‘Sherlock Holmes of Chicago’
19,500 arrests and dozens of gunfights? The legendary claims — and ego — of Clifton R. Wooldridge
According to no less an authority than the Chicago Tribune, Detective Clifton R. Wooldridge was the “Sherlock Holmes of Chicago.” An eager promoter of his own legend who was aided by the press, Wooldridge was a boon and a nuisance to his superiors, a hero and an affliction to his family, and a guardian and a menace to the public.
As a patrolman, then a detective and finally on special assignment as a fraud investigator, Wooldridge came under fire 44 times, suffered dozens of wounds, made 19,500 arrests, refused 500 bribes, recovered as much as $200,000 in stolen property, broke up 125 matchmaking agencies and saved 100 underage girls from living in shame, among other feats and dangers. Or so he bragged — with the enthusiastic help of the Tribune.
He also claimed to be a master of disguise — though some of his costumes played on laughable stereotypes, with at least one involving blackface. Among his characters were an Englishman, a “man in the ghetto,” “Policy” Sam Johnson of South State Street and the piece de resistance: “Heck” Houston, a cattleman from Wyoming, with the detective looking ridiculous in a shaggy fur overcoat, a flat-brimmed white cowboy hat, a full white beard and a mustache as wide as his shoulders.
Criminals “fall ‘easy game’ to the detective thus disguised,” Wooldridge’s autobiography trumpeted.
In the books he published between 1901 and 1918, Wooldridge recounted his derring-do: the “numberless hair-breadth escapes”; the “fierce fights”; a discovery to rival Edgar Allan Poe’s “Black Cat”; a “superhuman” vault from a windowsill to capture a desperado; a headfirst leap from a roof into a trash pile to snare a female suspect in each hand; and on and on. They read like dime novels — and were about as plausible.
Such was the legend of Clifton R. Wooldridge. The reality, as it often is, was more complicated and less inspiring.
A native of Kentucky, Wooldridge served in the Army and prospected in Colorado before coming to Chicago around 1887. He worked first as a railroad switchman, then became a police officer in 1888 and rose quickly to detective.
Wooldridge’s name started popping up in the Tribune in 1892: That January, he was one of the first officers on the scene of a hotel fire and was credited with carrying a mother and her children to safety. Then in August, a rabid cat, of all things, earned him more newspaper ink. Responding to a call of a family’s pet going berserk, Wooldridge cracked the parlor door at the home “cautiously,” the Tribune wrote, “and shot the cat while it was climbing up the wall.”
In his first years as a detective at the Harrison Street station, Wooldridge pursued the common run of bookies, thieves, swindlers, robbers, con artists, pickpockets, cheating merchants, and backroom poker players and dice shooters. Among the rogues he tracked down was a band of burglars that stole 72 boxes of chewing gum from a factory on Wabash Avenue, the Tribune reported.
Wooldridge’s reputation as a fearless crusader for justice grew — and along with it, his ego — with his appointment as a special investigator, taking on the fortuneteller cons, the lonely hearts rackets, the wildcat insurance operators and the toogood-to-be-true investment scammers.
The press and the police brass gloried in his victories. “I can say this for Wooldridge,” Chief Francis O’Neill said in 1904 after censuring the detective for bad judgment, “in the last eight or nine months more get-rich-quick schemes that were fattening off the people of Chicago have been driven out of business than ever before in the same length of time.”
The Tribune published a photo gallery of the celebrated detective’s disguises in 1906. It also gave him space in the paper to educate the public. In a short piece titled, “Big Ring of Grafters Prey on the Public,” Wooldridge informed readers that the nationwide take from frauds of all kinds totaled $150 million a year. “The victims are numbered among all classes,” he wrote, “from the laundress to the lawyer, the merchant to the clergyman.”
A couple of months later, he announced his decision to stop writing books. Instead — sounding disturbingly like the hucksters he kept his eye on — he planned to sell by mail courses in the methods of police investigation, as well as a badge, for $15.
Even Wooldridge’s foibles were treated with indulgence. In 1907, he arrested a dealer for selling reproductions of “improper” art “portraying women in various stages of attire and some in no attire at all,” the Tribune reported. Questioned by the judge, he admitted that the dealer’s wares were “not the worst of it” and threatened to raid the Art Institute and “destroy or have clothed some of the works of art that adorn its walls and galleries,” the Tribune wrote. The judge determined that “the law had been violated to the extent of $100.”
Wooldridge didn’t pass any purity tests himself, however. In 1901, a state merit board found him guilty of “immoral conduct and conduct unbecoming an officer” and recommended that he be dismissed. The board accused him of taking money from one of the most notorious gambling bosses in Chicago, “Big Jim” O’Leary, to help get his first book published and forcing gamblers to buy his book and lithographic portraits of Chicago police superintendents, which he priced at a premium.
In many incidents involving Wooldridge, the police leadership looked the other way. But in 1901, Chief O’Neill had no choice but to fire Wooldridge. He wasn’t gone for long, however. Within months, he was back on duty, raiding matchmaking agencies. In 1905, a police board cleared Wooldridge after he was accused of abusing his police powers during a raid. O’Neill refused to issue a reprimand. “I have nothing to reprimand him for,” he said. “I shall keep on detailing him for the work which he has been doing, catching the swindlers and impostors.”
By 1907, though, the Police Department’s patience with Wooldridge had worn thin. The new superintendent, George M. Shippy, weighed reassigning him to a rural beat, either in Hegewisch or South Englewood, the Tribune reported, whichever “is determined ... as being the hardest to reach and the most difficult to get away from.”
The press also had grown skeptical of the detective. When Wooldridge set off to find the man who picked his pocket on a streetcar in 1912, the Tribune joked that the culprit would likely commit suicide if he knew of the former detective’s skills. “Clifton R. Wooldridge is the shrewdest, most indefatigable man that ever wore a detective star, the equal of (fictional detective Monsieur Lecoq) and far superior to the fictitious Sherlock Holmes,” the reporter wrote, then laid it on even thicker. “No man in the entire country is so feared by evildoers of all classes.”
His suspension in 1908 for allegedly leaking information to the defense in a murder trial set Wooldridge on the path to voluntary separation from the force. A police board acquitted him, but he resigned in 1910 to try his hand at acting and private investigation.
His home life was also a mess. In 1908, Wooldridge’s wife, Cora, filed for divorce, alleging he beat her so severely at times that she required medical attention. The suit came a few weeks after Wooldridge tried to commit their teen daughter to a reformatory. The court granted the divorce and awarded her alimony.
Neither setback tamed the detective’s hunger for attention. At his ex-wife’s boardinghouse, where he decided to stay after the divorce, Wooldridge pressed his books onto the other boarders. Cora Wooldridge called the police on him once for loudly reading from his books far into the night as retaliation for an argument.
At the same time as that run-in with the law, a local newspaper reporter came forward, claiming to have ghostwritten Wooldridge’s first book, “Hands Up! In the World of Crime, or 12 Years a Detective.”
“I used to go up there to give him readings,” the writer said anonymously, evidently still too embarrassed to disclose his name. “He would sit still and fascinated until I read some passage wherein he shone with particular brilliance. ‘Read that over,’ he would order. I spent more time reading that book than I did writing it.”
Chicago’s Sherlock Holmes died in poverty in the county hospital in 1933. Despite “numerous important assignments,” the Tribune recalled, his career as a detective “was a stormy one, complicated by his literary activities.” When Cora Wooldridge died in 1952, an obituary item identified her as the “widow” of Clifton Wooldridge, “city detective and author.”
The legend lives on.