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According to historian Judith Kellehar Schafer, the majority of prostitutes in and around the area were immigrant women. Prostitution, known as New Orleans' second most profitable industry, The second most profitable industry in New Orleans, prostitution, also benefitted from the transient guests of Gallatin Street.
Schafer cites a study published by William W. Sanger in on the sex industry. Sanger found that after women were entangled in sex work, they often died within four years. He also found that at least fifty percent of prostitutes had sexually transmitted diseases. Such violent acts were not uncommon on Gallatin Street. While women were often victims of violent crime, some women were also active criminals.
Another famous woman, Mary Jane Jackson, better known as Bricktop, skipped theft and went straight to assault. A scourge throughout New Orleans, Bricktop also worked for Archy Murphy until she was deemed too rough for even one of the roughest dance houses on Gallatin Street. It is said that she carried a knife personally designed with two five-inch blades on either end. In December , she took her violent streak so far as to kill her own husband.
The Times-Picayune commented on the murder as such: In , Swan successfully led a brawl of men and women against the police, then assaulted a man and beat a woman in two separate instances. The bar owners had to be tough to run a club on this street, whose drunk and rowdy clientele could often hold their own in a fight and had very little to lose. Although a motley crew, they were the closest thing to organized crime in the area.
Herbert Asbury claims that the group earned their name by carrying around oak clubs, and because of their meeting place near the river in a pile of live oak knees. They were generally unwelcome in brothels because they were sure to cause a fight. Asbury claims that Bill Swan was once a member of the Live Oak Gang, but after Swan made a good amount of money, he invested in business rather than crime.