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Crime & Curiosities

From obscure police blotters to forgotten scandals and surprising incidents, revisit the peculiar occurrences that dotted the city's past.

When the Speakeasy Burned: A Forgotten Fire and Foul Play in Prohibition-Era Chicago

The Mystery of "Whispering Willie," The City's Most Elusive Pickpocket (1920s)

When the Speakeasy Burned: A Forgotten Fire and Foul Play in Prohibition-Era Chicago

When the Speakeasy Burned: A Forgotten Fire and Foul Play in Prohibition-Era Chicago

Dr. Vivian Holloway - Dec 22, 2025

The Mystery of "Whispering Willie," The City's Most Elusive Pickpocket (1920s)

The Mystery of "Whispering Willie," The City's Most Elusive Pickpocket (1920s)

Maeve O'Connell - Nov 19, 2025

The Rise and Fall of Detective O'Malley: Corruption in the Early 20th Century Police Force

The Rise and Fall of Detective O'Malley: Corruption in the Early 20th Century Police Force

Elias Vance - Nov 12, 2025

The City's First 'Social Media Scandal': When Gossip Columns Led to Duels (and arrests)

The City's First 'Social Media Scandal': When Gossip Columns Led to Duels (and arrests)

Dr. Vivian Holloway - Nov 3, 2025

Anatomy of a Blotter: A Day in the Life of the 1920s Vice Squad

Anatomy of a Blotter: A Day in the Life of the 1920s Vice Squad

Arthur "Art" Sterling - Oct 31, 2025

The Truth Behind "The Phantom of Park Avenue": Was It a Ghost or a Clever Thief? (1930s)

The Truth Behind "The Phantom of Park Avenue": Was It a Ghost or a Clever Thief? (1930s)

Leo Maxwell - Oct 21, 2025

When the Opera House Became a Crime Scene: A Look Back at the 1912 Poisoning Scandal

When the Opera House Became a Crime Scene: A Look Back at the 1912 Poisoning Scandal

Arthur "Art" Sterling - Oct 18, 2025

The Peculiar Case of the 1897 "No Loitering with Intent to Whistle" Ordinance

The Peculiar Case of the 1897 "No Loitering with Intent to Whistle" Ordinance

Elias Vance - Oct 18, 2025

On This Day, 1934: The Great Bakery Heist and the Case of the Missing Croissants

On This Day, 1934: The Great Bakery Heist and the Case of the Missing Croissants

Elias Vance - Sep 24, 2025

After the Great Fire: How the City's Underworld Rebuilt (and Thrived) in the Ashes of 1871

After the Great Fire: How the City's Underworld Rebuilt (and Thrived) in the Ashes of 1871

Maeve O'Connell - Sep 19, 2025

The Great Unsolved Jewel Heist of 1903: A Downtown Legend

The Great Unsolved Jewel Heist of 1903: A Downtown Legend

Leo Maxwell - Sep 19, 2025

Meet 'The Pigeon Whisperer of Park Row': A Century-Old Scam Artist

Meet 'The Pigeon Whisperer of Park Row': A Century-Old Scam Artist

Arthur "Art" Sterling - Sep 18, 2025

The Case of the Vanishing Vaudeville Star: A 1920s Theatrical Mystery

The Case of the Vanishing Vaudeville Star: A 1920s Theatrical Mystery

Dr. Vivian Holloway - Aug 23, 2025

The Ghost of Astor Place: Unraveling an 1890s Unsolved New York Burglary

The Ghost of Astor Place: Unraveling an 1890s Unsolved New York Burglary

Arthur "Art" Sterling - Jul 31, 2025

Lost Labyrinths: Unearthing the Secret Speakeasies Beneath the Old Grand Hotel (Demolished 1950)

Lost Labyrinths: Unearthing the Secret Speakeasies Beneath the Old Grand Hotel (Demolished 1950)

Leo Maxwell - Jul 20, 2025

The Phantom of the Old Market: Unraveling a Century-Old Local Legend

The Phantom of the Old Market: Unraveling a Century-Old Local Legend

Leo Maxwell - Jul 10, 2025

When Speakeasies Ruled: The Hidden Architecture of Prohibition-Era Downtown

When Speakeasies Ruled: The Hidden Architecture of Prohibition-Era Downtown

Maeve O'Connell - Jul 8, 2025