I just don't like to believe that something as sophisticated as a $20b company can be boiled down by over-simplified observations you and I make from the co

I just don't like to believe that something as sophisticated as a $20b company can be boiled down by over-simplified observations you and I make from the comfort of our desks. It really is pretty simple. Herb ran a cult of personality, but that personality was that of a CEO of a scrappy little low cost regional carrier back in the 70s. That sort of loyalty dies hard. It's worth noting that Gary Kelly (chairman, ex-CEO) was not an outsider. His fuel hedges cut Southwest a ton of operational slack. That slack meant there was no incentive to spend money on operational improvements. Bob Jordan's not an outsider either, he worked his way up the ranks from a code monkey to CEO. That means they both were fully invested in the cult of Herb, and both failed up. The excessively hands on recovery plan would've been manageable at a much smaller airline. From Southwest's little PR piece on Bob: During his more than three decades at Southwest, the airline grew from a regional presence with around 7,000 People and 90 airplanes to a beloved national brand with more 54,000 People and a Customer base that topped 130 million Passengers in 2019. Bob has been responsible for the delivery of many key Company initiatives, including executive oversight for development of the Southwest.com e-commerce platform, the revamp of the Rapid Rewards® loyalty program in 2011, the $3.2B acquisition and integration of AirTran Airways, the comprehensive "Heart" brand refresh in 2014, significant domestic and international network expansion, and the 2017 switch to a new reservations system. Tech struggles are nothing new for Southwest, rumor has it one of the big challenges they had with the expansion into Mexico was figuring out how to accept payments in non-USD.