Hidden City Crime Files: Chicago

In this Hidden City Crime File we look at 3 stories from the city of Chicago ... H.H. Holmes, John Dillinger and the 1968 Democratic National Convention Riots.
Cities are more than brick and concrete. They are made of stories. And the best stories are usually about the worst people. Thriller novelist Marcus Sakey goes from city to city to identify 3 crimes or criminals who reveal the dark undercurrent of that city. In Hidden City's Crime Files we take a look at the stories featured for each city. We start with Chicago.

The Devil in the White City: H.H. Holmes
Chicago History Museum

Chicago History Museum

Photo by: Chicago History Museum

Chicago History Museum

Who: Dr. Henry Howard Holmes was born Herman Webster Mudgett. He was born on May 1, 1861, in Gilmanton, NH. His father was known to be a violent alcoholic and his mother was a religious woman who read him the Bible. His parents punished him and his siblings by locking them in an attic for a full day of silence and no food. Herman left home at 19 and went on to attend medical school.

What: Dr. Holmes was one of the first American serial killers. He also committed fraud by taking out life insurance on his employees and then collecting the premiums for accidental death when, in reality, he killed them. While it is not known how many people he murdered, estimates are between 4 and 200. He tortured and asphyxiated his victims and would then cremate or sell off their skeletons and organs.

Where: Holmes built what neighbors referred to as “the Castle” in the Englewood area of Chicago. It was a 3-story building that had offices, a drug store, shops and more than 100 windowless rooms. The building was opened as a hotel for the World’s Columbian Exposition in 1893. This was also the site of his murders.

When: Holmes built “the Castle” in the late 1880s and killed many of his victims there in 1893, during the World’s Fair. In 1894, Holmes fled Chicago and tried to execute more insurance fraud by faking the deaths of his associates. Holmes was eventually arrested in Boston in November 1894. Following Holmes' arrest for horse theft, he was eventually traced by the authorities him back to the Castle; they soon discovered the death chambers and corpses. In May 1896, Holmes was hanged for his crimes.

In the Media: Many books and movies have been done on H.H. Holmes. Erik Larson's The Devil in the White City is the best-known book on the topic while the documentary H.H. Holmes: America's First Serial Killer has won many awards. Both Tom Cruise and Leonardo DiCaprio have been tied to Holmes projects.

Dapper and Deadly: John Dillinger



Photo by: New York Daily News Archive

New York Daily News Archive

Who: John Herbert Dillinger was born on June 22, 1903, in the Oak Hill section of Indianapolis. His mother died when he was young and his father was a harsh disciplinarian. His father remarried and John resented his step-mother.

What: Throughout his childhood John got into trouble. After robbing a grocer he received an excessive sentence and went to prison. This experience hardened him and precipitated his crime spree of robbing banks. During one of their robbery he killed a police officer. In addition, Dillinger stole a
sheriff’s car during one of his jail escapes and drove across state lines, a federal offense.

Where: John Dillinger and his gang members robbed banks in Illinois, Ohio and Indiana.

When: Dillinger was released from prison in May 1933 after serving 8 1/2 years for his grocery robbery. Dillinger simply resumed his reign of crime. It ended when the FBI ultimately they tracked him down in Chicago. While trying to flee from agents, Dillinger was killed outside the Biograph Theater on July 22, 1934.

In the Media: Many books and movies have been made about John Dillinger's life. He has been portrayed by Leo Gordon, Warren Oates, Robert Conrad, Mark Harmon, Martin Sheen and Johnny Depp.

Civil War in City Streets: The Chicago 7
 'News crews interview American activist Jerry Rubin (1938 - 1994) outside the 1968 Democratic National Convention, Chicago, Illinois, August 1968. Rubin, who founded the Yippees political party, and six others, called the Chicago Seven, were indicted for conspiracy and inciting a riot during the convention. (Photo by Hulton Archive/Getty Images)'


'News crews interview American activist Jerry Rubin (1938 - 1994) outside the 1968 Democratic National Convention, Chicago, Illinois, August 1968. Rubin, who founded the Yippees political party, and six others, called the Chicago Seven, were indicted for conspiracy and inciting a riot during the convention. (Photo by Hulton Archive/Getty Images)'

Photo by: Hulton Archive

Hulton Archive

Who: Abbie Hoffman, Jerry Rubin, David Dellinger, Tom Hayden, Rennie Davis, John Froines, and Lee Weiner were known as the Chicago 7. They were leaders from various anti-war groups who were charged with inciting a riot at the Democratic National Convention.

What: More than 15,000 protesters demonstrated against the war during the Democratic National Convention. They were stopped by police with tear gas, mace and clubs. The Chicago 7 were said to have planned the violence all along. Ultimately 2 of them were acquitted and the other 5 were found guilty and sentenced to 5 years and $5,000 in fines. These convictions were later overturned due to issues with the jury.

When: The anti-war rally was held on August 28, 1968, and the violence lasted 5 days.

Where: The only permit that the city granted was for a rally in Grant Park. After that demonstration many of the protesters tried to march on the International Amphitheatre and were stopped by police outside the Conrad Hilton Hotel.

In the Media: Several films have been released about the riots and the Chicago 7. Writer Aaron Sorkin wrote a script called The Trial of the Chicago 7. Steven Spielberg was going to produce it and had gotten Sacha Baron Cohen, Heath Ledger and Will Smith to star. The project stalled with a Writers Guild of America strike and has not moved forward since.

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