Jake Lingle, a prominent reporter for the Chicago Tribune, was shot dead at the Illinois Central train station in Chicago in a brazen act of violence during rush hour. The gunman, Leo Vincent Brothers, allegedly carried out the assassination on behalf of gangster Al Capone, who reportedly had a significant gambling debt of $100,000 owed to him. Lingle was known for his connections and stories involving organized crime, making him a controversial figure in the Chicago journalism landscape. His murder raised both alarm and intrigue among the public and within the media industry, as it exemplified the pervasive influence of organized crime in American cities during this period.

The murder occurred in broad daylight, shocking commuters and citizens alike. Brothers fled the scene but was soon captured and linked to the crime. The police investigation revealed the extent of the corruption that plagued the city, with many officials being either complicit or too frightened to take a stand against the criminals. The implications after Lingle’s murder reverberated through Chicago’s media and law enforcement communities, prompting deeper scrutiny into the ties between reporters and mobsters that characterized the Roaring Twenties.

In the wake of Lingle's assassination, democracy in press freedom was called into question, as journalists struggled between reporting on crime and protecting their own safety. Lingle became a symbol of the dangers faced by reporters in a city dominated by gangsters and corruption, sparking conversations on the ethics of journalism and its implications on society.