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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 (opens in a new tab) 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 (opens in a new tab).

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

The future is long-haul: We’ve been watching Alaska Airlines (opens in a new tab), 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 (opens in a new tab), stiffer network competition, and customers demanding stronger loyalty economics, Alaska introduced its own metal rather than deferring to airline partners. Southwest has clearly felt similar pressures and appears to be looking to follow the West Coast heavyweight.

• Rumors abounded that Southwest would follow in Alaska’s footsteps, but industry writer Enilria first gave the theory legs by reporting that the airline could lease ailing Norse Atlantic 787s (opens in a new tab).
• 15 months later, Reuters reports that Southwest is weighing long-haul international flights with “a fleet of dozens of 787s (opens in a new tab)”, which will likely be done through leases (opens in a new tab) 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 debated how to ‘go premium’, but without plans to introduce airport lounges (opens in a new tab), the future is unclear unless it embraces 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 use a widebody in its strategy, but it’d likely go overseas — and the reason ultimately comes down to owning more of a traveler’s journey.

The biggest misconception is key: Many, especially in travel media, misunderstand that flying 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, so decisions are guided primarily by the affluent — folks who likely choose Delta or United instead. Without a course correction, that might never change.