Crime

Can’t get enough of ‘The Big Conn?’ Check out more KY true crime, plus a documentary

Apple TV+ released its new docuseries “The Big Conn” Friday, which tells the bizarre tale of convicted Kentucky disability attorney Eric Conn, who orchestrated the biggest Social Security scam in history.

If you watched the show in one weekend and it left you hungry for more true crime stories set in the Bluegrass State, we’ve compiled this list of a few other productions you might enjoy.

“The Disappearance of Crystal Rogers”

The case of missing mom Crystal Rogers, a mother to five children, has drawn national attention, an investigation by the FBI and a “flood of tips” related to her sudden disappearance.

But nearly seven years later, the Bardstown native has not been found.

“The Disappearance of Crystal Rogers,” a docuseries by true crime TV channel Oxygen, focuses on the mysterious twists and turns around her disappearance over the Fourth of July weekend 2015.

The trailer for this five-episode series hones in on sleepy scenes of Bardstown, “the most beautiful small town in America.”

Light bathes this lush rural community in the heart of Kentucky, but shadows linger here, too. As one interviewee puts it: “There is something evil in that town.”

After Rogers disappears, leaving behind her vehicle with everything she has in it untouched, her father Tommy Ballard is determined to find her, only to wind up shot dead himself.

It’s only the beginning though after a police officer is ambushed and killed while driving home along a desolate road at night, and a mother and her young daughter are found brutally murdered in their Bardstown home.

Could all of these unsolved cases be connected? An investigative team aims to find out, and a box of Ballard’s notes about Rogers’ disappearance may hold the key.

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“Heist”

A departure from the darkness of our previous pick, the six-part Netflix series “Heist” aims to capture the exhilarating fantasy of making off with millions of dollars and getting away with it.

The series tells three tales, including the infamous Kentucky theft of hundreds of bottles of prized Pappy Van Winkle bourbon, known as Pappygate.

Toby Curtsinger, the man charged with the theft, looks into the camera and asks the viewer a cutting question: What would you do if you worked at a bank with a wide-open vault and no one was watching you?

“A lot of people look at it like ‘Oh I wouldn’t do that. Really?’” Curtsinger asks incredulously.

While “The Disappearance of Crystal Rogers” is more grounded, telling its story through intimate interviews with close family and friends, “Heist” plays up the fast-paced action with dramatized scenes.

As one interviewee says with a grin: “Chaos is exciting. Chaos is sexy.”

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“Hillbilly”

This documentary produced by Kentuckian Ashley York, who grew up outside of Pikeville, aims to tear down the popular stereotype of the hillbilly. The film unpacks the stereotype as a vicious caricature meant to pave the way for exploitation by powerful corporations.

The movie is offered by Hulu, and as one interviewee puts it: “It’s only a region of trash. So why not trash it?”

Through the lens of York’s camera we see not just members of the white working class, but Black folk and queer youth, all of whom proudly adopt and repurpose the label, offering their own interpretations of what it means to be a “hillbilly.”

The documentary is set in the aftermath of the political earthquake that was former President Donald Trump’s election to office in 2016, which as the film points out, the media blames on disillusioned Appalachians.

But are these people “deplorables,” as 2016 Democratic presidential candidate Hillary Clinton put it, or is there more to their story?

Do you have a question for our service journalism team? We’d like to hear from you. Fill out the form below or email ask@herald-leader.com.

Aaron Mudd
Lexington Herald-Leader
Aaron Mudd was a service journalism reporter for the Lexington Herald-Leader, Centre Daily Times and Belleville News-Democrat. He was based at the Herald-Leader in Lexington, and left the paper in February 2026. Support my work with a digital subscription
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