Carrie Watson and Sig Cohen

After Annie Stewart's brush with the law, she retired from Madamhood and sold her interest in 441 S. Clark to Carrie Watson in 1868. In league with her boyfriend and financier, Sig Cohen, Watson upgraded the decor and quality of the women working within, and operated it as one of Chicago's finest brothels before and after the Fire, into the 1890s, during that time becoming one of the city's richest women. A businesswoman with an excellent eye for publicity, her house's supreme gimmick was a trained parrot who sat in a cage outside the door and constantly repeated, "Carrie Watson. Come in, gentlemen."

Sig Cohen's gambling operation, which provided the startup capital for Carrie Watson's business, operated at this location in the 120 block of S. Clark St., which at the time would have been 194 S. Clark. A sign above the casino read, "Diamond Broker -- Open Day and Evening".