You'll always be my sweethearts

Know what this newsletter needs? More installments about frequent flyer programs.

After yesterday’s story about Thomas Plaskett and the invention of the modern frequent-flyer program, a couple of readers wrote back with the same reaction: Wait, what’s this thing you mentioned called the Southwest Sweethearts Club?

Uh-oh. Like a lot of people (maybe mostly men? not sure), if there’s one thing that gets me going—it’s when someone asks me a pointed factual question about an obscure thing that I happen to know something about.

So, let’s dive in with the story of a strange little corner of business history that’s equal parts clever, dated, and revealing.

The short version is that in 1972, just a year after it started flying, Southwest Airlines launched what was really the frist airline loyalty program, beating out Plaskett by a decade.

But it wasn’t for the passengers. It was for their secretaries.

The premise of the Southwest Sweetharts Club was simple: secretaries who booked their bosses’ flights on Southwest earned coupons. Rack up enough, and they could win free trips or enter raffles for vacations. They also got a monthly newsletter full of updates, recipes, social notes, and beauty tips.

If that sounds wildly sexist by modern standards, that’s because it was! It also reflected the business reality of the time: most business travelers were men; most off their assistants were women.

The reason we even know about the Sweethearts Club at all is because a Southwest intern named Lauren Webb dug up the information decades later and wrote about it on the company’s blog back in 2013.

That post has since vanished from the live internet, but thanks to the Internet Archive, it’s still preserved here.

There was also a related Valentine’s-themed promotion for business travelers offering a “‘Sweetheart’ fare card” good for $5 off if they brought their “best girl” along on a flight.

Just pointing that while one’s “best girl” might be a wife or girlfriend, it sure sounds like the idea was for high-powered business executives to bring their secretaries along. ($5 off!)

Ah, the 1970s.

So how did Southwest manage to run a rewards program like this a full decade before American Airlines created AAdvantage, the modern frequent-flyer program Plaskett is credited with building?

The answer is regulation.

Before the early 1980s, the airline industry was tightly controlled by the federal government. Routes and prices were regulated, and there wasn’t much room for competition or experimentation. American and the other big national carriers couldn’t easily roll out big marketing innovations tied to pricing or loyalty.

Southwest, however, flew only within Texas in its early years. That meant it operated outside the federal regulatory system. In many ways, the whole point of Southwest’s original existence was to exploit this federalism loophole.

So while American Airlines and the other big national and international airlines were constrained, Southwest could try a cheeky loyalty program aimed at the people booking tickets instead of the people flying.

A decade later, once deregulation hit, Plaskett and American Airlines built the computer-driven AAdvantage program, and that became the model everyone copied. That’s the system we still live with now: points, miles, status, upgrades, and a huge hidden business where airlines sell billions of dollars’ worth of miles to banks and credit-card companies.

But the Sweethearts Club came first.

Which brings me to the other reason I’ve been thinking about frequent-flyer programs this week.

Honestly, it’s because all writing is autobiographical.

Earlier this month I mentioned taking my family on a spring break trip to Aruba, and a reader wrote to say something along the lines of: Must be nice to be able to afford a trip like that!

And it is nice! It’s a fair point, I suppose. Travel is expensive.

But, I have the zeal of a convert when it comes to collecting miles and points and using them for trips.

I’m not one of those people who is perfectly optimized, putting every purchase on the exact right card to maximize rewards. But I’ve done enough over the years to make it possible to cover a lot of travel that we probably wouldn’t pay cash for otherwise.

So in a very real way, those vacations trace back to Thomas Plaskett and the birth of AAdvantage.

And in a much stranger, earlier way, they also trace back to a tiny upstart airline in Texas that decided to reward secretaries for booking flights.

So thanks to Plaskett. Thanks to Lauren Webb, the intern who rediscovered the story.

And thanks to the readers who email me and spark ideas for what to write next.

You’ll always be my sweethearts!

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Other things:

• The Trump administration tried but failed to indict six Democrats in Congress this week: two U.S. senators and four members of the House, after they posted a social media video reminding members of the military and intelligence community that they are obligated to refuse illegal orders. Trump had previously accused all six of “SEDITIOUS BEHAVIOR, punishable by DEATH!” It is extremely unusual for a grand jury to refuse to issue an indictment in any case when a prosecutor seeks one, since the standard of proof is very low, and defendants aren’t even told about the proceedings, let alone allowed to offer a defense. (CNBC)

• A man who took part in the 6 January 2021 attack on the US Capitol and was later pardoned by Donald Trump was found guilty on Tuesday of multiple child sexual abuse charges, including molesting a child under 12 and another under 16. “He is exposed to the possibility of life in prison,” said Walter Forgie, chief assistant state attorney for Florida’s fifth judicial circuit. (The Guardian)

• U.S. Commerce Secretary Howard Lutnick acknowledged under oath that he went to Epstein’s island in 2012, four years after Epstein’s first criminal conviction, said the visit was brief and that he was there with “my children, with my nannies and my wife all together.” Lutnick had claimed in October that he hadn’t had contact with Epstein since 2005, but “multiple emails from the Epstein files indicate that Lutnick did have contact [Epstein] as recently as 2018.” (People)

• In other Lutnik news: Why did President Trump threaten Canada this week and promise to block the opening of a new bridge connecting Detroit with Windsor, Ontario? It might be because Matthew Moroun, a trucking magnate whose family has operated the competing Ambassador Bridge met with Lutnick on Monday, and Lutnick then spoke with President Trump by phone shortly afterward. (NYT)

• Gallup will no longer track presidential approval ratings after more than eight decades doing so, the public opinion polling agency confirmed to The Hill on Wednesday. In what I guess was now apparently the last-ever Gallup poll on the matter, President Trump had a 37% approval rating, down from 47% a year ago. (The Hill)

• A former Meta safety researcher told a New Mexico jury that his 14-year-old daughter was bombarded with sexually explicit pictures and propositions within just days of creating her first Instagram account. Arturo Béjar, who led a safety-focused team at Mark Zuckerberg’s company from 2009 to 2015, said he returned to Meta as a consultant in 2019 after becoming alarmed at the sick messages his daughter had received. (New York Post)

• James Van Der Beek has died. The actor, best known for his roles in Dawson’s Creek and Varsity Blues, died after a journey with stage 3 colorectal cancer. His wife, Kimberly Van Der Beek, announced the news on Instagram. Van Der Beek, who shared six kids with Kimberly, first shared his cancer diagnosis in November 2024, saying he was focusing on his health and family. (People)

Thanks for reading. Photo by Sawada Kedavra on Unsplash. I wrote about some of this before on Inc.com. See you in the comments.