Feature Chicago Detective

Find out more about Clifton Wooldridge.

Chicago Detective

The name Clifton Wooldridge means little to people today, but to Chicagoans and Chicago criminals, he was notorious.

Wooldridge, a former police officer was described at the time as "the incorruptible Sherlock Holmes of America," and he was on a mission to save Chicago from itself. 

He considered Chicago the "wickedest city in the world." It certainly had the right ingredients. Chicago was seen as the land of opportunity, or at least the gateway to it. People passed through on their way to homesteading further west, the railroad brought folks to the city, in the hopes they would find one of the many possible jobs in this burgeoning city. It became a hotbed for vice and corruption. 

As a police officer on the beat, Wooldridge saw what was happening. He battled everything: quack doctors, prostitution, gambling, investment swindles, insurance scams, fake banks, clairvoyants and marriage agencies. He associated with the down and out and the richest of the rich. Apparently he would stop at little to learn the ways of the criminal. Wooldridge was adept at disguising himself, and would dress for the part, whether it meant posing as a rube in from the country or even donning black face. 

In 1906, after 20 years on the police force, he proudly proclaimed a record of 19,500 arrests, with 3,200 criminals locked up, 6,000 people paid fines, 100 girls rescued from prostitution, $100,000 worth of property recovered, and 100 marriage bureaus closed. 

His wrote numerous books detailing crimes he'd witnessed in the sincere hope of preventing further victims. Titles included: Hands Up! In the World of Crime," and "The Devil and The Grafter and How They Work Together to Deceive, Swindle and Destroy Mankind." 

Wooldridge was a man on a mission, intent on stopping further people from falling prey to thieves. He wrote a list of tips called "Detective Clifton R. Wooldridge's 'Never-Fail' System for Detecting and Outwitting All Classes of Grafters and Swindlers." 

Some of his tips included:

  • "When a man tries to hurry you into spending your money put it back in your pocket and keep your hand on it."
  • "If the promoter could do one-half of what he claims he would not need your money, but soon would be rich beyond the dreams of avarice."
  • "Industry, energy, thrift! These are the dice that win."

While his books read like the pulp fiction popular at the time, they also provide an unparalleled look into the criminal underworld of Chicago.