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.