Oakey Jackson, “Larceny by Trick”, 22 September 1959

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Oakey Jackson

A sixty-five-year-old woman named Margaret Ashby was standing near the cab stand on Washington street one afternoon when a young woman she had never met before struck up a conversation with her. After they had spoken for a while—the woman was excited about the money she stood to get from a new job in Pittsburgh and Margaret had somehow found herself talking about how much money she had saved up—they noticed a man picking up a wallet from the sidewalk. The man—Oakey Jackson—stopped and showed the wallet to the women. It contained a bundle of large bills, along with bookie slips and gambling receipts. Oakey was well dressed, neat and polite. He spoke eloquently but quickly. Clearly, the wallet belonged to a criminal, so there was no point giving it to the police, as nobody would go to collect it. Oakey said he would give the women $80 each if they told no one that he had found it. First, though, he had to go to a bank to ask his boss’s advice. His boss was fond of him, as he had saved his son from drowning.

While Oakey was gone, the woman kept telling Margaret how lucky they were to have happened to meet the man. When Oakey returned, he said his boss had said they should keep the money and split it three ways, but that he should make sure that the women were reliable, respectable people who would use the money wisely by getting them to put up some money of their own, to show good faith. The young woman said that was fine by her, and handed over $90. Margaret was about to volunteer to get her savings from the bank when Oakey was arrested by a police officer who had been watching the group since Oakey had approached the women.

Oakey turned out to be an infamous underworld figure, known from Ohio to New York as the flim-flam king; the young woman his accomplice. Oakey’s record stretched back to 1921, with arrests every few years since for picking pockets, petty larceny, grand larceny, larceny by trickery, swindling, robbery, carrying a concealed weapon, escaping from prison and driving while under the influence of alcohol. He had spent only five years in jail, paying fines instead of serving time. In 1951, his testimony that he had paid a quarter of his illegal earnings to the police in Cleveland in return for protection sent two officers to jail for six years. He was notorious enough to be summoned to appear before a Senate subcommittee on delinquency to explain how young people get into the flim-flam trade, and he was successful enough to be able to buy a twenty-room hotel in Cleveland, in which, people said, he ran a school for confidence men.

The New Castle police let him go. He had been arrested before a crime had been committed.

The following year, the police in Boonville, Missouri, filed charges against him for swindling $3,050 from a plumber. He was not apprehended. There is no further record of Oakey’s criminal activities. In 1965, at the age of sixty-one, he appeared in the news for the last time when he was abducted at knifepoint and forced to drive to a deserted parking lot where his hands were tied behind his back with his necktie and he was robbed of $281.

Oakey died in Cleveland in 1977, at the age of seventy-three.

Sources: New Castle News ( 23 September 1959, “2 From Cleveland Face Charges Here”; 26 September 1974, “Death Record”); Baltimore African-American (1 December 1951, “Swindlers Talk; Tell Of Bribing Cops To Operate”; 24 November 1956, “”Oakey Jackson Arrested Again”; 18 December 1956, “Oakie Jackson, Who Blew Whistle On Local Cops, On Trial In PA”; 25 November 1964, “How ‘White Collar’ Criminals Operate Here”); Cleveland Plain Dealer (27 September 1965, “Man Abducted At Knifepoint, Robbed of $281”; 13 April 1977, “Death Notices”); “Juvenile delinquency: exploitation of minors in interstate confidence racket. Hearings before the Subcommittee to Investigate Juvenile Delinquency of the Committee on the Judiciary, United States Senate, Eighty-fourth Congress, second session. December 11, 12, and 17, 1956”.


    • Yes, it seems to have been. Thanks for the link. I admit, I’m still pretty baffled by the process. Oakey’s approach seems to have involved confusing the mark with a lot of misdirection, fast talking and inclusion of odd details like the bit about the son being saved from drowning.

      I found a clip of a film called The Flim-Flam Man (1967), which shows Slim Pickens falling for a pigeon drop. It’s a slightly different set-up, but more or less the same…

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