Talk about a headline that left me disappointed.
When I saw that Men’s Journal headline teasing Southwest Airlines CEO Bob Jordan’s two-word response to scrapping the airline’s historic no-nickel-and-diming ethos, I had a glimmer of hope. Maybe Jordan had channeled his inner Jamie Dimon and let fly with the infamous potty mouth of JPMorganChase’s CEO.
Perhaps it’s a generational thing, but in my day, when someone tried to justify a controversial move with just two words, the first one started with an “F” and the second with a “Y.”
Jordan, to his credit — or his PR guardian’s — gave a quote that’s printable even in his church bulletins. His unapologetic two-word defense? “Low risk.”
Southwest, once beloved for its low fares, open seating, and refusal to gouge passengers with hidden fees, is now hurtling down the same path as Spirit Airlines — but with the 10-gallon flair you’d expect from a Dallas-based company.
The new baggage fees are just the beginning. That first checked bag? $35.
Ka-ching.
The second? $45.
Ka-ching.
And now, for the traveler who’d like to skip the terminal schlep and check a bag curbside? That’ll be another $3 — per bag.
Ka-ching.
Gary Leff, the industry’s Casablanca-quoting blogging bard, flagged the curbside fee this weekend, calling it “petty.” He also noted the new charge followed Southwest’s decision to fire all its Skycaps and outsource the job to Bags, Inc. — the same vendor American Airlines uses.
“Once again, Southwest is copying their less successful competitors in an unrelenting march toward enshitification,” Leff wrote. (Yes, he misspelled the word — which I mistakenly thought he coined. Credit actually goes Canadian writer and activist Cory Doctorow, who popularized “enshittification” in a 2022 essay on the slow rot of Amazon’s website.)
Leff reports that the airline once known for “Transfarency” — the radical idea that your ticket price should reflect the full cost of your travel — is now imposing a laundry list of passenger penalties: checked bag fees, basic economy restrictions, seat selection charges, and even expiration dates on travel credits.
And Jordan’s just getting started looking for ways to goose his revenues.
This week, Southwest disclosed it’s in “discussions” to launch an interline agreement with Taiwan-based China Airlines. As The Points Guy website reported, the arrangement would let customers book China Airlines-operated flights to Taipei directly through Southwest’s app and website. If the deal closes, Rapid Rewards members might eventually be able to redeem points on transpacific flights.
That announcement comes just months after Southwest’s first international tie-up — with Icelandair — signaling the carrier’s ambition to be more than just a domestic discounter.
Let’s not be too hard on Bob Jordan. As airline CEOs go, he strikes me as an upstanding guy — bordering on sainthood.
Jordan works for peanuts — quite fitting for someone in the airline business. He took home a measly $10.6 million in 2024 compensation, making him a piker compared to United’s Scott Kirby ($33.9 million) and Delta’s Ed Bastian ($27.1 million). In the current CEO sweepstakes, that’s practically minimum wage.
Unlike so many of CEOs these days, Jordan isn’t a hotshot hired gun just passing through on his way to a better stock option package. He’s a Southwest lifer, having joined the airline in 1988 as a programmer in the IT department. Over the years, he racked up 15 executive roles — in finance, planning, procurement, fuel, facilities, technology, and corporate strategy — eventually serving as chief commercial officer before being tapped as CEO.
Jordan and his wife, Kelly, are active in charitable causes that reflect their values. They support Cross Timbers Community Church — a prominent evangelical congregation near Southwest’s headquarters — as well as Compassion International, a Christian nonprofit focused on aiding children in poverty, and SOS International, another child-focused humanitarian group.
Notably, Jordan came of professional age at Southwest when the airline was still run by Herb Kelleher — one of the last corporate leaders in America who understood that capitalism could benefit all Americans.
Kelleher co-founded Southwest in 1967, ran it as CEO from 1981 to 2001, and remained chairman until 2008. He was more than a CEO; he was a living legend.
Kelleher, who died six years ago, had compassion, charisma, and a philosophy that treating employees well would translate into passengers being treated well. He considered workers colleagues, not disposable labor units. He was famous for donning ridiculous costumes at company events and for handwriting thousands of personal notes to employees over his tenure.
Under Kelleher, Southwest was consistently profitable — even as rival carriers were tanking or pleading for federal bailouts. He built a cult of personality not out of narcissism, but out of loyalty and shared purpose.
Jordan was likely shaped in Kelleher’s mold. The tragedy is that he now seems willing to burn the house that Herb built — just to keep his job and possibly ensure Southwest’s independence.
Jordan these days is accountable to another living legend — one who, in most circles, assuredly won’t be fondly remembered or admired like Herb Kelleher.
It’s a Florida-based hedge fund called Elliott Investment Management (EIM), a firm so ruthless that the mere mention of its name is enough to make many CEOs — and even finance ministers — soil their undergarments. Elliott’s “value extraction” playbook has no moral boundaries, as Argentina learned the hard way.
In 2012, after a decade-long legal fight over defaulted sovereign bonds, Elliott convinced a court in Ghana to detain the ARA Libertad, a three-masted Argentine naval training frigate docked in the country. The ship — a floating symbol of national pride — was effectively taken hostage in a high-stakes debt standoff. It took international legal wrangling, United Nations involvement, and a diplomatic uproar to finally secure its release.
Elliott’s take-no-prisoners model is simple: target companies with sagging stock prices, buy a stake big enough to rattle the boardroom, and then demand ruthless cost-cutting, executive firings, new revenue streams, breakups, or asset sales — whatever it takes to juice short-term returns. Then cash out and move on to the next target.
Long-term vision, employee loyalty, and customer goodwill? That’s for HR and brand consultants. Elliott founder and co-CEO Paul Singer didn’t build a $73 billion empire — or his own $6.2 billion net worth — on compassion. He built it on leverage and pressure.
Last year, Elliott acquired an 11% stake in Southwest Airlines and promptly released a scathing assessment of the company’s management. The firm blasted “poor execution” and “leadership’s stubborn unwillingness” to adapt its business model, which it claimed led to “deeply disappointing results for shareholders, employees, and customers alike.”
Elliott demanded the ouster of CEO Jordan and chairman Gary Kelly, accusing the latter of overseeing “a period of stunning underperformance.” Kelly, who served as CEO for 17 years before handing the reins to Jordan in 2022, was removed in a board shake-up orchestrated by Elliott last November. Elliott secured five board seats — the most it has ever gained through a U.S. corporate settlement, according to Reuters. One of those directors: David Cush, the former Virgin America CEO, whom I personally hold responsible for destroying one of the best airlines America ever had — a carrier with a cult following that included yours truly.
Jordan survived the coup, but he knows exactly what he must do to keep his job.
R.I.P., Herb Kelleher. Your legacy is being dismantled in real time. America is fast becoming a country of haves and have-nots — and flying Southwest is about to become yet another immersive experience in all that’s wrong with corporate America.