Put simply, Kirby has a long history of audacious ideas. It was back in the early 2000s that he rose at America West to become the top lieutenant to CEO Doug Parker. In 2005, the pair orchestrated the offensive that devoured much bigger US Airways from Chapter 11. In 2007, American’s current CEO, Robert Isom, joined US Airways—America West took its target’s name—as chief operating officer and served alongside CEO Parker and president Kirby in what became known as an industry “dream team.” Kirby gained a reputation as one of the best in business at network planning and revenue management. Isom totally transformed the airline’s industry-trailing record in on-time performance baggage handling and customer service so that, within two years, US Airways ranked among the industry’s best in each category.

In December of 2013, the brain trust reprised the David-beats-Goliath playbook when US Airways snagged American from bankruptcy, and reflagged once again as the bigger name. Parker, Kirby, and Isom continued as CEO, president, and COO, respectively, mounting a comeback that by the mid-2010s, got American’s stock back near pre–Global Financial Crisis levels.

Parker made it clear that Kirby wouldn’t succeed him, and in 2016, United CEO Oscar Munoz pounced, hiring the 50-year-old as president and heir apparent. Kirby built on Munoz’s success in going upmarket, and burnished his credentials as a master of capturing high-fare business customers in the mold pioneered by Delta. “He’s the smartest person I’ve ever worked with,” says Jim Olson, who served with Kirby at US Airways and United, heading communications at both companies. “He’s like an AI supercomputer in establishing routes, but he shows it even in funny ways. At US Airways, we had this contest at quarterly all-hands meetings where they’d put out this giant jar of jelly beans, and you’d win by getting closest to actual number of beans in the jar. Kirby just eyed it and won, he was off by just a few jelly beans. He’s also extremely politically savvy, and employees love him.” (Olson just published an acclaimed memoir and crisis management guide called Tailwind: A Compass for Turning Your Setback Story Into a Comeback Legacy, featuring a foreword by Munoz, that this writer highly recommends.)

Instead of following the United and Delta push for affluent flyers, American emphasized competing on price, even removing premium rows on its aircraft. The low fares didn’t support a top product, and the airline generated low yields on seats sold. American viewed its competition as low-cost carriers such as Spirit and Frontier. Its low profitability and high debt levels made the carrier super-vulnerable to the COVID shutdown, and to survive, it piled on gigantic levels of debt that hobble its finances to this day. Its current market cap stands at just over $8 billion, one-fourth and one-fifth the respective numbers for United and Delta. Given its giant size in revenues, that American harbors such a tiny valuation underlines that investors are extremely downbeat on its prospects.

So Kirby would be pursuing a hobbled American. On this occasion, he’s confronting the leader who was part of a brainiac trio that performed the US Airways–American coup a decade ago, and now has the CEO job at his old employer. It won’t be an easy quest, that’s for sure. But given his track record, it’s not an impossible one either.