May 16, 1895, Detective Wooldridge, accompanied by Officers Kern, O'Connor and Cameron, located Matt Kelly at 411 State street, who was wanted for a criminal assault. Kelly was a hold-up man, ex-convict and a notorious safe-blower, who several years prior to this shot two officers in St. Louis, Mo. Kelly was found behind locked doors on the second-floor and refused to open the doors. Detective Wooldridge went to the adjoining flat, opened a window and crawled along the ledge until he had reached Kelly's room; with a revolver in his mouth he pushed up the sash and was faced by Kelly and his wife.
"Go back or I'll kill you," said Kelly as he pushed his revolver in Wooldridge's face.
Wooldridge had meanwhile secured a good hold on the sill of the window, but was not in a position to defend himself. The Kelly woman tried her best to shove him off; she succeeded in loosening one of his hands, and for an instant Detective Wooldridge thought he would have to fall. With an almost superhuman effort Wooldridge broke in the window and covering Kelly with his own revolver ordered him to throw up his hands, which he did. He was taken to the police station and heavily fined.
A Plot to Kill Detective Wooldridge.
A dozen of the highwaymen and robbers on whom Wooldridge was waging a relentless warfare gathered together on the morning of July 4, 1895, and formed a plot to kill Wooldridge and get him out of the way. They concluded that the night of July 4, when everyone was firing off revolvers and celebrating, would afford the best opportunity. They imagined it would be an easy thing to shoot him from one of the windows or from a housetop while he was on duty patrolling his post, and no one would know where the shot came from, as there was shooting from every direction.
An oath of secrecy was taken by all present, and lots drawn to see who was to do the deed. In all probability their plan would have been carried out had it not been for a colored woman, who was watching them and heard the whole plot, and who went with the information to the Harrison Street Police Station.
Captain Koch and Lieutenant Laughlin were notified and upon investigation found the report to be true. They took immediate steps to protect Wooldridge by placing three additional officers in full uniform with him, and also placing six men in citizen's clothes on his post. Every man they met was searched for a gun; every crook, vagrant and thief that they could lay their hands on was placed under lock and key in the station, and by 11 o'clock that night there was no square in the city quieter than the one this officer patrolled, and in two weeks' time "Coon Hollow" and the whole neighborhood for half a mile in every direction had undergone the most remarkable change known to police history, and this change was apparent for a long time thereafter.
February 11, 1896, Detective Wooldridge, while trying to arrest a panel-house keeper and three colored hold-up men at 412 Dearborn street, was fired upon by one of the trio, Kid White, the shot striking the bar of his watch chain, which was attached to the lower button of his vest. When the bar was struck the bullet was diverted from entering Wooldridge's stomach, and it glanced off and passed through his overcoat.
Detective Wooldridge Roughly Handled.
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.