Southwest Has Gotten Everything Wrong With Customers Since Hostile Investor Takeover — But It’s Reading the Tealeaves on its Future

A vulture activist investor descended on Southwest in 2024. By the time it was through with this “company with heart,” it was devoid of everything that made it unique. 

Business has boomed, investors have taken their cash to the bank, and its customers have been left with a completely different, inferior experience — we called it Southworst back in June.

But while Southwest has lost the free bags, open seating, and never-expiring credits and points, they might be about to get something genuinely new from the carrier. 

The future is long-haul: We’ve been watching Alaska Airlines, which bought Hawaiian Airlines in 2024 embrace international ambitions after decades of operating a 737-heavy fleet as a regional player. Its reason was simple: ‘compete or perish.’ Amid rapid premiumization, stiffer network competition, and customers demanding stronger loyalty economics, Alaska introduced its own metal rather than deferring to airline partners. Similar pressures have obviously been felt by Southwest, which evidently looks to take after the west coast heavyweight.

• There were rumors abound that Southwest would follow in Alaska’s footsteps, but industry writer named Enilria first gave the theory legs by reporting that the airline could lease ailing Norse Atlantic’s 787s.
• 15 months later, Reuters reports that Southwest is weighing long-haul international flights with “a fleet of dozens of 787s”, which will likely be done through leases or second-hand purchases since the Boeing 787 is sold through decade-end.

The long arm of airlinedom leans towards owning the journey

Southwest has been wrong about a lot of things, but it likely isn’t wrong about this one thing — it likely can’t contend with other US carriers without a strategy to own more of a customer’s journey. Southwest has long been an airline for leisure travelers, but it’s not seen as a premium player. 

• Old Southwest isn’t coming back: The airline has quarreled with how to ‘go premium’, but absent plans to introduce airport lounges, it’s unclear what the future holds absent embracing the models already popular with other major airlines.
• Partnerships don’t let you own the journey: Alaska had oneworld and various airline partners, but as Southwest has begun building that infrastructure from scratch, it has likely learned the pitfalls that forced Alaska to fly its own metal.
• Affluents want to go the distance with you: It remains to be seen how Southwest would utilize a widebody in its strategy, but it’d likely be going overseas — and the reason why ultimately comes down to owning more of a traveler’s journey.

The biggest misconception is key: Many, especially those in the travel media, misunderstand that flying itself has always been a luxury activity. Yes, it has become more accessible, but roughly half of Americans don’t fly at all in any given year. It is expensive, and that means that decisions are guided primarily by affluents — folks who likely focus on Delta or United instead. Without a course correction, that might never change.