Nina Clifford, a child of immigrants who evolved into the “richest woman of the underworld,” made a name for herself as an affluent sex worker who contributed to the buildup of St. Paul’s downtown Red Light District in the late 1800s. She invited other women to establish their businesses nearby while police sanctioned an environment in which vice could thrive. In spite of a lack of preserved records, standing buildings, and extant photographs related to her business, Nina Clifford remains a legendary madam of St. Paul.