History Factory president Jason Dressel recently sat down with Richard West, corporate historian at Southwest Airlines, to discuss the company’s upcoming 50th anniversary and the brand’s fascinating origins. Check out the latest “History Factory Plugged In” podcast episode for the full interview.

Jason Dressel : Richard, welcome to “History Factory Plugged In.” Thanks so much for joining us, and happy anniversary to Southwest. Can you share a little bit about the origin of Southwest? What was the initial vision for the airline, and what challenges did it encounter getting off the ground, so to speak?

Richard West: Well, June 18, 1971, is certainly a huge date in our history. That morning was our very first commercial flight. We left Love Field around 7 a.m. to go down to San Antonio, and it’s a date that we’ve celebrated every year since. So, we’ll hit that big five-oh mark this month.

But I really like to say that’s not where the story begins. I would probably say that the unofficial birthday is actually March 15, 1967. And that’s the day that Herb Kelleher filed with the state of Texas to incorporate a new company, which at the time was known as Air Southwest.

That story began one fall evening at a cocktail lounge in San Antonio, the St. Anthony Club specifically, which was right across the street from Herb Kelleher’s law firm. That day, he had been meeting with one of his clients by the name of Rollin King, who was another businessman who had a smaller airline. It flew some turboprop airplanes to some smaller cities around Texas, but it never really took off. Pardon the pun. Rollin approached Herb to actually dissolve that company. But in the course of the conversation, he said, “You know what? My banker has actually been out in California, and he saw how they have airlines that fly pretty much just within the borders of the state of California. He thought that might be something worth considering in Texas, and I think it’s worth a shot.” So they agreed to discuss it after the day’s official business was done, over drinks. That particular afternoon or evening is when the legend of the cocktail napkin began, where they sat down at the St. Anthony and sketched out that famous Texas triangle connecting the cities of Dallas, Houston and San Antonio. And it became our first business plan.

So, in the late 1960s, we had a thing called the Texas Aeronautics Commission, and that was where Southwest applied to actually get that very first operating certificate. On February 20, 1968, the Texas Aeronautics Commission voted unanimously to grant that certification. But the very next day, the legacy airlines, including Braniff and Trans Texas and Continental, went to court to get a temporary restraining order to prevent the Texas Aeronautics Commission from actually providing that certificate to Southwest so that we could continue pursuing those very first operations.

Herb Kelleher spent the better part of the next 2½ years from courtroom to courtroom, not just in the state of Texas, but at the federal level in New Orleans and finally, in December of 1970, it took him all the way to the United States Supreme Court.

But it was something that over the course of that 2½ years had pretty much bankrupted what was an airline with no employees and no airplanes, to the point that the board of directors had even said, “You know what, folks? This doesn’t look like it’s going to work out.” And everyone except for Herb Kelleher had given up, to the point where Herb said, “You know what? I want to take this one more round, and I’ll actually pay the expenses out of my own pocket.” And that’s what he did to actually get to the doors of the United States Supreme Court. Thank goodness he did, because he was right.

I would say my favorite way that I’ve ever heard it described is how Southwest democratized the skies. At the time of our first flight, I think it was something like less than 1 in 5 people in the United States had ever been on an airplane. Southwest really changed that. There were so many more opportunities for folks to take a trip where they would have otherwise driven their car. The 250 miles or so between cities like Dallas and Houston — to be able to make that into an affordable day trip meant really providing that access to travel for both business and for leisure to a good segment of the population that would have otherwise never been on an airplane.

JD: And I have to say, one of the craziest and certainly one of my favorite stories about Southwest has to be what became known as the “Malice in Dallas.” What was that all about?

RW: Gosh, it’s probably one of the craziest stories you’ll ever hear. In late 1991, Southwest began using the slogan “Just Plane Smart.” There was another company called Stevens Aviation that actually had been using “Plane Smart” in some of their promotions. Now, Stevens wasn’t an airline, but they did see that there was a company over in Texas that was using a very similar slogan. Their president at the time called Southwest Airlines and said, “Hey, you’re using my slogan. I think we should discuss it.” And we all know where that usually goes. But Herb Kelleher saw an opportunity to make something positive out of this. In March of 1992, the two leaders agreed to have an arm-wrestling competition to settle the dispute. The two of them actually went to the Dallas Sportatorium and went into the squared circle to settle the disagreement. At the end, Stevens Aviation actually did end up winning the competition, but the two agreed to share the term. Instead of spending hundreds of thousands of dollars on litigation, they both made a donation to each other’s favorite charity.

JD: Well, Richard, it’s an amazing company, and it’s an iconic brand. And it’s been a pleasure to talk to you about it and to work with you and your colleagues at Southwest on the 50th anniversary. What the company doing for the 50th?

RW: We’re working on a website, Southwest50.com, where you can see quite a bit more about our history and what we’re doing to celebrate. We’re getting ready for that big 50th celebration, where we’ll have a small gathering that’ll be down in Houston for a group of employees that won an opportunity to attend in a raffle. And it will be streamed for all 60,000 of our employees to take part in virtually as well. But it doesn’t end there.

There are actually several books in the works. History Factory has been kind enough to help us find some of those wonderful stories in our past and not just tell them in a black-and-white format, but in a way that we can really get a good 360 on what some of those great tales are about Southwest and how we can share them both with our employees and the fans of our brand outside of our walls as well.

JD: Awesome, Richard. Happy 50th, and we look forward to seeing you soon.

For the full episode and to learn more about Southwest Airlines’ 50th anniversary, click here or listen in the player below.

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