Improving the operation is one the top five priorities Jordan has set through 2026, but at a media day on Nov. 30, the CEO said he couldn’t put a price tag on the cost of slow modernization. At the event, executives discussed the $2 billion being spent to improve passengers’ in-flight experience — wifi systems, power outlets at seats, etc. They also talked about improving aircraft productivity and flight operations, without much detail on the costs.“We’re behind,” Jordan said at the time. “As we’ve grown, we’ve outrun our tools. If you’re in an airport, there’s a lot of paper, just turning an aircraft there’s a ton of paper. If you took our crews, we have a lot moving all over the country. If they get reassigned, someone needs to call them or chase them down in the airport and tell them.”

But at the same event, even some of Jordan’s top lieutenants rejected the idea that Southwest has been slow to adopt new technology. “That’s a leftover image from decades ago — I don’t think it’s true,” Chief Operating Officer Andrew Watterson said in an interview. “Our scheduling system is the best in the world.”