Early in the evening of April 10, 1928, the day of Chicago’s municipal primary, a candidate for alderman named Octavius C. Granady was pulling up to a polling station, choked with voters fresh from work, when a man dressed in a gray overcoat and a fedora strolled up to his car, drew a pistol, and fired a volley of shots through the back window. Amazingly, the would-be killer missed his target. Granady’s driver slammed his foot on the gas, sending the vehicle, hung with campaign banners, burning rubber down Washburne Avenue. The gunman hopped onto the running board of a nearby Cadillac, which promptly gave chase.
The weeks leading up to the city’s election had been marked by a frenzy of political violence. Chicago’s flamboyantly amoral mayor, William “Big Bill” Thompson, who had recently won office on the populist slogan “America First,” enjoyed the backing of local gangsters, including the infamous syndicate kingpin Al Capone. To push through Thompson’s ticket of loyal supporters, Capone’s henchmen adopted a blunt approach to canvassing. Houses of political officials were bombed, poll workers beaten, and the citizenry intimidated by club-wielding thugs. Tabloids dubbed the election the Pineapple Primary—“pineapple” being slang for a hand grenade.
A brave coalition of civic reformers, however, was fighting back against the corruption afflicting the city. Among them was Octavius Granady. A Black lawyer and World War I veteran, Granady had volunteered to run against a longtime Thompson ally named Morris Eller, who was white, for the city council seat representing Chicago’s 20th Ward. The heavily contested race soon became the front line in the battle for the soul of the city. Fearing for his life as primary day approached, Granady had asked for protection from the police department. The request was denied.
After the attempt on his life, Granady’s car careened wildly for more than a mile through the crowded streets of the South Side, trying desperately to lose its pursuers. The hitman, still hunched low on the running board and clutching the Cadillac’s steel frame for balance, continued to snap off rounds. Then, while trying to maneuver a turn, Granady’s driver lost control and crashed into a curb.
Dazed, the candidate stumbled from the wreck, only to be met by a trio of attackers exiting the Cadillac. Squaring up, they brought him down in a spray of shotgun fire. As Granady lay dying, the assassins sped off, a banner for his opponent flapping from their vehicle’s chassis.
Nearly a decade into Prohibition, Chicagoans had become inured to a certain amount of murder and mayhem. But the daylight execution of a principled political reformer shocked the populace. A special prosecutor was appointed to bring the perpetrators to justice. His first task was to hire someone to lead the investigation into the killing—someone fearless and independent, free from influence by the city’s notoriously troubled police department. A series of reputable investigative agencies, however, failed to make any headway in the case. Frustrated, the prosecutor turned to an unlikely choice—a Black man, one who had been blazing an extraordinary path through the world of criminal investigation: Sheridan Bruseaux.
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