In 1896 Wooldridge's fiercest fight came when he arrested George
Kinnucan in his saloon at 435 Clark street. A dozen roughs, henchmen
of Kinnucan, who were in the saloon at the time, came to the
saloonkeeper's rescue. The officer was knocked down, his billy taken
from him and himself beaten unconscious with it, and his face and
head kicked into one mass of bruises. Through it all he managed to
hang on to his revolver. This alone saved him. He finally managed to
shoot Kinnucan through the hand and forearm, and a moment later a
uniformed man burst in and evened up the battle. Six of the toughs
were arrested, and Wooldridge was left alone by them for a long time.