A classic con trick, he made at least $500,000 using this swindle during a five-month period at the Columbian Exposition of 1893[4][5] as one of many figures of the criminal underworld who attended the event.
[6] A native of Chicago, Illinois, Tom O'Brien first appeared during the early 1880s, becoming notorious for his con games and confidence tricks.
Grey, a highly popular courtesan and madam in the city's underworld, ran a high-class "bagnio" on Burgundy Street and was extensively involved in confidence tricks in New York, Atlanta and Paris before arriving in Louisiana.
[9]O'Brien was able to take a Michigan farmer for $21,000 using this ploy, perhaps his most successful effort, but was eventually arrested for the 1889 theft of $10,000 in bonds from Albany businessman Rufus W. Peck in December 1891.
[11] On April 21, 1892, O'Brien escaped from custody in Utica, New York while being escorted by James B. Buck on a writ of habeas corpus.
[4][5][6] He eventually fled to New Orleans, possibly after a tip to his whereabouts by a South Side Chicago saloon keeper,[1] and then to Paris, where he stayed briefly until an incident with a gendarme nearly caused his capture.
In March 1894, an anonymous letter was received in Little Falls, New York in which the author, claiming to be a close friend of O'Brien, disclosed the whereabouts of the fugitive.
It was reported that O'Brien was serving as a soldier in Haiti, having fought in defense of the government during the insurrection, and that he was considering entering politics given his recent popularity.
[12] O'Brien eventually returned to Paris in late 1894 or early 1895 where he and Reed Waddell, another con man he previously worked with throughout the U.S., became partners in a banco swindle.
The New York City Police Department believed otherwise, Detective Sergeant George McClusky publicly stating there was "little doubt that the man under arrest was Tom O'Brien", and American authorities petitioned the French government for his extradition.
His defense attorney Maftre Demange had claimed during the trial that the two men had exchanged gunfire, rather than O'Brien having killed Waddell in cold blood, and that gunfights were common in settling disputes in the United States.
He also downplayed O'Brien's criminal record, claiming he was "merely a gambling cheat", and that he was in fear of his life and acting in self-defense at the time of the murder.