Jack Stewart, Communications Committee, comm@swapa.org
If you’re anything like me, you probably remember what it was like as a brand-new student Pilot — big on dreams and short on cash and doing whatever it took to get one step closer to your dreams. Maybe you inherited the aviation bug, and a family member took you up on your first flight. Maybe your parents encouraged you to pursue a career in aviation but didn’t have the means to provide you with formal training. Maybe you spent time lurking around your local airport, begging for airplane rides until someone took pity on you.
Or maybe you earned money by pumping gas in San Antonio, Texas, before Southwest Airlines hired you as a Ramp agent, then Ops agent, and then you had the opportunity to take Herb Kelleher up for a spin around the patch in an experimental V-tailed Davis DA-2A at the ripe old age of 19 years old.
No? Yeah, me either. But that’s how one of our own, Kirby Chambliss, got his start. “The Pilots went nuts when they found out some Ops agent was flying around an experimental airplane with the CEO,” Kirby recalls. “They were not happy at all.” But it worked. When Kirby was 25 years old, he showed up for new hire training with 4,500 total hours (2,000 jet hours) and spent the next 25 years learning how to juggle a life on the line while building a second career as a champion aerobatic and air race Pilot.
It’s not uncommon to hear of Pilots who take advantage of the flexibility our schedule allows to chase their dreams when the parking brake is set. For many of you, putting on the uniform of a Southwest Airlines Pilot is the dream you’ve chased since you were that new student Pilot. For Kirby, it was a balancing act that involved more than 220 days a year on the road while averaging only 35 hours a year flying Company iron. And one that ultimately led to the Company granting him a 10-year leave of absence after balancing both careers for 25 years on his own.
As member and captain of the U.S. Aerobatic Team, Kirby won five national championships and 13 medals at the world championships. He was also a two-time champion of the Red Bull Air Race World Series. I think it’s safe to say that he’s a competitive person who just wants to win. According to Kirby, “I was always looking for that perfect flight … I’m all in.” But, more importantly, he remembers being that kid waving at the Pilots from the terminal or looking up into the sky and thinking, “One day …”
Most days, I still feel like that kid. It’s nice to know I’m not alone. Kirby retired from Southwest Airlines in November 2024 and lives with his wife, Kellie, in Chandler, Arizona. To learn more about how Kirby continues to inspire the next generation of Pilots and how you can contribute to the future of aviation, listen to The SWAPA Number podcast, “5,” available on swapa.org or on the SWAPA app.
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