Celebrating Herb Kelleher’s Life With His Southwest Family


When Southwest founder and long-time leader Herb Kelleher died earlier this month, his loss was mourned by people all over the US and around the world. But as much as he was admired by people in and outside the industry, nobody appreciated him more than the people of Southwest Airlines. Herb’s blood relatives opted for a smaller funeral, but Southwest knew that many employees would want to find some public way to honor their leader. So it was that on Tuesday the airline hosted a “Celebration of Life” for Southwest employees to attend, and I was invited to join them.

[Disclosure: Southwest provided my flights without charge]

There aren’t a lot of airlines that can boast about having an incredibly strong culture, but Southwest isn’t a lot of airlines. Herb’s casual style, his
disarmingly welcoming demeanor, and his, as Southwest called it, “Warrior Spirit” all combined to make for a true leader that people wanted to follow through thick and thin. I don’t want to overstate this. Herb isn’t solely responsible for the culture and very well may not even been the most important piece of the puzzle — many would agree that Colleen Barrett was the true heart of the airline — but there’s no question that without Herb, there isn’t a Southwest Airlines.

That fierce loyalty meant people needed an outlet to grieve and celebrate Herb’s life, but then again, Herb wouldn’t have wanted people to grieve too much. The so-called “Celebration of Life” seemed like a good compromise. About 5,000 people (almost entirely employees) filled the arena at the Dallas convention center for a 2 hour LUV-fest that struck exactly the right tone.

The program began on an upbeat note with a drum line marching into the arena followed by the remaining original employees of Southwest Airlines. Current CEO Gary Kelly opened the event to polite applause, but it was President Emeritus Colleen Barrett who received a raucous, lengthy standing ovation. You could see the emotion on Colleen’s face, even when she swatted at the crowd to tell everyone to stop making such a fuss over her.

What followed the introductions was a remarkable mix of speakers who told stories from different parts of Herb’s life. They were all funny, and even though tissues were handed out, there wasn’t a lot of crying.

Colleen spoke about her earliest days when she began working as Herb’s assistant at a law firm. She painted a picture of a disorganized, absent-minded man who was sharp and completely lovable. Case in point – Colleen doesn’t drive, and Herb apparently left without her on multiple occasions, leaving her stranded. Yet somehow, she never ended up strangling him.

Ron Ricks, the airline’s former chief legal officer and current board vice chair, told tales from the early days at Southwest when Herb was fighting for the airline’s life. He compared Herb to Heracles, channeling his Warrior Spirit. It was a thunderous speech.

Herb’s blood relatives also made an appearance, giving a short toast chased with mini bottles of Wild Turkey that each family member pulled from their pockets. (Herb’s wife Joan took a sip, but winced at the taste which got a chuckle from the audience.)

On the surface, some of the other speakers including a retired Air Force general seemed random, but they all served an important purpose. Together, they showed just how wide Herb’s net spread, and how much people loved him.

In the image above, you can see Dallas businessman Craig Hall on the big screen. Craig was the only one on stage wearing a tie, and he explained why. Apparently many years ago, Craig attended an awards ceremony for Herb and he was the only one not wearing a tie. Herb called that out in his speech. Soon after, Herb sent Craig a tie along with a note saying he had found it at the men’s department at Kmart and it screamed Craig’s name. That was the tie that Craig wore on stage. You can read the full story in this piece Craig penned for the Dallas Morning News.

Near the end, Hudson Drake stood up in his yellow jacket, and I think my jaw dropped a little. Hudson was there representing the Conquistadores del Cielo, the secretive club that airline and aerospace executives have been a part of since the early days of aviation. Hudson, a retired aerospace executive, started to go into detail talking about the club. I didn’t know that was allowed.

Apparently the yellow jacket was for those who have been members for more than 25 years. Anyone with less than 25 years wore a green jacket. Soon after, a whole group of members in their green jackets stood up and gave Herb a rousing send-off by yelling “Viva!” which I assume has deep meaning to those inside the club. Hudson finished by reading the iconic poem “High Flight” by John Gillespie Magee, Jr. Apparently that poem is read at the induction of new members.

After 2 hours, the event was over. The only sadness I felt at the end was in knowing that I would never get to see Herb again. I only met him twice, but as anyone who has met him can attest, he left a big, lasting impression.

There aren’t a lot of people who I’ve only met twice where I’d feel compelled to fly 3 hours just to attend a celebration of life. In this case, as I left under gray skies and headed back to the airport, I could only think about how glad I was that I had made the trip.

If you’re interested in more detail about the event, the Dallas Morning News covered it in greater detail.

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9 comments on “Celebrating Herb Kelleher’s Life With His Southwest Family

  1. Herb, Bob Crandall, Fred Smith, John McCain, some 4-stars I’ve met in my time, a couple of my profs, even a few Senators, I, a nobody have met and known a little about, a couple of friends, and of course, my Dad.

    I know I didn’t agree with everything (in some cases, even a lot) they did or said, but I think the world is a better place having had (and some, still have) on this earth! Well Done!

  2. I only met HK once, was mightily impressed, and filed away in memory his cogent remarks….

    The subject?  The building of a “High Speed Rail” network linking Houston, the Metroplex, Austin, and maybe San Antonio.  Herb’s comment…”If you’ll bank the money the damn thing will cost to build and operate, then let WN have the interest, we’ll fly everyone who wants to travel within those destinations as often as they want to go, FREE!”

  3. Thanks for sharing this, Brett. Sounds like a meaningful event. Your story about meeting Herb resonated with me. I met him once during my internship at Southwest more than a decade ago. I was giddy when a group of us ran into him in the hallway on our way to lunch. He was warm, curious and genuine, as many have described him. My coworker said that if I met him again 10 years later — which I never got the chance to do — that Herb would remember our first encounter. That was all I needed to know about Herb’s character.

  4. I was in the room with you and Herb for your last photo. I have been trying to find my copies but have been unable to locate them. So long Herb. Thanks for all you did.

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