The Wacky Genius of Herb Kelleher

Not sure who Herb Kelleher is?

Kelleher (March 12, 1931 – January 3, 2019) was an American billionaire airline businessman and lawyer. He was the co-founder, later CEO, and chairman emeritus of Southwest Airlines until his death in 2019.

If you have ever flown Southwest or seen its ads, you know it is a different kind of airline. It does not seem to take itself too seriously, yet has had incredible success. Such traits seem to mirror those of its co-founder, Kelleher.

Here are some of the things Kelleher was known for during his years at Southwest:

  • imitating Corporal Klinger from the television show M*A*S*H by showing up at one of the company’s hangars on Halloween dressed in drag with a feathered boa.
  • appearing in print ads as Elvis Presley.
  • claiming his two greatest achievements were a talent for projectile vomiting and never having had a serious venereal disease.
  • staying at a bar with a mechanic until four in the morning to find out what is going on. And then fixing whatever is wrong.

But my favorite story is when Kelleher, age 61 at the time, settled a trademark dispute with an arm-wrestling competition.

Shortly after Southwest started using as its motto, “Just Plane Smart”, Stevens Aviation, which had been using “Plane Smart” for their motto, threatened a trademark lawsuit. The two CEOs, Kelleher of Southwest and Kurt Herwald of Stevens Aviation decided to settle the dispute in an arm-wrestling match, now known as “Malice in Dallas”. Kelleher lost the match, but was allowed to use the slogan in exchange for a $5,000 charitable donation and conceding Southwest’s legal claim to the slogan.

And even though it was way back in 1992, there is a video of the event.

(Note that this is part four of a six-part video, if you’re that intrigued, here is the link to part one)

Obviously, not your typical CEO. And his behavior may make it easier to understand the irreverent attitude of Southwest Airlines.

But I think his behavior also helps explain why Southwest has been so successful. They play hard, but they work hard to.

Perhaps it was no surprise that back in 1994 Fortune magazine had a story titled: Is Herb Kelleher America’s Best CEO?

It’s nice to know that a sense of humor and business success can go hand in hand.

*image from Forbes

27 thoughts on “The Wacky Genius of Herb Kelleher

  1. Kelleher knew there was more than one way to skin a cat (figuratively of course). For a long time Southwest was the most unionized airline in the U.S. and had the highest wages but it turned quarterly profits like clockwork. At the same time, Southwest’s domestic competitors lost money hand over fist and went through numerous bankruptcies. A major Southwest advantage was liberal work-jurisdiction rules among unions that allowed for super efficient operations. I’m glad Kelleher made the list of top-20 CEOs.

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      1. In contrast to Kelleher, some other airline CEOs just awful. I’m surprised some of them, like Frank Lorenzo who ruined Continental and Eastern, didn’t make the list of the 20 worst CEOs.

        I had never heard the story about arm wrestling for the rights to the corporate motto. Thanks for cluing me in about that, and I also hope normal operations return soon.

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      2. it is amazing how much money some of the arilines have lsot over the years.

        I’d heard about the arm-wrestling contest several years ago in a brief talk by Jim Collins, but this is the first time I actually followed up on it and read a bit about it. Kelleher did seem to enjoy the spotlight…


  2. What a character! To be honest, I’d never heard of him until your post. Imagine that—a funny billionaire. That breaks my image as I picture most rich people as serious types.

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  3. A great story to share, Jim! Quite often we feel very separated, at least socio-economically, from the executives that run the companies we work for. And then there are leaders like Kelleher who remind you we are all more the same than different. I love when someone this successful doesn’t take themselves too seriously. It is an endearing quality! Great post!

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  4. I thought I saw Kurt’s elbow come off the table before he took Herb’s arm down, but no foul was called. That was fun to watch. Kelleher’s cigarette in his mouth during the whole thing was a nice touch. And I liked one of the lines from the ring announcer, who said this was the hottest sporting event since the winter Olympics. Funny.

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