In the 1820s, it was an open-air market for horses and dry goods bordering a genteel neighborhood of row houses (as seen here, in an illustration looking back on 1812).

By the 1850s, Chatham Square was kind of the Times Square of its day, a seedy district of flophouses, taverns, cheap merchants, and the city’s first tattoo parlors on the outskirts of the East Side’s notorious Five Points slum.
How seedy was it? Describing the prostitution rampant there in his book City of Eros, Timothy J. Gilfoyle writes:
“Along its western edge, the Bowery and Chatham Square were a bourse of sex. The patrician George Templeton Strong claimed that after nightfall, amid the theaters, saloons, dance halls, and cheap lodging houses, the thoroughfare overflowed with ‘members of the whorearchy in most slatternly deshabille.’
“Once elegant eighteenth-century residences like that of the merchant Edward Mooney at 18 Bowery now served as brothels.”
Like everything in New York, the red-light districts change as well. Prohibition, the Depression, a growing Chinatown, and slum clearance all remade Chatham Square into a messy but not sleazy intersection off the Bowery.

It’s now known as Kimlau Square, which honors American servicemen of Chinese ancestry who died for their country.
[Above photo: an 1853 Daguerreotype of Chatham Street, now Park Row, looking toward the Square]