730 - The O'Connor Layover - live

The Dollop dives into the bizarre and fascinating history of St. Paul, Minnesota, during the early 20th century, focusing on the O'Connor Layover Agreement—a decades-long system where the city effectively became a sanctuary for criminals. Hosts Dave Anthony and Gareth Reynolds explore how Police Chief John J. O'Connor, known as 'the big fellow O'Connor,' created a unique arrangement: criminals could legally stay in St. Paul as long as they refrained from committing crimes within the city limits. This 'organized intelligence' approach led to a dramatic drop in crime, turning St. Paul into a crime-free haven that attracted gangsters, bootleggers, and even celebrities like Duke Ellington and Cab Calloway. The city became the 'Vegas of the Midwest,' with a thriving underworld led by figures like Dapper Dan Hogan, a charismatic fence and liaison who kept the peace through diplomacy. But when Hogan was assassinated in a car bombing in 1928, the system began to unravel. The rise of the FBI, the end of Prohibition, and the arrival of notorious gangs like the Barker-Karpis crew—led by Ma Barker and her sons—eventually exposed the cracks in the system. The FBI’s use of fingerprint technology and public pressure from business leaders led to the collapse of the O'Connor system in 1935, ending 36 years of criminal sanctuary. The episode blends dark humor with historical depth, painting a portrait of a city that traded moral compromise for safety, and questioning whether such a system could ever work in modern times.