In August, 1890, complaints had been made at the Stanton Avenue Police
Station for several weeks concerning the establishment of a disorderly
house at 306 Thirty-first street, but try as they would uniformed
officers were helpless so far as securing evidence enough to convict
was concerned. Wooldridge at that time a uniformed man, was put in
plain clothes and detailed on the case. One of the great stumbling
blocks in the way of the police had been the high basement under the
house, which made it impossible for any one to look in the windows of
the flat without the aid of the ladder. As the presence of a ladder
would arouse suspicion, the problem of viewing the inside of the flat
was a difficult one.
One thing the other men on the case had overlooked. This was the
presence of a beam jutting out from the top of the building to which
a rope, pulley, and barrel were attached, used as a means of lowering
garbage and ashes from the second floor to the alley. Wooldridge saw
the possibilities of the rope and barrel trick. Attaching to the rope
a vinegar barrel with holes bored in it at convenient intervals, he
awaited an opportune time, curled up in the barrel, and had himself
drawn up to the level of the windows by two officers. The lowering and
raising of the barrel being a customary thing in the building, excited
no suspicion in the minds of those in the flat, and Wooldridge, with
his sleuth's eye at one of the holes, saw what served to drive the
place out of existence and secure the conviction of its keeper.