Southwest Airlines Founder and Chairman Emeritus Herbert D. Kelleher.
Southwest Airlines Founder and Chairman Emeritus Herbert D. Kelleher. Credit: Courtesy / Southwest Airlines

In the mid-1960s as he practiced law in San Antonio, there was no sign – aside from his gregarious personality – that Herb Kelleher was destined to become a marketing icon and visionary leader of an upstart airline.

Then he met a client named Rollin King who had the idea to start an airline that would fly three routes in Texas between Dallas, San Antonio, and Houston. The story goes that the two men drew up the plan for the airline and its routes on a cocktail napkin in a San Antonio bar. King later debunked that story, but it’s still part of the legend.

After initially attempting to talk King out of the idea, Kelleher went all-in with his friend and helped build Southwest Airlines into the guiding light it is in the aviation industry today with 45 consecutive years of profits.

The airline blossomed from a tiny Texas startup into the third largest airline in the U.S., and the one serving the most domestic passengers. Its rise to stability and prominence can be traced to a strategy of low-cost fares, customer service and never taking itself too seriously, much like Kelleher, who died Thursday at 87.

“Herb was a pioneer, a maverick, and an innovator,” the company said in a statement on its website. “His vision revolutionized commercial aviation and democratized the skies. Herb’s passion, zest for life, and insatiable investment in relationships made lasting and immeasurable impressions on all who knew him and will forever be the bedrock and esprit de corps of Southwest Airlines.”

Southwest, which is based in Dallas, did not release a cause of death.

Kelleher was born in Haddon Heights, New Jersey, and grew up on the East Coast. He attended Wesleyan University and later earned a law degree from New York University. He moved to Texas to start his own practice and soon encountered King.

Southwest took flight on June 18, 1971. A little more than a decade later, Kelleher was the president, CEO, and executive chairman who began starring in the airline’s whimsical television commercials that poked fun at him and competitors.

He wore a bag over his head in one of those commercials as he responded to the suggestion by a rival that passengers would be embarrassed to fly his airline. In later editions, he dressed up like Elvis, missed his flight, and praised himself for the airline’s success while employees rolled their eyes.

One of Southwest’s first commercials featured a leggy woman standing on a runway promising free cocktails for everyone and a schedule passengers could depend on as one of Southwest’s jets zoomed in low overhead. The commercial asked if the viewer could “Remember what it was like before Southwest Airlines?”

It was attention-grabbing, to be sure, and in stark contrast to a stuffy airline culture in those days that catered largely to business travelers and wasn’t affordable to many. The chummy personality of the co-founder manifested itself in his employees. One of the staples of Southwest flights to this day is entertaining flight attendants who are just as likely to break into song or tell jokes during safety demonstrations as they are to show passengers how to buckle their safety belts.

Airline culture changed dramatically once again in the aftermath of the Sept. 11, 2001, terrorist attacks on America. But Southwest stuck to its principles and stayed true to what had made it successful and got through lean periods without layoffs. It was something Kelleher later said was among his proudest accomplishments.

In 2017, the company reported it would share $586 million in profits with its 54,000 employees. It had done the same the previous year with $620 million.

Kelleher is survived by his wife, Joan, and three of their four children along with numerous grandchildren.

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Kyle Ringo

Kyle Ringo is a freelance journalist based in San Antonio. He has covered business, college athletics, the NBA, NFL and Major League Baseball for numerous publications and websites.