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. HERO OF SOME FIERCE FIGHTS. Presently Lane and Reed appeared and went south on State street. Wooldridge followed, and at an opportune moment seized them both from behind. The fight that followed is historic. Only sheer luck and the threat to kill both antagonists on the spot if they did not cease resistance saved the detective's life. After knocking both men down with his billy he succeeded in holding them until a fellow officer came to his rescue. They were arrested and convicted June 25, 1905, and sent to the penitentiary for three years. May 19, 1906, Detective Wooldridge raided the following places: H. C. Evins, 125 S. Clark street; George Deshone, 64 N. Clark street; E. Manning Stockton, Bar & Co., 56 Fifth avenue, seizing some $30,000 worth of gambling paraphernalia. Disclosures of conditions which so seriously threatened the discipline of the United States army and navy that the secretaries of the two departments and even President Roosevelt himself were called upon to aid in their suppression. It was charged that a coterie of Chicago men engaged in making and selling these devices had formed a "trust" and had for years robbed, swindled and corrupted the enlisted men of the army and navy through loaded dice, "hold-outs," magnetized roulette wheels and other crooked gambling apparatus. CROOKED GAMBLING TRUST.