Detective Wooldridge, from March, 1898 until April 5, 1907, was attached to the office of the General Superintendent of Police and worked out of his office. During that time over 1,200 letters and complaints were referred to him for investigation and action.
He has personally arrested 19,500 people, 200 of them were sent to the penitentiary; 3,000 to the house of correction; 6,000 paid fines; 100 girls under age were rescued from lives of shame; $100,000 worth of property was recovered; 100 panel houses were closed; 100 matrimonial bureaus were broken up.
The Chicago Tribune of November 25, 1906.
WHO IS LIKE A DETECTIVE IN A STORY BOOK THE PHOTOGRAPHS POSED FOR THE TRIBUNE BY DETECTIVE WOOLDRIDGE SHOW HIM IN VARIOUS DISGUISES
Chicago may be surprised to learn that it has a Sherlock Holmes of its own, but it has. Furthermore, hw is where a Sherlock Holmes belongs, on the staff of the superintendent of police”working from”the central detail of detectives. His name is Clifton R. Wooldridge, and before his actual experiences in crime hunting in the city of Chicago, met with in the day’s work and regarded as mere incidents. the fictional experiences through which Poe, Doyle, and the omnipresent Nick Carter put their detective heroes pale into insignificance.
Truth is stranger even than detective fiction. No author working sixteen hours a day, dreaming his plots while he slept, could hope in the short span of years allotted mortal man as a life to equal in strangeness, improbability, thrills, excitement, and number in his fiction the real experiences of Detective Wooldridge in real life.
Twenty Years a Detective
By Clifton R. Wooldridge
As Chicago’s official Sherlock Holmes Wooldridge has been face to face with problems that make “The Sign of the Four” look childish. He has handled successfully cases wherein the criminal was more untraceable than the gorilla who committed the murders in “The Rue Morgue.”
Outrivals the Heroes of Fiction.
He has been in danger in ways which, compared to Nick Carter’s favorite stunt of being tied up in a gunny sack and pitched into the murky waters of the East river while the villain says: “Curses on him; he is done for at last!” are as football is to pingpong. And In the number of his adventures of mystery, danger, and excitement he has all the detective heroes of fiction and reality beaten easily.
He has arrested in his sixteen years of experience as Chicago taker 19,500 people.
Of this mass of arrests 200 have resulted ia sending some law breaker to the penitentiary, 3,000 to the house of correction, and of the remainder of those arrested at least G,000 have paid. Through them 100 girls under age have been rescued from lives of shame, $100,000 worth of stolen property has been recovered, 100 panel houses closed, 100 matrimonial bureaus broken up, and the same number of opium dens wiped out of existence. In making them Wooldridge has refused 500 bribes, ranging from $500 to $5,000.
As “Policy” Sam Johnson of South State Street
An illustration of the way the detective employs himself in the gambling dens. It is often necessary to play and lose money in these places that he may get at the facts. Observe that he is watching proceedings in another part of the room while he is throwing the dice.
Record in Rrief of Detective Wooldridge.
He has been under fire forty-four times. He has been wounded dozens of times.
He has impersonated almost every kind of character met with in a cosmopolitan city, from the visiting farmer to the Italian ragpicker.
He has, in his crime hunting, associated with members of the 400 and the inhabitants of the levee.
He has handied small talk with the leaders of fashionable society and fraternized with hobos.
He has dined with the elite, and he has smoked in Clark street opium dens. All In all, the story of his adventures would fill several volumes. Further, they do fill volumes, this detective being his own chronicler.
He has done everything that one expects the detective of fiction to do, and which the real detective seldom does, and many other things beside. At the same time he Is on the police pay roll as a detective sergeant, and “works from” the central detail much like any other detective assigned to the staff of the general superintendent.
Man of Many Disguises.
If you happen to be in the vicinity of central detective headquarters In the city hall any morning, between 9 and 10, you may see a quiet little man with a sharp face and grayish mustache enter the general superintendent’s office. Ten minutes later, perhaps, a disreputable negro of the roll neck sweater, crap shooter variety may shamble forth, or, perhaps, a fur coated stock man who obviously is just in from the stockyards, where he had disposed of a load of steers, may walk out, or It may be a ragpicker who appears. But if any of these characters does come out it will be quite useless to enter the superintendent s office and seek the quiet little man with the sharp features.
The quiet man who entered Is Detective Sergeant Wooldrldge. The negro, stock man, or ragpicker who comes out Is also Detective Sergeant Wooldridge. He simply has put on one of his numerous disguises. He has effected a complete metamorphosis in the ten minutes he was in the office. Chicago’s Sherlock Holmes has begun his day’s work.
Various Disguises of Detective Wooldridge
(From Left) “Heck” Houston, a Stock Raiser of Laramie, Wyoming, a Man of the Ghetto, an Englishman and as a Man of Society
Changes That Would Astonish an Actor.
Not tnat Wooldr!dge continually prowls about the streets of the city In disguise. But when occasion requires that he cease to appear as Wooldridge and appear as somebody quite different he can make the change so quickly and effectively that even an actor would be astonished. It matters not what the part he must play, gilded youth or negro gambler, honest farmer. or lodging house “bum,” it requires, but a few minutes for this present day Lecocq, who does, the work of a Sherlock Holmes and a dozen policemen combined, to “make up:’
Chicagoans accustomed to regard their detectives merely as officers in plain clothes would be astounded to see the disguise equipment of Detective Wooldridge, watch the way in which he manipulates it, and follow him when, in disguise, he goes forth to run to earth elusive wrongdoers.
If their sense of humor is developed to a trouble-some degree they might be moved to laughter at the array of whiskers, wigs, burnt cork, rubber, fur coats, wide hats, old shoes, “comedy pants,” fake wallets, stage money, cheap jewelry, and other things that go to make up the outfit, for the idea of a Chicago detective using such paraphernalia in his day’s work is startling, and a “makeup” usually is amusing.
But when it is known that it is mainly through the use of these same makeups and the pursuit of the sleuth methods that go with them that Wooldridge has been able to pile up this amazing record of 19,500 arrests it becomes apparent that, while extremely theatrical, such means must be efficient in the same degree.
Effective Methods of Work.
While the traditional detective of with his disguises and his sensational methods is as far from the real city detective as the hero of a musical comedy is from a real man, yet in Wooldridge he has his counterpart in real life, The makeup, the convenient closet into which the detective hides and hears the perpetrator of a crime boast of his guilt to his confederates, the barrel for a hiding place, and all the rest of it are of common usage to this Chicago police officer. As material for a fiction writer he would be a gold mine—only he writes his own stories and collects his own royalties.
For Instance, where could be conceived the fancied tale superior to the true one of how Wooldridge gathered evidence to convict the keeper of a disorderly house on Thirty-first street? For originality and unique features this exploit has few equals in of detective wiles and devices.
Securing Evidence in One Case.
Complaints had been made at the Stanton avenue station for several weeks concerning the establishment, but try as they would uniformed officers were helpless so far as securing evidence enough to convict was concerned, Wooldridge, at that time a uniform 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 a 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 it excited no suspicion In the minds of those in the flat, and Wooldridge, with his sleuth’s eye at one af the holes, saw what served to drive the place out of existence and secure the conviction of its keeper.
While the transition from aeronaut to high diver is a strange one, it was not impossible to Detective Wooldridge. To offset this aerial stunt he took a high dive from the top of a building, landing on his head In a pile of refuse with such force as to go “in over his
head,” and stick there so tightly that It required the combined strength of two officers to pull him out by the legs.
It was near Twelfth and State streets while pursuing two women across a roof that this remarkable stunt took place. The women jumped from the roof Into a pile of refuse. They landed on their feet. Wooldridge came after them. He landed on his head. As ho landed he grasped a woman with either hand, and held them until the arrival of his brother officers effected his release and their capture.
But these are only humorous incidents, things to laugh over when the day s work is done. In the parlance of the detectives they belong to “straight work.” As a direct antithesis to them there is the story of the murder and the black cat which is in real life a weirder and more startling affair than Poe’s fantastic tale of the same subject. A black cat helped solve a murder in a way which puts a distinct strain on the credulity of the uninitiated.
WOOLDRIDGE’S CABINET OF BURGLAR TOOLS
At the police headquarters in Chicago, one of the most attractive curios is the above cabinet of burglar-tools and weapons taken by Detective Wooldridge from robbers and crooks during his eighteen years of service.
Story That Rivals That of the Black Cat.
A rich man had been murdered In a certain part of the city. He was in his library at the time of the crime, his family was in an adjoining room, yet none of them heard any noise, or knew what had been done until they found him lifeless on the floor. Investigation proved that he had been shot, but not with an ordinary weapon. The missile in his heart was a combination of bullet and dart, evidently propelled from a powerful air rifle or spring gun. But no clew was left by the perpetrator of the crime, and Wooldridge carried the strange missile in his pocket for several months before a single prospect of apprehending the murderer appeared. Then it was the black cat that did it. By what strange coincidence or freak of fate it was that impelled -the cat to literally lead the detective to a little pile of dirt in an alley that nignt Wooldridge never has attempted to explain. But lead him it did, when he dug into the disturbed ground he found something entirely new in the gun line, the weapon that had discharged the fatal bullet he had in his pocket. Eventually he traced the gun to its inventor, and from there to the man who had purchased it, a young fellow named Johnson, and a supposed friend of the murdered man’s family. The sequence was that this man proved to be the murderer. When arrested he at first denied his guilt, broke down under the sweatbox ordeal and confessed, and killed himself in his cell next morning. For mystery and good fortune in bringing an apparent- ly untraceable criminal to justice this incident perhaps has never been equaled in Chicago’s Police records.
Remarkable Worle as Rag Picker.
Perhaps his appearance in the role of a ragpicker. 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 for 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 corns, a curly wig, a bag, and 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 spells. 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.
Hero of Some Fierce Fights.
Presently Lane and Reed appeared and went south on State street. Wooldridge followed, and at an opportune moment seized them both from behind. The fight that followed is historic. Only sheer luck and the threat to kill both of his antagonists on the spot if they did not cease resistance saved the detective’s life. After knocking both men with his billy he succeeded in holding them until a fellow officer came to his rescue.
But Wooldridge’s 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 saved him. He finally managed to shoot 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 Wooldrldge was left alone by them for a long, long time.
Fine Work in a Thieves’ Resort.
Disguising himself as a cheap, thief, entering a Clark street criminals’ resort, and fraternizing with thieves, murderers, and vagabonds of all kinds in order to obtain information led Wooldridge into the most school of crime ever witnessed by a Chicago police officer. He was accepted in good faith as a proper sneak thief by the brotherhood, and for fhis benefit the “manager” of the den put his “pupils” through their “lessons.” The lessons were in shoplifting, pocket picking, purse snatching, and other forms of larceny requiring skill and deftness. When he had seen enough Wooldridge generously volunteered to “rush the growler,” and went out—and called the patrol wagon. Twenty-three crooks were arrested this time, each one of whom swore he would have killed the detective had his makeup or conduct for an instant directed suspicion toward him.
This was shortly after a negro, firing point blank at him from a distance of four feet, had struck his watch chain, which, diverting the course of the bullet, had saved him from having a hole made through his heart.
Fooling the Sports at a Cock Fight.
Using a pair of old, decrepit roosters as adjuncts to crook taking savors of the burlesque, but such a move once helped WooldrIdge land a gang of roughs who engaging in the pleasant diversion of chicken fighting. Arrayed as a bum he went to a poultry store, purchased his two “fightun’ chickens,” and with them in a bag made his way to the neighborhood where he knew the fight was to take place. Inquiring for the whereabouts of the place where he claimed to have been sent to deliver the “fighters,” he was directed to an old. abandoned building. Here he was admitted, and, after leaving his bag with one of the promoters of the main, he pretended to go out for more birds. MWhen he returned he was Detective Wooldridge, and a patrol wagon load of officers was at his back.
Literally speaking, the darkest situation into which his experiences have led him was the tunnel by which inmates of Mattie Lee’s famous resort at 150 Custom House place when the place was raided. Mattie had decided that it was a nuisance to go to the station every time the police wanted to arrest her, so she had the tunnel dug. After that when the police called on her Mattie greeted them with an empty house and a sweet smile, while underground the inmates were crawling on their hands and knees to safety. Wooldrldge found the tunnel, and, crawling in, “snaked out” six colored men and women whom he found in the darkness. Versatility is a requisite with the successful detective.
Boys Are Worst Customers to Handle.
But after all, this man of many wonderful experiences admits that the hardest people to arrest are not the ones who are experienced in the ways of crime.
“The 17 or 18 year old kid with three or four beers in him is the worst customer for the police to handle,” he says. “An old criminal usually is too wise to use a gun on a detective. But the embryo bad man, half drunk and thoroughly excited, is the bad one. He isn’t afraid to kill, because he doesn’t know what it means to be wanted for murder. He thinks be can shoot and get away. Of course he can’t, but that doesn’t make it any safer for the officer arresting him. He will pull a trigger where an older robber would surrender. He’s a problem, and the job of handling him is the worst that the officer meets with.”
Just what the Sherlock Holmes would do with this class of criminal is problematical. It is something that he never went up against.
The special detail under charge of Officer Clifton R. Wooldridge, operating from the office of the General Superintendent, has punished and put out of business scores of matrimonial bureaus and agencies, turf investment concerns, home building associations, bucket shops, lotteries, wire tappers, fake promoters, book agencies and miscellaneous concerns.
General Superintendent of Police
Report of the General Superintendent of Police· of the
CITY OF CHICAGO TO THE CITY COUNCIL FOR THE FISCAL YEAR ENDING
December 31. 1903