John R. Livingston. If you were looking for a soundtrack for this post I would suggest \”Big Pimpin\”

John R. Livingston was an unrepentant businessman. During the Revolutionary War he had made quite a bit of money selling supplies to the continental army. Anything from gunpowder to rum. After the birth of the new nation John moved into a more tantalizing trade. As one historian put it John became the “Lord of Vice” in New York City. Another, less generous historian has called him a “whoremaster”.
John had cut his teeth as a merchant during the Revolutionary War. After a brief stint in the army during the Canadian campaign of 1775 he returned to his family’s land in 1776 to rebuild his father’s gun powder mill. He went on to buy and sell rum and other supplies for the army. John joined Benedict Arnold in a scheme to buy property from New York City loyalists which left him scrambling to prove his patriotism after Arnold turned his coat. He also bought up large quantities of depreciated Continental currency and encouraged his brother Robert R. Livingston to get Congress to buy it back for its full value.
To put it as simply as possible John R. Livingston was a businessman who placed profit above almost everything else once saying “Poverty is a curse I can’t bear.” So it should come as no surprise that when he saw an opportunity for profit in New York City after the war he jumped in with both feet.  
Edward Livingston mayor of NYC, brother of pimp
He began buying up property by 1802 and continued for years at every opportunity. He bought some of his brother Edward’s properties at auction when Edward fled the city following a scandal while he was mayor of the city. He later converted some of his older brother, Robert’s, city property into brothels after the Chancellor’s death in 1813. He even turned one property he bought from his mother, Margaret Beekman Livingston, into a den of iniquity. Most of John’s properties were on Thomas, Chapel, Anthony and Orange Streets making him the “most prolific entrepreneur of five points vice.” By the time John died in 1851 he owned at least 30 houses of ill repute. From a purely business perspective renting property to ladies of the night makes very good sense. There is little chance they would not have money on hand to make the rent, which is what John was mainly concerned with.

Five Points 1831

Some of the most famous courtesans of the day worked in John’s brothels including Abby Mead, Rosina Townsend, Mary Wall and Elizabeth Brown. Despite this John was still powerful enough that most people left his name out of condemnations of the trade. An 1836 publication described one of his houses as “so genteel in its exterior” but when on to say it was “one of the gateways to death and hell.” The houses, they claimed, were “knowingly let out for such purposes by one of our most respectable and pious citizens”, yet John was never mentioned by name.
Five Points in 1827, some of the women in this painting probably worked in John\’s houses
Only one time was John really called out for his activity. In 1830 a group of neighbors filed a complaint against some of his houses on Thomas Street. The complaint was not that the houses were being used as brothels but that the girls were displaying themselves in the windows of the houses nude. The complaint was against the madams who ran the houses but listed John as their “agent”.
John’s brothels also garnered the wrong type of attention in 1836 when a prostitute was found

The murder of Helen Jewett

murdered in her room. Helen Jewett had been struck in the head three times by a sharp object, most likely a hatchet, and set on fire. A suspect, Richard P. Robinson was quickly apprehended. During his trial most of the witnesses against him were other prostitutes. The Judge in the case ordered the jury to disregard their testimony. Robinson was soon found not guilty setting the dangerous precedent that it was fine to murder a hooker as long as you paid her first.

John R. Livingston lived in a golden time in American history when being associated with less than ethical business practices did not necessarily preclude a person from being a leading citizen. Despite having been known to have been involved in the prostitution trade in some form or another and being peripherally involved in several scandals John is remembered, when he is remembered, as a businessman and little more.
Sources and more information:
The Murder of Helen Jewett by Patricia Cline Cohen
City of Eros by Timothy J. Gilfoyle