Retiring Southwest CEO Gary Kelly on What He Sees as His Legacy

It's rare in any industry for a CEO to stay on top of his or her company for nearly two decades, let alone in the rapidly changing airline sector.

To say that Gary Kelly has seen it all would be understatement. Kelly will retire in February after 35 years at Southwest Airlines, or most of the company's 50-year history, a stretch of time that has seen the airline transform itself from a discount carrier beloved by price-conscious vacationers to one of the country's largest airlines, with a thriving and lucrative corporate travel business. 

After 17 years at the helm of Southwest, Kelly will pass the torch to Robert Jordan, a company veteran who now is executive vice president for corporate services. Kelly, who trained as an accountant, came to the company in 1986 as controller, joining from Arthur Young & Co.

On the heels of his big announcement last week, Kelly, 66, spoke on Monday with Skift's Airline Weekly about his legacy, the pandemic recovery, and where Southwest is headed.

"In 1986, we weren't that different than we were in 1971," Kelly said. The airline then still was focused on short routes, mainly from Texas and neighboring states. It was hamstrung by the Wright Amendment, which limited the number of states it could reach from its base in Dallas Love Field. Southwest then was still the disruptor whose right to fly founder Herb Kelleher defended before the U.S. Supreme Court. 

But in the decades since, Southwest has reinvented itself, with much of that occurring since Kelly took the top job in 2004. When he took over, the airline industry was reeling from the post-9/11 travel slump and shortly would be confronted with the Great Rec