The Little Chicago Era part 1: Bootleggers in the Bluegrass

BOWLING GREEN, Ky. (WBKO) -Beneath the streets of downtown Bowling Green lies a hidden piece of history that helped earn the city a notorious nickname decades ago. Whiskey Run, an underground waterway that winds through the city’s sewer system, served as more than just drainage during Prohibition; it was a lifeline for bootleggers and criminals who helped to give Bowling Green the moniker “Little Chicago.”

The story begins with Bowling Green’s unique infrastructure. The city’s sewer system developed organically over decades, initially using natural cave systems before evolving into a more organized network.

“Bowling Green’s sewer system is very unique in that it’s kind of been pieced together over the decades, kind of as-needed,” said Bowling Green downtown development coordinator, Telia Butler. “It started out just using the cave system as a sewer release, and then as Bowling Green continued to grow, we figured out ‘Oh hey, we need to be organizing our water better and utilizing our resources better. We need to be creating actual sewers instead of just using the cave system.’”

During Prohibition, when alcohol was banned nationwide, bootleggers discovered the underground system’s potential. The network running from the Barren River through downtown Bowling Green became a secret highway for transporting illegal liquor — and disposing of evidence when law enforcement closed in.

The criminal activity wasn’t limited to bootlegging. The underground passages facilitated various forms of organized crime that plagued the city during this era.

“There’s been a lot of other unusual circumstances around the Whiskey Run area, not just related to the illegal bootlegging, but also to just some organized crime and thefts in Bowling Green’s history in general,” Butler said.

The criminal undercurrent became so pervasive that residents began calling their city “Little Chicago,” referencing the crime-ridden reputation of the Illinois metropolis during the same period.

One of the most intriguing chapters in Whiskey Run’s history occurred in 1957, when heavy rainfall produced an unexpected discovery. Large quantities of cash began flowing through the underground system and emerging from storm drains throughout the city.

The FBI connected the mysterious money to an unsolved 1949 bank robbery in Tennessee. Investigators believe the stolen cash had been hidden in the cave system for years before floodwaters carried it through Whiskey Run and into the open.

“The FBI believes that that money came from that 1949 bank robbery in Tennessee because the money was never found for all those years that they were looking for it in Tennessee,” Butler said. “And it’s believed that the gang that stole it traveled up this direction, and we think that the money ended up in a cave somewhere and then ended up flowing out of a flood water.”

Today, Whiskey Run continues to flow beneath Bowling Green’s streets, serving as a buried reminder of an era when the city’s underground carried more than just rainwater.