Image: “Dapper Dan” Hogan (Public Domain)

On this day in history, December 4, 1928, “Dapper Dan” Hogan, a St. Paul, Minnesota bar-owner and mob boss, is assassinated when an unknown assailant places a car bomb underneath his new Paige coupe. Doctors labored all day to save his life – wrote the Morning Tribune, “racketeers, police characters, and businessmen” lined up at the hospital to donate blood to their stricken friend – but Hogan fell into a coma and died about 9 p.m. His murder remains unsolved.

Hogan was the leader of the Twin Cities criminal world. His downtown bar, the Green Lantern, catered to bank robbers, bootleggers, safecrackers, and all-around thugs. On top of money laundering, he was proficient at resolving petty disagreements, preventing disputes from getting out of hand, and (the Morning Tribune stated) “keep[ing] the heat out of town,” which made him a friend to a great many criminals and a valued asset to people (like the corrupt-but-well-meaning police chief) who were attempting to keep Minneapolis and St. Paul from turning into being as blood-stained and hazardous as Chicago.

Hogan and the police acted to ensure that criminals would be secure in the Twin Cities if they committed their most horrendous crimes outside the city limits. This made him a great many friends – “his word was said to have been ‘as good as a gold bond,’” the paper declared, and “to numbers of persons he was something of a Robin Hood” – but it also infuriated many gangsters who disliked his monopoly on the city’s rackets. Police believed some of his associates might have been to blame for his assassination.

In 1909, Hogan settled in Saint Paul, where he soon uncovered his true calling – arranging a major criminal network from the refuge of St. Paul, choosing the correct criminal people for the task, and laundering stolen commodities, specifically difficult-to-fence Government bonds. During this period, Hogan’s close friend and associate, mob-affiliated St. Paul Police Chief John O’Connor, allowed lawbreakers and outlaws to work in the city as long as they touched base with Hogan, paid a small inducement, and promised not to kill, rape, kidnap, or rob within the city’s boundaries.

Even though Hogan himself often bypassed this rule, his crimes almost always garnered significant profits and very rarely included the use of firearms. Hogan also became a fixer strongly tied to the Democratic Party that ran St. Paul, which also caused police officers to fear him, which caused them to safeguard his organization actively. The U.S. Department of Justice tried several times to prosecute him but was always unsuccessful.

Hogan also functioned as an “ambassador” for Chief O’Connor and visiting gangsters from the National Crime Syndicate. Hogan owned the Green Lantern bar on Wabasha Street, St. Paul, an illegal gambling casino and a speakeasy during the Prohibition era. Hogan prepared armed robberies in the towns close to the Twin Cities and casino gambling and money laundering in the Minneapolis-St. Paul area.

On December 4, 1928, Dapper Dan entered his Paige coupe and turned on the ignition. A bomb located beneath the floorboards exploded and tore off his right leg. He went into a coma at the hospital and died nine hours later.

Complimented by $5,000 worth of beautiful flowers sent by gangster colleagues from the Twin Cities, Chicago, and New York City, Hogan was given a funeral suitable for Prohibition-ers Chicago. He was interred in Calvary Cemetery in St. Paul’s North End. After the memorial service, Chicago North Side Gang leader Bugs Moran stood guard outside the Hogan family home at West Seventh Street to protect his dead friend’s family from additional incidents.

However, the mobster’s widow, Leila Hogan, stated, “I am sure there will be justice. If Danny had lived, he would have gone on the one leg they left him and taken care of it himself.”

Although the murder is still listed as unsolved, the most likely person responsible, according to FBI files, is Lithuanian Jewish mobster and long-time Hogan associate Harry Sawyer.

According to interviews his ex-wife Rita Sawyer gave to the FBI, Harry Sawyer felt that Hogan had finagled him out of a $36,000 portion from an illegal gambling casino they co-owned at the Hollywood Inn in Mendota, Minnesota. Harry Sawyer also paid $25,000 towards Hogan’s bail in 1927 after the boss had been charged with planning the 1924 robbery of $35,000 from the Chicago Great Western Railroad depot at South St. Paul. To Sawyer’s eternal anger, Hogan had never reimbursed him.

Hogan was aware of who killed him but never told his family because he feared the gangsters would come after them.

Hogan’s murder is particularly noteworthy because it was one of the first times in the National Crime Syndicate that a car bomb was used to assassinate a crime boss. After the funeral, Lithuanian Jewish Gangster and former Hogan ally Harry Sawyer and his associate, crooked police chief Big Tom Brown assumed Hogan’s former status as the boss of St. Paul’s underworld. Together they organized a vicious crime spree that would have disgusted Danny Hogan. Their collaboration with both the Dillinger and Barker-Karpis Gangs caused some of the most notorious crimes of the Depression era, resulting in the expansion of the Federal Bureau of Investigation under J. Edgar Hoover.

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