For mystery and good fortune in bringing an apparently untraceable criminal to justice this incident perhaps has never been equaled in Chicago's police records.
On Duty in Great Strike.
In 1900 Chicago's great building trade strike occurred in which 60,000 men were thrown out of employment. Many acts of violence were committed. Several men were killed and many maimed and injured.
Detective Wooldridge was placed in charge of thirty picked detectives from the detective bureau with orders to suppress these lawless acts and arrest the guilty offenders. Through his vigilance and untiring efforts law and order were soon restored, and he was highly complimented by Chief of Police Joseph Kipley and the public press.
Literally speaking, the darkest situation into which his experiences have led him was the tunnel by which inmates of Mattie Lee's famous resort at 150 Custom House place escaped when the place was raided. Mattie had decided that it was a nuisance to go to the station every time the police wanted to arrest her, so she had the tunnel dug.
After that when the police called on her Mattie greeted them with an empty house and a sweet smile, while underground the inmates were crawling on their hands and knees to safety. Wooldridge found the tunnel and, crawling in, "snaked out" six colored men and women whom he found in the darkness. Versatility is a requisite with the successful detective.
Remarkable Work as a Ragpicker.
May 28, 1905, perhaps, his appearance in the role of a ragpicker, which led to the arrest and conviction of two negro highwaymen, Henry Reed and Ed Lane, was his most daring and successful effort at disguise. Lane is at present serving a life sentence in Joliet for the murder of Robert Metcalfe.
The assault and robbery of a contractor named Anderson was the occasion for Wooldridge's assumption of the guise of ragpicker. Anderson had described Lane so accurately that the detective was sure of recognizing him once he put his eyes upon him, but in those days a detective to go into the black belt looking for a criminal was to spread a wide alarm over the whole district. Consequently he "made up." A pair of large, worn overalls, a coat three sizes too large, a bunch of papers between his shoulder blades to give him a hunch back, burnt cork, a curly wig, a bag and a piece of telegraph wire, and the erstwhile shrewd-looking detective was in ten minutes the typical negro ragpicker who shambles up and down alleys on the south side in hope of picking up enough for his day's bread.
While thus pursuing his way Wooldridge not only discovered the presence of Reed and Lane, but actually worked through the refuse in a garbage box upon which Lane was sitting quarreling with some confederates over the division of the previous night's spoils. He even went so far as to pick up an old coat which Lane had discarded. Thereupon Lane ordered him to get out of the alley or get his throat cut from ear to ear. Wooldridge went humbly out, and waited.