A Bootlegger's Story - The Night Run

Here's an imaginary story that captures the dangerous and exciting life of a bootlegger.

Note:  A bootlegger was an illegal alcohol distributor during the Prohibition period in the United States (1920-1933), when the manufacture, sale, and transportation of alcoholic beverages were banned by the 18th Amendment. The term "bootlegger" originally came from the practice of hiding liquor bottles in the tops of boots, but it evolved to describe anyone involved in smuggling and distributing illegal alcohol.

And so the story goes... Tommy Malone waited nervously in his Ford Model A, while the engine purred in the night. In the trunk were cases of Canadian whiskey, hidden beneath a layer of potato sacks.

It was 1927 and prime time for prohibition where the liquor trade was both dangerous and lucrative. Tommy was running booze for a group of speakeasies across Los Angeles. Working underground bars was his life. He was paying top dollar for each case of smuggled alcohol. It was lucrative and a single run could net him $5,000, which was considered a fortune during the Great Depression.

Tommy planned the route carefully. He knew the back roads and where potential police checkpoints were. He also had a team of lookouts as well as corrupt cops.  Tommy modified his car with reinforced suspension to handle heavy loads and it was also equipped with hidden compartments to stash extra liquor.

Approaching the city limits, Tommy signaled with a pattern of headlight flashes to give his contacts a heads up. Speakeasy owners would be ready and waiting to stock their hidden bars. The money they paid was worth it as patrons paid top dollar for a single drink.

The risks were certainly huge and if caught, Tommy could face serious jail time. Especially considering federal agents, local police, and rival bootleggers all posed constant threats. Not only would Tommy’s car be confiscated, but his network exposed. Even worse, he could be killed, either by law enforcement or competing smuggling gangs looking to control territory.

It was a tough trade off. Because the money was great and it was too good to resist. Tommy worked with a local distillery that produced moonshine, supplementing it with imported Canadian and European liquor smuggled across the border. There was a steady stream of demand from local speakeasy owners, including a few run by gangsters,

Payment was always in cash, and the transaction was often in a pre-arranged location. No receipts, no paper trail. A handshake and a stack of bills was how they handled their business. Speakeasy owners marked up the liquor by 500% or more and it made everyone in the supply chain wealthy. 

As Tommy approached the back entrance of O'Malley's speakeasy, he knew another one of his bootlegger runs was almost over. As before, he whispered the password, the hidden door opened and the deal was done.