“Dapper Dan” Hogan, a St. Paul, Minnesota saloonkeeper and mob boss, is killed on December 4, 1928 when someone plants a car bomb under the floorboards of his new Paige coupe. Doctors worked all day to save him–according to the Morning Tribune, “racketeers, police characters, and business men” queued up at the hospital to donate blood to their ailing friend–but Hogan slipped into a coma and died at around 9 p.m. His murder is still unsolved.

Hogan was a pillar of the Twin Cities underworld. His downtown saloon, the Green Lantern, catered to (and laundered the money of) bank robbers, bootleggers, safecrackers and all-around thugs. He was an expert at defusing petty arguments, keeping feuds from getting out of hand, and (the paper said) “keep[ing] the heat out of town,” which made him a friend to many lawbreakers and a valuable asset to people (like the crooked-but-well-meaning police chief) who were trying to keep Minneapolis and St. Paul from becoming as bloody and dangerous as Chicago.

Hogan and the police both worked to make sure that gangsters would be safe in the Twin Cities as long as they committed their most egregious crimes outside the city limits. If this position made him more friends than enemies–“his word was said to have been ‘as good as a gold bond,'” the paper said, and “to numbers of persons he was something of a Robin Hood”–it also angered many mobsters who resented his stranglehold on the city’s rackets. Police speculated that some of his own associates might have been responsible for his murder.

As the newspaper reported the day after Hogan died, car bombs were “the newest form of bomb killing,” a murderous technology perfected by New York gangsters and bootleggers. In fact, Hogan was one of the first people to die in a car bomb explosion. The police investigation revealed that two men had entered Dapper Dan’s garage early in the morning of December 4, planted a nitroglycerine explosive in the car’s undercarriage, and wired it to the starter. When Hogan pressed his foot to that pedal, the bomb went off, nearly severing his right leg. He died from blood loss.

The first real car bomb–or, in this case, horse-drawn-wagon bomb–exploded on September 16, 1920 outside the J.P. Morgan Company’s offices in New York City’s financial district. Italian anarchist Mario Buda had planted it there, hoping to kill Morgan himself; as it happened, the robber baron was out of town, but 40 other people died (and about 200 were wounded) in the blast. There were occasional car-bomb attacks after that–most notably in Saigon in 1952, Algiers in 1962, and Palermo in 1963–but vehicle weapons remained relatively uncommon until the 1970s and 80s, when they became the terrifying trademark of groups like the Irish Republican Army and Hezbollah. In 1995, terrorists Timothy McVeigh and Terry Nichols used a bomb hidden in a Ryder truck to blow up the Alfred P. Murrah Federal Building in Oklahoma City.