I got some bittersweet news today when I read that Gary Kelly is stepping down as CEO of Southwest Airlines. I’m happy for him that he’s going to have at least some of his personal life back (He’s staying on as Executive Chairman through 2026.), but saddened for the company’s loss.

I First Met Gary
I first met Gary back in 2000, when I was a freshly minted MBA following airline stocks. I remember sitting with him and now CFO Tammy Romo (who headed up investor relations at the time) in our offices in Minnesota and quizzing him on the competitive environment in Phoenix and Las Vegas, given America West’s presence there. I’m sure that my questions were truly ridiculous, but Gary was patient and forthcoming with the guy who had been out of school for a few months and thought he knew more about airlines than the CEO did (a common institutional investor disease).
Gotta Mention Herb
When Gary took over the reigns of the airline from Herb Kelleher, he didn’t just have big shoes to fill; he had massive shoes to fill. Like, think of the shoes that clowns wear. Or the Iron Sheik wore. He was taking over from a founder and legend who, by sheer force of wit and personality, had created a culture unlike any other.
Gary was as humble and thoughtful as Herb was extroverted and boisterous, so he had no hope of being the next Herb Kelleher. Instead, he did what he had always done as CFO. He trusted the system: Treat the employees well and keep the product simple. There’s a reason that Southwest lets customers carry on two bags for free. But most importantly, in a culture-driven organization, he didn’t try to make the airline about him. He stayed as humble as ever on his quarterly conference call while always giving credit to the employees. The last time I was in their headquarters, they still had pictures of employees’ pets in the lobby.
In an industry notorious for cyclicality and bankruptcy (and not always in that order), Southwest has managed to grow its profitability without conducting layoffs, building itself up from a few planes to the largest domestic carrier. That’s not only unheard of in the airline industry; it’s unheard of in any industry. Many airlines have tried to imitate the Southwest model, but that’s next to impossible. It’s not as much about the model as it is the people.
Final Thought – Gary Kelly Southwest Airlines CEO Retires
One final thought: Today is my 19th wedding anniversary. Why is that relevant? Mostly because I met my wife at a combined Southwest/American Airlines analyst day(s) in 2000 (Actually, I kind of stalked her into an elevator, but that’s a story for another time.). So that’s just another “thank you” that I owe Gary (My wife might not be so grateful, but she’s stuck with me now.) as he flies off into the sunset. It’s rare that I feel enough of a personal connection to associate a personal event with a business one, but that’s always been the case for me with Southwest.
Bob Jordan is also a long-time Southwest team member and will make an outstanding CEO but, just as it’s impossible to replace Herb, it will be similarly impossible to replace Gary. Good luck out there Bob.

