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.