"Herb had the restraint not to impose his will on what I was trying to do six months earlier, and that was remarkable," Kelly said. "That was just one [disagreement]. There are millions of times where we're in lock step."
Kelly is known as a long-term strategist and a bit of a wildcatter. He's largely responsible for implementing financial maneuvers that hedge against the biggest bugaboo of the airline industry: energy prices.
Detractors disparage Kelly as a numbers guy who added a dose of tough love to the love airline.
"He is," aviation consultant Boyd said. "That's exactly why Southwest isn't broke."
His company, Boyd Group International, consults with Southwest's pilots union, and that has given him a "unique respect" for Kelly.
Boyd describes the union's naturally confrontational relationship as one of "the loyal opposition as opposed to death to the infidel. It's adversarial to get to a goal, not adversarial to hurt. That's tough to maintain, and Gary's done it."
Thom McDaniel, president of Transport Workers Union Local 556, which represents Southwest's flight attendants, said his members appreciated Kelly's attention to the bottom line while trying to preserve the company culture.
"Gary has always said job security is incredibly important to him. As a union leader, it is to me," McDaniel said. "Without those things that are the hallmarks of Southwest Airlines, we would be in a very bad place."
Conversely, the analysts say Kelly's too soft. Carl Kuwitzky, president of Southwest Airlines Pilots' Assn., has heard them criticize Kelly for letting those bags fly free.
"Although our business traffic is weak, our overall traffic clearly shows that that was a good move," Kuwitzky said. "The fact that we made money last year when virtually nobody else did is phenomenal."
Hall writes for the Dallas Morning News / McClatchy.