For Chicagoans who craved hooch during Prohibition, Dean O’Banion was a savior. He and his mob, the North Side Gang, controlled nearly all the alcohol coming into the city. By 1921, the bootlegger was raking in millions, and the papers were calling him “Chicago’s Arch Killer.” And then O’Banion made an unexpected career move: He got married and started running Schofield’s flower shop near Navy Pier.

It wasn’t a complete 180—O’Banion initially bought an interest in the shop so he could use the upstairs room as a headquarters. But he also had a genuine soft spot for floral arranging and spent a lot of his time on the shop floor. Plus, floristry and organized crime had lucrative synergies. Mob etiquette demanded that gangsters spend thousands of dollars on funeral arrangements, and thanks to O’Banion’s connections, Schofield’s quickly became the premier flower shop of the mafia world. Even O’Banion’s enemies brought him their business. Al Capone—the North Side Gang’s arch nemesis—once ordered an $8000 rose funeral sculpture from him.

But O’Banion’s fortunes wilted in November 1924. After he insulted a member of Capone’s South Side Gang, a hit was ordered. Longtime southsider Mike Merlo had just died of cancer, giving Capone’s henchmen an innocuous reason to visit Schofield’s. Three hoods walked into the shop and shot O’Banion dead while he trimmed chrysanthemums for the funeral. When O’Banion’s body was found, he was still holding the scissors. The murder sparked a five-year gang war that led to approximately 600 casualties, coincidentally peaking on a day known for its floral arrangements in the infamous St. Valentine’s Day Massacre.

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