Stunning vintage photos document one of the most notorious eras in American crime

In the early 20th century, Chicago was one of the most crime-ridden places in America. After the passage of Prohibition, in 1920, powerful gangs of bootleggers, gangsters, and smugglers formed to profit from illegal alcohol trafficking. Al Capone, Bugs Moran, and John Dillinger and their gangs became household names that were equal parts criminals and celebrities.

The Chicago Tribune, one of the preeminent newspapers at the time, was there to photograph it all, including the ruthless criminals who ruled the Chicago underworld and the hero policemen who brought them down. The Tribune recently opened its archives for a new book, “Gangsters & Grifters: Classic Crime Photos from the Chicago Tribune,” which shows the paper’s photos from the era. Agate Publishing has agreed to share some of those photos with us here, and you can check out the rest in the book.

John Dillinger was one of the most notorious bank robbers and gangsters during the Depression. As media reports detailed his daring exploits, he became increasingly famous, eventually being named “Public Enemy No. 1.” Here, Dillinger (center) is handcuffed to Deputy Sheriff R. M. Pierce during a court hearing in Crown Point, Indiana, in 1934. Dillinger was charged with killing police officer William O’ Malley during a bank robbery in East Chicago, Indiana, a month earlier.

This photo shows the county jail at Crown Point as Dillinger arrived on January 30. Because of fears that his gang would try to rescue Dillinger, heavily armed guards surrounded the courthouse. Before Dillinger could stand trial in March, he would break out of the jail with a wooden gun.

On March 8, 1931, 1,500 convicts at Stateville Prison in Crest Hill, Illinois, rioted, setting multiple buildings on fire. Here, state policemen retake control of the facility. Numerous buildings in Stateville, like this one, were designed according to the “panopticon” concept championed by philosopher Jeremy Bentham.

In the photo below, Richard Loeb (left) and Nathan Leopold (right) stare at each other after confessing to the kidnapping and killing of 14-year-old Robert “Bobby” Franks on May 21, 1924, in Chicago. The duo were wealthy students from the University of Chicago who said they killed Franks to commit the “perfect crime.” It was called “the crime of the century,” and both Loeb and Leopold gained fame.

George Stathatos was a tavern owner and gambler in Chicago during the 1940s. He was suspected to be part of a gang that robbed crime-syndicate handbooks, which listed prominent members in gangs as well as listing of bribes. Here, his sister, Agnes Stathatos, cries after identifying George’s body. He was found in his car with two bullets in his head, apparently killed in retaliation.

Rose Neary was found dead in her apartment on June 2, 1939. She was strangled by a radio cord in her kitchen, before a towel was placed over her head and she was hit with a claw hammer. Though her murder was never solved, police suspected her chauffeur, Edward Donovan, who owed her $US2,000 from a loan.

On April 28, 1929, off-duty Chicago policeman Sidney Block, seen here, shot a fashionably dressed gunman who had held up two nearby stores. Block reportedly told the gunman to stop as he drew his gun. The robber refused, telling Block to “Go to hell!”

Grace Druggan was the wife of Terry “Machine Gun” Druggan, an Irish-American bootlegger and crime boss. Grace is seen here in court on March 7, 1941, to get custody of her 3-year-old son. The two had a custody agreement that allowed Druggan to see the boy on the weekends, but one week he refused bring him back. Grace Duggan committed suicide in 1946.

William Heirens was known as “The Lipstick Killer.” In 1946, he was convicted of kidnapping and killing 6-year-old Suzanne Degnan. Heirens was also convicted of murdering Frances Brown, 33, and Josephine Ross, 43 in 1945. Heirens got his nickname because he wrote, “For heaven’s sake, catch me before I kill more. I cannot control myself,” on the wall of Brown’s apartment in lipstick. He is seen in this photo surrounded by Detective Chief Walter Storms on his left and Captain Michael Ahern on the right.

In this photo 22-year-old Gertrude “Billie” Murphy is being brought in for questioning in the murder of Michael Stopec in 1927. Supposedly, Stopec and the person suspected of killing him, Henry Guardino, were rivals for Murphy’s affection. Before the murder, Murphy had told Guardino that she was leaving him in favour of Stopec.

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