How a fake tech CEO duped an Alabama town

A real-life "Marge vs. the Monorail"?

One of my favorite episodes of The Simpsons is “Marge vs. the Monorail.”

It was written by Conan O’Brien in 1993. Many consider it one of the best episodes in the show’s history. In it, Springfield has come into a $3 million windfall after Mr. Burns gets fined for illegally dumping toxic waste. During a town hall meeting, a smooth-talking conman named Lyle Lanley, voiced by Phil Hartman (RIP), convinces the townspeople to invest the money in a faulty monorail system, after charming them with a catchy song and dance number, “The Monorail Song.” (Apu: "Is there a chance the track could bend?" / Lyle: "Not on your life, my Hindu friend!" )

Construction begins, but Marge grows suspicious after learning that Lyle scammed a neighboring town. With Homer in the conductor seat, the monorail almost immediately malfunctions. Lanley escapes by plane, but crash lands in a village he’d previously scammed, and is set upon by angry villagers. In the end, Springfield is stuck with a useless monorail system, but the town simply shrugs it off.

Until recently, I had no idea that this iconic episode was in fact a parody of an even more iconic musical, The Music Man. Set in 1912, The Music Man follows a charming con man as he dupes the town of River City, Iowa, into investing in a boys marching band, despite having no musical knowledge and no interest in teaching boys how to play instruments. He’s ultimately exposed as a fraud by the mayor, but instead of skipping town like Lyle Lanley, he sticks around, ultimately redeeming himself in the eyes of the community.

It was The Simpsons’ parody version of The Music Man that came to mind when I first read about Kyle Sandler’s attempt to transform Opelika, Alabama into the Silicon Valley of the South, which we chronicled in a recent episode of Gone South.

Here’s Kyle, in the midst of the scam, at SXSW.

The story was published in the Associated Press in February 2019. It remains one of the best AP stories I’ve ever read. Rarely in my career have I read a news story that feels like a fully fleshed out feature film. I remember finishing it and shouting “Holy shit!” Not only did it feel like a real-life version of “Marge vs. The Monorail” (aka The Music Man), but it featured John McAfee, the former fugitive, Cyber Party presidential candidate, and paranoid creator of the McAfee Antivirus Software, at the center of it.

In fact, here’s McAfee on Twitter, talking about getting scammed by Kyle a few days after Kyle’s arrest. The tweet reads: “My comments on the Washington Post story today about Kyle Sandler - the slickest scam artist I ever met.”

I helped develop the story as an episode of the HBO documentary series Generation Hustle, titled “The Alabama Exit.” I recorded a number of phone interviews with Kyle Sandler in prison. It was probably my favorite episode of the series, directed by the super-talented Martha Shane (Miss Americana, etc). In HBO’s transition to Max, they tragically pulled the series from their catalog. I’m told it’s only available to stream overseas. So I was very happy to get a chance to talk to the story’s two main characters, Emily Baas and Kyle Sandler, for Gone South.

As we mention in the show, Emily is now overseeing a network of thriving co-working spaces in Opelika. Kyle co-runs a website called Federal Prison Tips, which, according to its website, offers help and advice to people facing stints in federal prison. He also runs the company’s lively TikTok account.

I used to think that people who fell for scams were gullible and naive. Then I got scammed myself, and read Maria Konnikova’s The Confidence Game, and now I sympathize deeply with all scam victims in the belief that it can happen to anyone (even though I know most people think that’s only what gullible and naive scam victims say). Which is to say I sympathized deeply with the townspeople of Opelika, Alabama, who believed that con artist Kyle Sandler really did intend to turn their little railroad town into the next Menlo Park. The town had big dreams, and Kyle wanted to make them a reality. And in Kyle’s telling, he would have, if he hadn’t gotten so carried away leasing those Hummers and Maseratis, and taking his various mistresses to New York City to see Hamilton, and working as John McAfee’s presidential campaign manager, and going to Vegas to (slow fade to silence).

To the scam victim, the scam often seems embarrassingly obvious in retrospect. To those not taken in by the scam, it seems obvious from the start. As you look at the following photos from Kyle Sandler’s Facebook page, you may be tempted to think, “They thought this guy was a millionaire tech exec?” But I ask that you reserve judgment. After all, you were (most likely) not in Opelika, Alabama when Kyle pulled into town in 2014. You had not invested your hopes and dreams in the transformative power of a fiber optic Internet network, only to see a handful of families sign up for it due to its prohibitive cost ($500/month!). Most importantly, you were never in a room with Kyle, where his Silicon Valley patter and infectious energy and world-changing ambitions had an opportunity to work its magic on you in person. If you had been, it’s quite possible that Kyle Sandler would have taken you too for a ride.

Thanks for reading.

Jed