Remembering Herb Kelleher, 87, The Late Southwest Airlines Founder And Attorney, On This Memorial Day Weekend

Herb Kelleher (Photo by William Thomas Cain/Getty Images)

“My time’s more like fly time / Don’t call it getting dressed, call it in the sky time / If you ain’t a pilot, you probably couldn’t style it / Unless you was a stewardess, you won’t know what to do with this / First I took the time out, then I put the time in / Money ain’t everything, it’s more about the timing / So I got the Audemars, flawless diamonds / In other words, that’s called perfect timing / I feel like a favor, I feel like a savior / They clocking my neck, I feel like I’m Flavor.” — Fabolous

Earlier this year, Herb Kelleher, 87, passed away in Dallas, TX. Freelance writer Matt Crossman wrote a fitting tribute to the maverick, attorney, and founder in the Southwest Magazine March 2019 issue.  In honor of this airplane-industry icon, Guy Raz, Host of NPR’s How I Built This podcast, recently re-ran his November 2016 interview with Kelleher.

Throughout this interview, one can’t help but be in awe of Kelleher’s innovation, tenacity, and persistence. I’m a big fan of all of Raz’s interviews, but I especially enjoy the ones that feature law school alumni. Guy Raz has stated that his interview with Kelleher is one of his favorites and I have to agree.

At the University of Chicago, I studied Southwest’s business model in-depth for a class assignment on the Harvard Business Case Study — Rapids Rewards at Southwest Airlines. Then having gone to law school at SMU Dedman School of Law in Dallas and being a frequent flyer of Southwest Airlines, I became fascinated by and a big fan of the founding and culture of Kelleher’s progeny.

Raz’s interview of Kelleher has only added to Kelleher’s mystique. Kelleher may have stepped down from his role as Chairman of the Board in 2008, but his hearty laugh and LUVing legacy continue to reverberate to this day.  Here are some of my favorite Herb Kelleher career highlights from his feature in Southwest Magazine:

  1. Herb 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.”

  1. 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.”


  1. 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.”


  1. 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.’”


  1. “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.


  1. “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.
  1. 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…. 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…. 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.”

Many of us will be traveling this weekend and traveling specifically via Southwest Airlines. Let’s take a minute to tip our hats and tip back some glasses of Wild Turkey in honor of Herb Kelleher. For many of us, he democratized the skies. If you ever lived in Dallas, it’s likely you’ve heard a tall tale about Herb. After all, he was simply larger than life. If our lives are to be measured by our stories, then it’s safe to say that Kelleher lived one hell of a life. Hopefully, we can all claim the same when it’s time to close the cover.

RIP Herb David Kelleher, 87 (March 12, 1931 – January 3, 2019).

Renwei Chung is the Diversity Columnist at Above the Law. You can contact Renwei by email at, follow him on Twitter (@renweichung), or connect with him on LinkedIn.

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