Infamous Criminals and Their Kentucky Connections

When I was 10 years old, my family and I watched the two-part TV movie Helter Skelter, an adaptation of the blockbuster true crime novel about the brutal murders committed by the Manson family in southern California in 1969.

The Charles Manson/Kentucky Connection

As you might imagine, I was terrified at what I saw, and especially so when it was revealed at the end that Charles Manson was up for parole in 1978. That was two years away, and I was CERTAIN he was going to get out and come kill us all. As we know, parole was denied.

Later, I would learn that his mother was from Ashland and that his childhood home was in Kentucky. If I'd known that at 10, well there's no telling how terrified I would have been.

Jesse James Once Robbed a Russellville KY Bank

Manson wasn't the only infamous real-life supervillain with connections to the Commonwealth; Jesse James left his mark here, too. In 1868, James and his gang rode into Russellville and robbed the Southern Bank of Kentucky. They made off with over $9,000--more than $200,000 in 2024 money--and shot and wounded the bank president. The building, which is no longer a bank, is located on the corner of South Main and West 6th Streets in Russellville.

Why Al Capone Spent Time in Louisville

There are wonderful organizations that give tours of downtown Louisville, and on those historical jaunts, the historic and beautiful Seelbach Hotel always comes up. There are many reasons, but a big one is the multiple secret passageways Al Capone would use to move from one location to another when he'd visit for the sake of gambling and bootlegging. Ghost tours of Louisville REALLY do a deep dive.

John Dillinger's Extended Stay in Kentucky

Back in the 1930s, notorious gangster John Dillinger found himself in Kentucky and hid out with his henchman in a town called Gravel Switch. They found the community so warm and hospitable that they robbed its bank.

Here's the store where Dillinger worked in the 1930s.

It shouldn't be surprising that gangsters found themselves in Kentucky more often than we might realize. We're not that far from Chicago and the path from the Windy City to, say, Atlanta or Miami is a straight shot that takes through the Bluegrass State.

However, it wouldn't hurt my feelings if people like these four men would erase Kentucky from their memory banks.

And their maps.