The Bourbon King, The Inside Story: The Birth of a Bootleg King

How did George Remus become “Bootleg King?” What drove him to criminality—Hubris? Greed? Love of alcohol?

George Remus moved decisively into bootlegging.

As Remus’s legal career flourished, he became celebrity in Chicago, then nationally. [I like to joke that he was kind of the Johnnie Cochran of early twentieth century Chicago.] The fame and money were not enough to satisfy his desires — he expected to become a larger than life figure. Remus thought of himself in almost presidential terms, as if he were anointed to greatness.

Remus began defending small-time Windy City bootleggers in his law practice. Like court employees, attorneys, and probably even the judges themselves, George looked on bemused when these hoodlums would pay fines by pulling large rolls of cash out of their pockets and quickly counting out huge sums of money. Rolls of hundreds…

Legend has it that Remus realized if the two-bit thugs could make thousands of dollars, then he could use his intelligence to make millions.

As a top defense attorney, George’s annual salary reached more than ten times the cost of the average home in America, but he wanted more…more fame, money, and the toys the good life made possible.

Remus had no moral position on bootlegging or breaking the law. He often claimed to be a teetotaler, but many witnesses could have testified to that standing as yet another Remus “little white lie.” He liked to share a stiff drink and a fat, black cigar with friends, despite the public histrionics about not drinking liquor.

George needed to play intellectual games to justify his positions on various issues. For example, he believed that acting outside the bounds of decorum in court battles was okay, because doing so enabled him to spare his clients the death sentence. The end goal made the means of attaining it justified in his mind.

Similarly, Remus didn’t think Prohibition was a just cause. His early attempts at bootlegging in Chicago proved that enforcement was difficult and that people would continue to demand liquor, regardless of the law.

George also knew that the money would give him power and influence. He set out to exploit the loopholes in the Volstead Act as a way to fulfill the flashy life he dreamed of…and his young paramour Imogene Holmes yearned for her entire life.

The Bourbon King, The Inside Story: George Remus as a High-Flying Defense Attorney

George Remus became a top criminal defense attorney in Chicago. What made him so successful in the courtroom?

George Remus transitioned to attorney at a time when the Chicago economy boomed and new residents poured into the region. His early work centered on labor law, representing several large Windy City unions. The efforts put George in the circle of famed attorney and human rights activist Clarence Darrow.

Both men abhorred the death penalty and Remus gravitated to criminal defense work, just as Darrow had done earlier in his career. What set George apart was his willingness to do anything to win, particularly if he could get a death row sentence reduced to jail time.

When Remus put his considerable intellectual and physical efforts toward a legal career, he ruffled the existing “old boy’s network,” which saw him and his second-rate legal training as an imposition on the establishment they had crafted (he most likely faced a great degree of anti-German discrimination as well). George charged ahead, though, engaging in local Republican politics and serving as a leader in a new legal society aimed to upend the status quo.

No one could deny Remus’s dedication, but his tactics upset many of his colleagues.

George Remus photographed during his time as an attorney in Chicago

If a legal eagle were Remus’s friend, he might refer to George as the “Napoleon of the Bar” as a way of acknowledging his legal acumen. Others, however, called George “weeping pleading Remus,” because his theatrics were viewed as outside the bounds of decorum.

George’s escapades were legendary—from starting fistfights with opposing counsel to drinking down poison in front of the jury to proved his client not guilty (luckily, George had mixed up the antidote and taken it beforehand). Many of Remus’s trials were covered by reporters regionally and nationally. Chicago Tribune journalists knew they could call on George for a hot soundbite.

Although Remus might wildly gesticulate and fly into near rages to defend a client, jurors also remarked about how mesmerizing Remus was in the courtroom. George seemed to have a sixth sense regarding when a well-time antic might persuade a jury or distract them from the prosecution’s case. He possessed a natural charisma and magnetism that defined his legal career.