Detective Wooldridge from March, 1898, until April 5, 1907, was attached to the office of the General Superintendent of Police and worked out of his office. During that time over 1,200 letters and complaints were referred to him for investigation and action.
April 5, 1907, Detective Wooldridge was relieved of this work and transferred, and crusade and extermination of the get-rich-quick concerns ceased.
September 20, 1889, Detective Wooldridge was placed in charge of twenty-five picked detectives, who were placed in charge of the suppression of hand-books and other gambling in Chicago. He remained in charge of this detail for three years.
On December 13, 1890, at the residence of Charles Partdridge, Michigan avenue and Thirty-second street, while three desperate burglars were trying to effect an entrance into the house, Detective Wooldridge espied them and in his attempt to arrest them was fired upon by the trio. One shot passed through his cap, clipping off a lock of his hair and grazing his scalp. The next shot struck him squarely in the buckle of his belt, which saved his life.
Numberless Hair-Breadth Escapes.
August 20, 1891, he met with another narrow escape at Thirtieth and Dearborn streets, while attempting to arrest Nathan Judd, a crazed and desperate colored man. Judd threw a brick at him, striking him over his left temple, and inflicting a wound two inches long.
Judd was shot through the thigh, and afterwards was sent to the house of correction for one year.
Detective Wooldridge, alone in a drenching rainstorm at 4 o'clock on the morning of June 23, 1892, at Michigan avenue and Madison street, intercepted three horsethieves and hold-up men in a buggy trying to make their escape.
At the point of a revolver he commanded them to halt. As they approached him no attention was paid to him, or to what he was saying. Seizing the bridle of the horse, he was dragged nearly a block before the horse was checked. A twenty-pound horse weight was hurled at him by one of the robbers, which just missed his head. Another one of the robbers leaped upon the horse and rained blow after blow upon his head with the buggy whip.
Detective Wooldridge shot this man in the leg; he jumped off the horse and made good his escape while Wooldridge was engaged in a desperate hand to hand encounter with the other two robbers. Wooldridge knocked both senseless with the butt of his revolver. They were taken to the police station and gave their names as John Crosby and John McGinis. Both were found guilty a month later and sent to the penitentiary by Judge Baker.