The area has high winds, lifting women's skirts up. Allegedly, an Officer Kane told some naughty boys to "twenty-three skidoo" from the scene. Scram! Beat it! Go away!
The problem here is that I've found articles about "twenty-three" in 1899. The Flatiron Building was completed in 1902. One theory is that "23" is the number of the last victim in the then-popular play version of Charles Dickens's novel A Tale of Two Cities, titled The Only Way.
"Skidoo" probably comes from "skedaddle," a term made popular during the Civil War.
I have several articles that credit the vaudeville actor Billy B. Van with combining the two slang terms into "twenty-three skidoo."
No doubt, the slang phrase was popular.
No doubt, it was used at 23rd Street.
Twenty-three skidoo the 23rd Street slang origin theory.
17 March 1899, The Morning Herald (KY), pg. 4:
DID THE SLANG PHRASE ORIGI-
NATE IN DICKENS' "TALE OF
For some time past there has been going the rounds of the men about town the slang phrase "Twenty-three." The meaning attached to it is to "move on," "get out," "goody-bye, glad you are gone," "your move" and so on. To the initiated it is used with effect in a jocular manner.
It has only a significance to local men and is not in vogue elsewhere. Such expressions often obtain a national use, as instanced by "rats!" "cheese it," etc., which were once in use throughout the length and breadth of the land.
Such phrases originated, no one can say when. It is ventured that this expression originated with Charles Dickens in the "Tale of two Cities." Though the significance is distorted from its first use, it may be traced. The phrase "Twenty-three" is in a sentence in the close of that powerful novel. Sidney Carton, the hero of the novel, goes to the guillotine in place of Charles Darnay, the husband of the woman he loves. The time is during the French Revolution, when prisoners were guillotined by the hundred. The prisoners are beheaded according to their number. Twenty-two has gone and Sidney Carton answers to -- Twenty-three. His career is ended and he passes from view.
22 October 1899, Washington Post, "How Slang Is Coined," pg. 19:
"By the way, I have come upon a new piece of slang within the past two months and it has puzzled me. I just heard it from a big newsboy who had a 'stand' on a corner. A small boy with several papers under his arm had edged up until he was trespassing on the territory of the other. When the big boy saw the small one he went at him in a threatening manner and said: 'Here! Here! Twenty-three! Twenty-three!' The small boy scowled and talked under his breath, but he moved away. A few days after that I saw a street beggar approach a well-dressed man, who might have been a bookmaker or horseman, and try for the unusual 'touch.' The man looked at the beggar in cold disgust and said: 'Aw, twenty-three!' I could see that the beggar didn't understand it any better than I did. I happened to meet a man who tries to 'keep up' on slang and I asked the meaning of 'Twenty-three!' He said it was a signal to clear out, run, get away. In his opinion it came from the English race tracks, twenty-three being the limit on the number of horses allowed to start in one race. I don't know that twenty-three is the limit. But his theory was that 'twenty-three' means that there was no longer any reason for waiting at the post. It was a signal to run, a synonym for the Bowery boy's 'On your way!' Another student of slang said the expression originated in New Orleans at the time an attempt was made to rescue a Mexican embezzler who had been arrested there and was to be taken back to his own country. Several of his friends planned to close in upon the officer and prisoner as they were passing in front of a business block which had a wide corridor running through to another block. They were to separate the officer from the prisoner and then, when one of them shouted 'Twenty-three,' the crowd was to scatter in all directions, and the prisoner was to run back through the corridor, on the chance that the officer would be too confused to follow the right man. The plan was tried and it failed, but 'twenty-three' came into local use as meaning 'Get away, quick!' and in time it spread to other cities. I don't vouch for either of these explanations. But I do know that 'twenty-three' is now a part of the slangy boy's vocabulary."
(From "Fables in Slang" author George Ade -- ed.)
WHERE DID "23"-THE MEANING OF WHICH IS GET OUTFIRST ORIGINATE?; There are a Lot of People Who Lay Claim to the Latest Slang Term of the Day. THE INTERPRETATION OF IT IS "SKIDDOO," OF COURSE But its Origin is Shrouded in Mystery, and it May be that "Police Gazette" Readers Can Throw Some Light on the Subject.
The National Police Gazette. Jul 7, 1906. Vol. VOLUME LXXXIX., Iss. No. 1508.; p. 6 (1 page)