Ep 12. Underground Bootleggers: Portland, Oregon

In the twelfth episode of the first season of "Cities of the Underworld," the viewers are taken on an exploration of the city of Portland, Oregon, where they uncover the little-known history of underground bootleggers. The episode titled Underground Bootleggers: Portland, Oregon, explores the city's seedy past during the Prohibition era, where local criminals ran secret bars, speakeasies, and distilleries in the city's underground tunnels and basements.

The episode begins with host Don Wildman setting the scene for viewers by exploring Portland's underground tunnels, showcasing their dark and mysterious atmosphere. He then goes on to explain the context of the Prohibition era and how it affected the city. With a rising demand for alcohol and a lack of legal options, bootleggers seized the opportunity to make a fortune by producing and selling illegal alcohol. The episode highlights the illicit activities of Portland's bootleggers and some of their most notorious characters.

Wildman takes viewers through Portland's underground city, where bootleggers operated secret bars, also known as speakeasies, during Prohibition. He reveals how these underground locations were hidden from authorities and were only accessible through a network of secret entrances and tunnels. The episode touches on some of the notorious customers who frequented these establishments, including rumrunners, gangsters, and even celebrities.

In addition to illegal bars, bootleggers also ran illegal distilleries in Portland. The episode delves into how these bootleggers transported their illegal products through the underground tunnels and how they managed to evade authorities. Wildman explains that many of these tunnels were used by legitimate businesses in the past and were often left abandoned. Bootleggers seized this opportunity and used these tunnels to transport their illegal products and avoid detection by the police.

Apart from the speakeasies and distilleries, the bootleggers in Portland also operated underground gambling dens. Wildman explores how these establishments were organized and the types of games that were played, including poker, dice games, and even cockfighting. The show also explores the tension between rival gangs who competed for control over the various illegal businesses and territories.

Throughout the episode, Wildman breaks away from the underground setting to explore some of the historical landmarks of Portland that are connected to the city's bootlegging past. He visits buildings that once housed hidden speakeasies and distilleries that are now open to the public. The episode ends with Wildman exploring the impact of the Prohibition era on Portland's social and cultural history and how it continues to shape the city today.

In summary, the twelfth episode of the first season of "Cities of the Underworld" titled Underground Bootleggers: Portland, Oregon, explores the underground world of bootlegging during the Prohibition era in Portland. The episode highlights the illegal activities of bootleggers who ran secret bars, distilleries, and gambling dens underground, and their impact on the city's social and cultural history. Wildman takes viewers through the dark and mysterious tunnels of Portland's underground city, providing insight into the hidden world of bootlegging.