Southwest Airlines Family and Friends Celebrate the Life and Legacy of Herb Kelleher

There were shots of Wild Turkey, musical tributes—and many, many laughs.

More than 5,000 Southwest employees, retirees, and invited guests celebrated the life and legacy of Herb Kelleher on Tuesday at the Kay Bailey Hutchinson Convention Center in downtown Dallas. Fittingly, boots and jeans far outnumbered the suits and ties in attendance. One retiree’s vintage Southwest Airlines t-shirt read: “I don’t want to grow up—that’s why I work for Herb.” And in true Kelleher fashion, there were reliably more laughs than tears during the two-hour memorial.

A pin given out at the celebration of the life of Herb Kelleher.

As you’d expect from the a dependably on-time airline, the service started promptly at 10 a.m. Longtime sidekick Colleen Barrett, president emeritus of Southwest Airlines, needed a cowbell cutoff reminder to help keep the service on time. “When you’ve worked with someone for 51 years as I did, it’s almost impossible to put these stories into any kind of sequence … [after the cowbell] no matter where I am in these stories, I’ll just stop and go to my closing remarks. Otherwise, we’d probably be here until tomorrow,” she said.

Barrett shared stories of Kelleher’s early years in business. First, as Herb’s dutiful secretary at a “stodgy” law firm in San Antonio, and then following him over to the “fun” firm Kelleher founded. She shared tales of his disdain for file folders and the time he lost his briefcase on the way to a meeting of the Conquistadores del Cielo (Conquerers of the Sky), a secret club of top airline and aerospace executives that Kelleher was initiated into in 1990. “It’s funny that a lot of Herb stories begin with booze or women, or both,” Barrett joked.

Joan Kelleher’s Wild Turkey salute

Following stories by Kelleher’s work wife, Herb’s real wife of 64 years, Joan, and the Kelleher clan—including Herb’s daughter Ruth, who is affectionately known as “Herb in a skirt”—took the stage to toast their father’s life with a swig from Wild Turkey minis. A close-up of the camera on Joan, as she sipped the whiskey and felt the slow burn of the bourbon, was a crowd pleaser.

Fort Worth native and musician Gary Morris performed “Wind Beneath My Wings” and led the audience in a rendition of “America the Beautiful.” Other speakers included an invocation by Maria Dixon Hall and a story of how Kelleher became co-commander of the U.S. Air Force—or “Co-Co” for short—by retired general Duncan McNabb.

It was Ron Ricks, vice chairman of the board at Southwest, who relayed the story of the founding of the airline on a cocktail napkin (which may or may not be myth), and the David vs. Goliath tale of stopping a temporary retraining order by Continental Airlines in order for Southwest Airlines to officially take flight on June 18, 1971. Though Ricks admitted Kelleher never told him the exact details of how he managed to assemble the Texas Supreme Court the day before Southwest flights were to begin to overturn the restraining order, he said “reliable sources” confirm seeing Herb and the justices in a dark bar off South Congress Avenue in the wee hours of the morning on June 17.

Bill Cunningham, Southwest Airline’s presiding director, regaled the audience with stories of hunting trips that doubled as executive retreats at Kelleher’s west Texas ranch, as pilots, company directors, and friends of Herb were all invited. “Sure, we carried rifles and shot guns,” he said. “But in my van, several shots were had. But they were exclusively Wild Turkey.”

Craig Hall’s ties, a gift from Kelleher

Dallas real estate developer Craig Hall recalled several handwritten “Herb notes” that he received throughout the years—including when Kelleher decided to open his own vineyard (“Thanks for the inspiration. I promise to compete fairly.”) and more recently when HALL Arts Residences high-rise project was announced (“And remember, those Russian plutocrats have lots of off-shore money to spend on lavish condos.”). But it was a gift of ties from Kelleher (which Hall told D CEO about when we visited his office earlier this year) that got the most laughter: “The attached ties screamed ‘Craig Hall’ as I walked through the men’s department at Kmart. I know you will cherish them and care for them.”

Gary Kelly, Southwest Airlines CEO

Finally, Southwest Airlines CEO Gary Kelly took the stage, reminding attendees of Kelleher’s incredible legacy. As founder of Southwest Airlines, Kelleher was responsible for building an airline that has posted “46 years of consecutive profits, no layoffs, no furloughs, and no pay cuts.” Kelly closed by comparing the revered leader to one of the UK’s most famous politicians:

“Herb had great admiration for Winston Churchill who once said of the British people: ‘They are the lion. I am the roar.’ Churchill, of course, was valiant, courageous, and inspiring. He faced unbelievable challenges and was famous for saying ‘Never, never … never give in.’ I’ve always thought that Herb was our Churchill, and like him, Herb always, always gave the credit to the people of Southwest. And also like him, Herb was tenacious and he never gave up. You’ve heard about the immense obstacles in the early days of Southwest, and thereafter. There is no doubt there would be no Southwest Airlines without Herb. There’d be no freedom to fly. And, my, what a truly awesome gift he has bequeathed to all of us.”

If you missed out, a full video of the event will be available at for the next 30 days.


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