GEORGE REMUS created and ran a massive bootlegging empire responsible for much of the country’s booze supply during Prohibition. Unlike the mob bosses featured here, he was more of a businessman than a gangster, but I’m including him because he was a true criminal pioneer and one of the most fascinating organized crime figures of his era. Famous for his excessively lavish parties, Remus is often credited as the inspiration for the titular character of The Great Gatsby.

Prior to his criminal career, Remus was a highly successful and well-known Chicago trial attorney, pioneering the “temporary insanity” defense. After noticing that many of his criminal clients were amassing wealth through the illegal alcohol trade in the 1920s, Remus decided to become a criminal himself, using his knowledge of the law to stay one step ahead of the authorities.

With gangsters already controlling bootlegging in Chicago, Remus established his operation in Cincinnati. He began with a single distillery in 1920, establishing his own trucking company to transport his product. With his brilliant aptitude for business, his small empire quickly boomed, and within three years, the operation had over 3,000 full-time employees. At his peak it’s estimated that he supplied about one-seventh of the nation’s alcohol. Already well off from his law career, Remus would amass over 40 million dollars from bootlegging, which is the modern equivalent of about 700 million.

For a time, Remus stayed immune to prosecution thanks to hundreds of thousands of dollars paid in bribes. But as his empire reached outlandish heights, he became a target of the federal Prohibition Bureau. In 1925, Remus held a series of meetings to work out logistics of his operations, but his hotel suite was bugged. Found guilty of bootlegging, he was sentenced to two years in federal prison at age 47.

Remus tried to resume his lucrative bootlegging business upon his release, but found that violent gangsters had taken over his empire, so he moved to Kentucky and opened up a real estate office. He remained a legitimate businessman the rest of his days, dying of natural causes at age 74.