after being named interim Chairman, President, and CEO of Southwest Airlines in 1978

He saw everyone the same
—as people 

“We hire great attitudes, and we’ll teach them any functionality that they need.” — Herb Kelleher

Colleen Barrett and Herb worked so closely together for so many years—51 in all—that some people came to refer to them almost as one person: Herbandcolleen. Barrett sees the success of her career as proof of Herb’s unique ability to see beyond a person’s apparent station in life and to lift them higher than they would have otherwise reached. When they first met, at a law firm in Texas where Herb was a lawyer, Barrett was a legal secretary assigned to another attorney. By the time she retired in 2008, she was President of Southwest Airlines. 

“Here I am, a little girl from the sticks of Vermont who didn’t know anything. He treated me as an equal from the day he met me,” she says. “That’s the way he was with every single Employee or friend he ever met.”

Herb’s philosophy at Southwest was to hire for attitude, not experience, and Barrett’s success validates that approach. At that law firm, when the two began working together, Barrett’s first task was to organize Herb’s office. He actually had two offices, an empty one in which he met with clients and another that was overrun with documents. His filing system, if it could be called that, was to scatter papers around the room. 

“It was the worst thing I ever saw,” Barrett said, laughing, in January during a “celebration of life” service honoring Herb.

She attempted to instill order while he was on vacation. She was worried that when he got back, he would ask for something, and she would not be able to find it right away, and that would be the end. But he asked, she found, and from there, a relationship that would change American aviation blossomed. 

Barrett accompanied Herb to court, to lobby in Washington, D.C., and to political meetings in Texas. Often, he had to pick her up and take her home because poor depth perception left her unable to drive. Countless times, she saw Herb’s unique personal touch, either with her or other people. “He was brilliant,” she says. “But he was also kind and never thought he was better than anybody else.”

Once, the two attended the funeral of a man they knew. They did not know the man’s wife, and she stood alone during the service. No family members held her, no friends comforted her. As the preacher spoke, the woman cried uncontrollably, shaking with grief.

“Herb walked up and held her as if she was his daughter,” Barrett says. “She sobbed and sobbed. She had her head on his shoulder. He led her away as if he had brought her to the cemetery. It was so him. And he didn’t think there was anything unusual about it.” 

He let Employees be themselves 

“Your People come first, and if you treat them right, they’ll treat the Customers right.” 

No one made Herb laugh harder than Carroll Herzog,  a 40-year veteran of the Company who works in Customer Service at Hobby Airport in Houston. The stories she tells reflect the Culture that Herb built that allowed Herzog to be herself and underscore how the Company took on his personality.

Shortly after 9/11, Herzog and her fellow Customer Service Agents were tasked with searching Customers’ luggage. It made everyone uncomfortable, Employees and Customers alike. Herzog went out and bought an enormous pair of white cotton underwear and a red garter belt. She stashed them behind the counter, and every once in a while, she would hold one or the other up in front of unsuspecting Customers whose luggage she was searching and ask, “Is this yours?”

Another time, a businessman was annoyed that he had bought a nontransferable ticket. He wanted it to magically become transferable, and he expected Herzog to make it so, and he didn’t want to pay for it. She wanted to help but told him she couldn’t do that. Speaking right in front of her, he muttered that she must have PMS. She quickly fired back, “Yes, I do: profit motivated syndrome.”

Herb laughed again and again at those stories. They weren’t just funny; he thought they represented good business practices and modeled what he wanted Southwest to stand for. Herb, who in 1978 elevated from Southwest’s corporate counsel to Chairman of the Board and permanently became President and CEO in 1982, insisted Employees should come first and that the Customer isn’t always right. Empowered by the knowledge the boss had their back, Employees would treat Customers well. Those satisfied Customers, in turn, would become repeat Customers, which would please the Shareholders. 

Herb also believed that making smart decisions was more important than following rules to the letter. He wanted creative risk-takers, not automatons. More than anything, he wanted Employees to have fun at work and Customers to have fun on his planes. A rigid adherence to, say, line 23, subsection E, paragraph 90, would squelch that. So instead of some 500-page Employee manual, Southwest produced 30 pages of “guidelines.” 

“You know what the first line was?” he said in a 2017 interview with the San Antonio Public Library. “‘Guidelines for leaders: These are only guidelines. Feel free to break them in the interest of our Customers.’ And our People did. They were, I think, somewhat apprehensive at first. They didn’t believe we really wanted this kind of world. But after six months or a year, they were into it, big time.”

That attitude became the foundation of the Southwest Culture. That Culture was created by Herb and Barrett based on the Golden Rule—treat others as you’d want them to treat you—something both learned growing up. 

Even as Southwest grew, the Company never lost its sense of humor, because it kept hiring people like Herzog. Whenever Herb flew through Houston, he would show up at Herzog’s counter with a new friend and ask her to retell the PMS story or the underwear story or another crazy story she had, and laughter would explode out of him like confetti from a cannon. “He always wanted everybody to think they were the greatest, and he wanted to bring the greatest out in everybody,” she says. “That’s such a gift. You didn’t even realize that’s what he was doing when he was doing it. That’s how good he was at it.”

In 1994, Pilots gave Herb a custom Harley-Davidson.

His laugh roars on 

“What we are looking for first and foremost is a sense of humor.” 

Herb’s laugh was a legend in itself. “It wasn’t just loud,” says Bill Cunningham, presiding director of Southwest’s board of directors. “It was a vivacious laugh, a big laugh.” 

Ron Ricks, the vice chairman of the board, describes it as “incredibly infectious.” 

It’s immortalized at Southwest’s Dallas Headquarters. On one wall, there’s a button, and when you press it, you can hear that unmistakable sound: full-bodied, booming, genuine. 

Terry Maxon, who covered Kelleher and the airline industry for more than 20 years for The Dallas Morning News, says he once thought of trying to turn Herb’s laugh into a ringtone. 

“But it would have scared people, I think,” he jokes, adding that Herb’s laughs kept going until he ran out of air. “Everybody knows they’re not that funny,” he says. “But with Herb, you thought, Maybe I am that funny. He just made people feel good about themselves.” 

Herzog adds: “He’d hock up a lung he was laughing so hard. Who has a laugh that makes you laugh when you’re just talking about his laugh? Nobody, except for him.” 

He had a remarkable
memory …  

“Show [people] that you admire, value, and love them as individuals, rather than just as ‘producers.’”

When Maxon started covering the airlines for the Morning News in 1990, he scheduled a meeting with Herb and Barrett. Maxon wanted to introduce himself and put names to faces and let them do the same. 

“I said, ‘It’s a pleasure meeting you, Mr. Kelleher,’” he says. “He said, ‘But we’ve met before.’ Herb and Colleen marched me down to the lobby in the headquarters to show me a framed story they had down there that I had written probably a decade earlier when I was covering Dallas City Hall. I had forgotten, but they had not.”

Maxon had written hundreds of stories in between, so it’s not surprising that he forgot. But Herb had met thousands of people over that same time, so his recollection stunned Maxon. “I don’t know how he did that,” he says. “But it wasn’t fake. He did not have a team of 100 people hiding in the room behind him whispering in his ear.” 

Many of the tributes that have poured in recounted similar stories of his uncanny ability to recall names and details, even involving people he met only once before. 

“When I first met him, I thought [his memory] was some trick. Not that it was disingenuous, but a trick that he had some sort of book or guide that he would go refresh his recollection,” Ricks says. “No. It was real. We’d go to Washington. We’re walking in the halls of Congress. He’d remember the name of a young staffer who he had met a few years ago. Most CEOs wouldn’t even say hello to a young staffer. Herb remembered their names. I was always very jealous of that skill.” 

Herb loved his Southwest Family, which included CEO Gary Kelly and President Emeritus Colleen Barrett (above).

… but it wasn’t perfect 

“I forgive all personal weaknesses except egomania and pretension.”

These same friends who marvel at Herb’s photographic memory also laugh at his absent-mindedness. He could be oblivious—to what day it was, what time it was, where he was supposed to be. It was not uncommon for him to have one lit cigarette in each hand, apparently because he forgot about the first one. He lost his car keys, his rental car keys, and even cars. Barrett says Herb once paid a cab driver $200 to drive him around the Dallas airport looking for his car. Another time, Herb arrived at the airport in San Antonio. He saw someone he knew, screeched to a stop, jumped out of the car, and started talking. Hours later, he was in Dallas when he got a call from someone at the San Antonio airport. 

“Did you get a new car?” the person asked. 

“Yes,” Herb said. 

“Is it a silver Mercedes?” the person asked. 

“Yes, why do you ask?” Herb said.

He had left it running in front of the airport.

His on-time arrivals were
a challenge

“Think small and act small, and we’ll get bigger. Think big and act big, and we’ll get smaller.”

Kelly, Barrett, and Ricks traveled with Herb extensively. Everywhere they went—Southwest Headquarters, restaurants, airports—he stopped to talk to people he knew. He would not, could not, walk by an Employee without saying hello. Ever. He often hugged and/or kissed most of them, too, and whoever that person was, Herb made him or her feel like the only person in the room. 

Meetings, appointments, and flights were constantly in jeopardy as a result. These impromptu conversations happened so often that Herb’s friends had a routine to try to get him to his next meeting or flight. “Go get him,” Barrett would say, and dispatch Ricks or Kelly or someone else to intervene and retrieve Herb by physically standing between him and whoever he was talking to. 

“Most of the time, he would fuss at the person who came to get him. Like, ‘I’m talking to this person,’” Ricks says. “That was more important to him than the flight, the speech, the meeting. You would literally have to interrupt and tell the person, ‘I’m sorry. Herb’s going to miss his flight.’ He would not break away.”  

He could warm up any room 

“Southwest’s essential difference is not machines and ‘things.’ Our essential difference is minds, hearts, spirits, and souls.” 

Stories abound of Herb’s phone calls, handwritten letters, and visits to Employees and friends who needed a boost. He believed in the power of the personal touch, though he probably wouldn’t have put it that way, because that implies forethought, when he usually just acted on instinct. “He loved to serve,” Barrett says. “I told him one day, ‘You are the best servant-leader I have ever met.’ He literally said to me, ‘What the hell is that?’ He looked at me like I had three heads.”

Herzog relays one sobering memory. One day, a pair of sisters who worked at Southwest were walking through the lobby of a Houston hospital. They saw Herb talking to a couple of men in suits. They didn’t want to bother him. But he saw them, hollered hello, and came over to talk. They told him they were there to visit their mother, who had just gotten bad news about cancer. 

“He goes up to their mother’s room and introduces himself as Dr. Kelleher and proceeds to tell their mother how important they are to the airline, and they could not be Southwest Airlines without them,” Herzog says. “When I tell that story, I get reduced to tears. I could never imagine being able to do that. Going into a hospital room is hard enough for a family member. To be able to walk in there and totally change the energy of the room—he was fearless. Not only was he funny, but he was just so genuine. It was so easy for him.”

Many anecdotes about him begin something like, “He didn’t have any reason to be nice to me, but …” That’s how Dallas entrepreneur Craig Hall starts his story. In the mid 1980s, Hall’s real estate empire was crumbling. “A lot of fair-weather friends stopped calling or returning my calls,” Hall says. “In the midst of all that, Herb calls and spends time with me and takes me to dinner. He was there when nobody else was there. That’s a side of him that a lot of people probably don’t know.”

Hall spoke at the celebration of life service wearing one of the hideous ties Herb had sent him over the years as a running joke. Herb often sent Hall handwritten notes, too. “In addition to his bombastic facade of great humor and his great laugh and all of that, there was a real compassion and a real decency of the human spirit that few people have,” Hall says. 

The Hall story is one of Barrett’s favorites. She says that when Southwest was starting out in the early ’70s, Herb and other Company officials were shunned by the Dallas business community. Barrett believes that’s why Herb empathized with Hall: He wanted to do what nobody did for him. 

Whether he was serving Customers snacks onboard, arm-wrestling for the right to use an ad slogan, or celebrating the introduction of a new 737, Herb embodied the Culture of fun that he instilled at Southwest.

His engine never stopped 

“There is a difference between ‘micromanagement,’ which deprives others of initiative, creativity, and growth, and ‘micro-knowledge,’ which aids in making excellent leadership decisions.” 

Herb read voraciously—about history, chocolate, the Brooklyn Bridge, calculus, whatever. Barrett jokes that she never had to read while she worked for him because he gave her daily book reports. He loved to gather friends and stay up deep into the night, a glass of Wild Turkey in one hand and a Merit cigarette in the other, discussing the news of the day or what he had just read. His memory for names and faces translated to whatever he had read, so woe be unto the poor sucker who debated with Herb without having his or her facts straight. 

The later Herb stayed up, the more he wanted to talk, the more energized he got, the more complex the topic became. “Somewhere, somehow, he got into quantum mechanics,” Kelly says. “He was reading about quarks and string theory. I would always kid everybody: ‘When it gets to be a certain time of the night and Herb starts talking about string theory, I’m going straight for the elevator.’”

Once, Barrett says, Herb and a Pilot got in an argument at a cookout over whose car was faster. Nobody knows exactly what happened next, except that the two left the party in Dallas, and Herb called the next morning from Ennis, Texas. “Don’t ask any questions,” he said (more or less). “Just tell me how to get home.”

Once a year, Herb and his friends gathered at his ranch in West Texas to eat, drink, and tell stories. Herb loved to tell stories. “It didn’t matter if you’d heard it already,” Kelly says. “He’d say, ‘You don’t understand. I tell these stories for my enjoyment, not yours.’”

Cunningham was often Herb’s roommate on those excursions, though Herb spent almost no time in the room. Herb stayed up until dawn drinking and talking with whoever had the stamina to stay up with him. One by one, Southwest executives went to bed, but not Herb, and not the Pilots who had been invited. They thought they could hang with the leader. They learned otherwise. 

One time, Herb finally went to bed as the sun started to rise. When everyone gathered at 7:30 that morning, he was awake and refreshed and ready to attack another day. 

He was all about winning

“I love battles.” 

Southwest became Southwest because Herb never let the Company waver from its identity as a low-cost, high-volume, point-to-point airline. That approach wasn’t Herb’s idea, but he perfected it. An article in Fortune magazine said that early in his tenure, Herb approved every expenditure over $1,000 “not because I don’t trust our [P]eople, but because I know if they know I’m watching, they’ll be just that much more careful.”

The Company has made a profit every year since 1973 and has never laid off an Employee, all while revolutionizing the aviation industry. Southwest was the first airline to turn planes around in 15 minutes, and the first to offer profit sharing to Employees. It was also the first airline with a CEO who wore a grocery bag on his head in a TV commercial and boarded his planes on St. Patrick’s Day dressed like a leprechaun.

The connecting thread between personal zaniness and business savvy was that Herb was fiercely competitive about everything, even having fun. “I used to tease him [that] if he didn’t get an award plaque every four hours, he broke out in hives,” Ricks says. One time, Herb came back from an award ceremony and was the most excited that Ricks had ever seen him. Herb had received a plaque from his alma mater for his induction into the Haddon Heights High School Athletic Hall of Fame in New Jersey. “He was so pumped about that,” Ricks says, “which told me that this competitive streak he had didn’t just start with Southwest Airlines. It was something he was born with.”

Ricks chooses his words carefully. As badly as Herb wanted to win, he played fair. Herb’s strong relationships with Southwest’s unions were proof. “He had a competitive spirit that was noble,” Ricks says. “He wasn’t there to vanquish a foe just for the sake of vanquishing a foe.” 

Many of those vanquished foes became his friends. Ricks says that when he first started representing Southwest, people knew Herb everywhere they went. “People would tell me their Herb story: ‘Oh, yeah, Herb and I go way back. We did this; we did that.’ Frequently—not just once or twice, but frequently—people would say, ‘We first met as adversaries in a lawsuit.’ I would say, ‘You fought with him.’ They would say, ‘Yeah, we fought like cats and dogs. Once the case was over, he became my best friend.’”

His legacy is immeasurable 

“A company is stronger if it’s bound by love rather than by fear.” 

Herb’s legacy goes beyond just numbers, but the numbers are staggering. He helped the Company grow from having just three planes to a fleet of more than 700. He saw an airline as more than a way to get from one place to another. It was a way to change lives. By offering cheap fares, Southwest “democratized aviation,” Cunningham says. No longer were planes full of just businessmen. They were also full of families.

Schools study Herb’s management philosophy, and countless companies have tried to copy Southwest’s Culture. The airline continues to thrive in part because it hasn’t veered from his ideas of how to run a business. 

“If you forced me to choose one word, I would say his legacy is love,” Kelly says. “I think that represents so many things. You’ve got Love Field. You’ve got L-U-V [the Company’s ticker on the New York Stock Exchange]. He just had a huge heart. 

“When I first got the job at Southwest, the thing that impressed me the most—it was so unorthodox and so different—was his liberal use of the word love. He would tell all of us, all Employees, how much he loved us. Not Southwest, not the business. He said, ‘I love you.’ There’s nobody I ever worked with who talked that way. This was more than just a profit-and-loss venture for him. This was a cause. This was truly giving Americans freedom to fly, it was truly giving job security to Employees and their families. That was a powerful emotion, a passion, for him.”

Few CEOs have been as successful as Herb.

And none have ever had as much fun.