Crown of Shadows: The Prohibition King's Rise and Fall (part 1)

Transport yourself to the smoky speakeasies of 1920s Chicago, where one man seized the chaos of Prohibition to build an empire unlike any other. He wasn’t a household name, but his cunning rivaled the most infamous crime lords. From a humble start, he rose to wealth and power, manipulating the law with brazen genius and a twisted loyalty to himself alone. This two-part episode uncovers the legend behind a bourbon bottle you might have overlooked, a story pulsing with ambition, betrayal, and a ruthless thirst for dominance. Join us as we dive into the shadowy world of this Prohibition king, a figure history nearly forgot.

This story is the favorite of my guests out on the Bourbon Trail.  It is a story that many guests have asked how this story has not been made into a movie.  I have no answer, as it would make an incredible movie. 

There is so much to this story, I decided to split it into two parts.  I hope you enjoy!

Thank you for listening to Bourbon: Legends from the Trail, where history meets flavor and every bottle has a story to tell. Cheers to the stores and legends behind the Spirit! Please leave a rating and review as it will help me plan future episodes.

Transcript

Take a moment and let your mind travel back in time to a smoky Chicago speakeasy, jazz thumping through the floorboards, and powerful men defying Prohibition with every sip. It’s the Roaring Twenties, and the nation is trapped under the iron grip of the Volstead Act. Alcohol is outlawed, yet the thirst for it is insatiable.

While many of you are thinking it, this isn’t Al Capone’s tale. Today, I’m unveiling a name history nearly forgot. A man who built an empire in the shadows—without the fame, but with every bit of the ruthlessness. His rise was meteoric, his fall catastrophic.

In a world of forbidden whiskey and backdoor deals, he was more than a player—he was a king. Ambition fueled him, power consumed him, and betrayal shattered him. His story is full of dark ambition and deadly consequences. As you have perused the bourbon aisle of your favorite liquor store, you have likely seen this bottle of bourbon and passed it by, not knowing the legend that is hidden behind his steely eyes on the label of a bourbon bottle that sits there on the shelf, just waiting to tell its tale. This story is my guest's favorite while out on the trail and many times I am asked why this story has not been made into a movie.  My answer is “I have no idea, because what a movie it would be”.

So, buckle up. This is the story of George, a legend from the trail you won’t soon forget.

So….whether you got a glass in hand and a cozy spot to relax as your listen or you are weaving this story into the rhythm of your busy day, prepare for another LEGEND…straight from the heart of Bourbon’s past.

Welcome to Bourbon: Legends from the Trail….where history meets flavor and every bottle has a story to tell

Our story today, begins with George.  George was born in Germany in 1878, but by the time he was four, his family had immigrated to America, landing first in Milwaukee and then settling in Chicago. Even as a boy, George had a spark of brilliance—and a determination that few could match. At a very young age, he would tell anyone who was listening “George will be the first in the family to speak fluent English, and sure enough, anyone who ever spoke with George marveled at his mastery of the language. But his father, who may have been intelligent, must have lacked that same dogged determination, you see he struggled with the language which kept him from keeping steady work. This frustration led anger and then the anger led to abuse, abuse of alcohol, and finally, physical abuse of his family.. George saw his father’s self-destruction and vowed, “George will never drink alcohol, because George does not want to end up like George’s father.” And anyone who ever was around George said they never saw him drink a drop of alcohol.

And if you have not noticed yet, George had a curious habit—he always spoke about himself in the third person. It became a signature quirk that would follow him throughout his life. As George was smart and determined he  excelled in school, but the family’s financial struggles forced him to drop out by age 14 to help support them. He took a job sweeping floors and stocking shelves at his uncle’s pharmacy (his uncle who had been a pharmacist in Germany and had come to America a couple years after George’s family) Many nights, George was known to sleep at the store, likely to get away from his father’s abusive tirades.  This choice of going to work for his uncle would plant the seeds for his eventual rise to power. George, always with an eye out, noticed that his uncle made a pretty good living for himself.  So George decided that he would be a pharmacist just like his uncle. 

Driven by that ambition, George applied to the Chicago school of Pharmacy and was accepted because at this time you only needed to pass the entrance exam. George, with his wit and grit, finished ahead of schedule, and by age 19, not only was he a licensed pharmacist, but he owned not one but two pharmacies in Chicago. Also around this time, he also met a young woman named Lillian, and they eventually married and had a daughter, Romola, who would later find fame herself as an actress, playing Dorothy in the 1908 black-and-white version of The Wizard of Oz. But while George had built a life that many would envy, it wasn’t enough. You see George had a fire inside him that couldn’t be extinguished by mere success. No, he had a growing addiction and it wasn’t alcohol or drugs—it was money and fame. 

His life took a sharp turn when he noticed a new breed of customer coming through his pharmacies: men dressed in sharp, pinstriped suits, flashing gold watches, and draped with glamorous women. He was intrigued, and George began inquiring as to what these men did for a living, and soon learned that many of the men were lawyers.  George quickly realized that being a lawyer, “That is where the money is at”. So, ever the overachiever, he applied to the Chicago school of Law and was accepted.  He began a three-year degree, going to school mainly in the evening as he worked at the pharmacy during the day. George, with his overzealous determination, finished the degree in just 18 months, graduating at the top of his class and passing the bar exam on the first try.  And in 1902, at age 24, he became the youngest member of the Illinois Bar Association.

But George didn’t want to just practice any type of law. He did not want to do family law, and he did not want to do real estate law. They were much too boring for him. George wanted the drama, the thrill—he wanted cases that would make headlines. He knew he needed to become a trial lawyer, specializing in high-stakes murder cases. His hatred for the death penalty drove him to defend clients facing execution. Those people in and around the law quickly learned that George was not just your average, ordinary lawyer. The courtroom you see, became his stage as he was known to be extremely dramatic and theatrical in court. Many claimed that George didn’t just argue cases—he performed them. It was written that George would run around the courtroom flailing his arms, leap onto chairs and jump off, throw himself down on the floor, yell, scream, anything he could do just to make his point to the judge and jury. His theatrics had the courtroom buzzing, and soon, he wasn’t just a lawyer—he was a spectacle.

Another drastic turning point occurred in George’s life in 1914, when he defended a man named William Cheney Ellis, a man who with his wife Eleanor were upper echelon socialites in Cincinnati. Ellis was a man accused of murdering his wife, in a high-society scandal that gripped Chicago. You see Ellis believed that his wife was having an affair and when she said she was going to visit a friend in Chicago, he thought for sure she was going to meet her lover. The evidence was damning for Ellis. William Ellis had been found in a hotel room in Chicago, standing over his dead wife with the murder weapons in his hands.  He claimed that it was a suicide pact between them.  Eleanor had been shot twice and her throat sliced.  Ellis himself only had a bullet to the leg.  Ellis claimed that he had failed in his attempt at killing himself. All seemed lost for Ellis as everyone in Chicago knew he was for sure to get the death penalty.  However, George pulled a rabbit out of his hat. He was doing his usual thing, yelling, screaming, running around the courtroom and then he stated that his client was so in love with his wife, that the mere thought of her betrayal had caused a mental break, that his client had suffered a moment of (and here is your coined term)  “transitory insanity,” Between George’s theatrics in the courtroom and this new term, transitory insanity, the jury ate it up, and Ellis was spared the death penalty. Ellis was sentenced to 14yrs in prison of which he served 7 before getting out on good behavior.  But the bigger picture here was George.  Overnight, George became a national sensation—newspapers and magazines from New York to Los Angeles began running articles on this young Chicago attorney and Transitory Insanity.  George, you see, had just become the inventor of the “insanity defense.”

But with all this new fame came darker decisions. George had met a young woman and began an affair. Her name was Imogene, remember that name. It was a relationship that ultimately ended his marriage to Lillian. Imogene was wild and carefree, She loved attention and money as much as George and frequently referred to him as Daddy. As the years rolled on, George’s ambitions grew bolder. By 1920, he was one of the most successful lawyers in Chicago, pulling in $50,000 a year (which is the equivalent of $800,000 a year in today’s money). But then, the Volstead Act was passed and Prohibition hit like a thunderclap. Many of George’s new clients were men on trial for violating the prohibition laws.  For most, it spelled disaster. But for George, it was the catalyst for another career change.

One fateful day in court, George was defending a man accused of violating Prohibition laws. The case was presided over by Judge Kennesaw Mountain Landis, notorious for handing out harsh punishments and fines. As George was putting on his normal dramatic show, defending his client, something unexpected happened. The client came up behind George and tapped him on the shoulder. “May I speak to the judge?” he asked. George, being caught off guard, turned to Judge Landis who nodded that it was OK. George sat down at the defense table and watched. The large gallery in the courtroom tuned in, in silence. The man approached the bench and asked Landis, “Judge, Are you going to render me guilty?” The judge replied, “I am.” He then asked “Well, Are you going to give me a large fine?” “I absolutely am,” Landis said with a smirk. Then the man said, “Well how much is your fine going to be?”  Landis leaned over the bench, smiled at the man and said “$10,000”. The courtroom gasped at the incredibly large fine. The defendant paused, stared into the judges eyes, then slowly reached into his pocket. He pulled out a wad of cash so thick that he could barely fit in his hand around it. He counted out ten stacks of $1000 in each on the judge’s bench, turned and walked over to George at the defense table, and counted out 10 more stacks of $1000 in each.  He then winked at George, turned with a smirk of his own back at the judge, and then tipped his hat and walked out of the courtroom, free as a bird.

George, like the rest of the courtroom, was stunned. As he watched his client walk out of the courtroom door, his mind began to spin with possibilities. And at that moment he later recalled, that… was where the money was at. He went on to say that  at that very moment, George decided George would build the largest empire of illegal booze the world had ever seen. In order to do it, George knew that he would have to find ways to get around the Volstead Act.

George, now became consumed by the intricacies of the Volstead Act, he studied it like a sacred manuscript and discovered two CRUCIAL loopholes. First, while the Act prohibited the manufacture, sale, or transportation of alcohol, it said nothing about the sale of warehouse receipts for liquor that was already secured in federally bonded warehouses. Armed with this knowledge, George devised his plan. He knew distilleries were collapsing under the pressure of Prohibition, so with his deep pockets, he knew he could purchase the distilleries, giving him access to the rickhouses along with the receipts. Once in his possession, this liquor became his personal property—and it would be out of the government’s reach.

The second loophole was pure genius. Six distilleries had been permitted to sell medicinal alcohol, and as long as someone selling it had a medicinal license, they could sell the alcohol. And, wouldn’t you know it, what was George before he was a lawyer…..that’s right, he was a pharmacist and had his medicinal license. 

His next move would be to buy out these distilleries and funnel the alcohol through his real pharmacies and a network of fake ones he would create. This legitimate front was only half the story. Behind the scenes, George crafted an elaborate scheme. He hired a crew of 80 men to intercept shipments of his own liquor—stealing approximately 90% of his shipments. The twist? He would collect the insurance payouts for the stolen shipments, only to sell the ‘stolen’ liquor on the black market. In his own words, “George decided to rob George to pay George,” dubbing this ingenious strategy “The Circle.”

But George had another crucial decision to make: where would he launch his empire? Staying in Chicago would mean competing with crime kingpins Johnny Torrio and Al Capone, something George wasn’t keen on. Instead, he looked around for a large city, on that’s current law enforcement was easily bribed, and had a local bootlegging scene that was amateur compared to what George had in his mind. As he looked around, he discovered a place. It was strategically positioned within a 300-miles of 80% of the world’s bourbon supply. That place was Cincinnati, OH. So he and his wife Imogene and her daughter Ruth, moved to Cincinnati, ready to build his empire.

Next week on Bourbon: Legends from the trail, part 2 of Crown of Shadows: The Prohibition King’s Rise and Fall

“As George’s journey takes him to Cincinnati, he steps into a world where wealth and corruption go hand in hand. Surrounded by marble, gold, and opulence, he quickly rises to be the King of the Underworld. But his ambition and charm have their limits—and cracks begin to show, not only in his empire but in his marriage to the captivating yet dangerously impulsive Imogene. With powerful friends in high places and enemies lurking in the shadows, George’s world spirals into chaos as the authorities close in.

In Part 2, we’ll dive into George’s empire at its peak: the splendor, the deception, and the alliances that led to the legendary party that inspired a classic novel. But as the saying goes, all empires will fall. Betrayal, forbidden passion, and a high-stakes game of revenge bring George’s world crashing down, leading to one of the most sensational murder trials of the century. Will the King of Bootleggers escape unscathed, or will justice finally catch up to him? Join us for Part 2, where legends rise and fall in a blaze of glory.”

1.  The Bourbon King: The Life and Crimes of George Remus, Prohibition's Evil Genius by Bob Batchelor.  Diversion Books.  2019.
2. King of Bootleggers: A Biography of George Remus by William A. Cook. McFarland 2008
3. Cincinnati's Most Notorious Bootlegger by Library Staff, Cincinnati Public Library, Jan. 7, 2021