Monday, September 1, 2008

Gentle Annie Stafford


"Gentle" Annie Stafford, the "fattest brother-keeper in Chicago," ran a brothel here at 155 N. Wells St., just north of Randolph, in the 1860s. Gentle Annie started her career as a prostitute in a house at the Sands in the 1850s, and was a notorious fighter, winning the affection of her madam when she led a battle against a rival madam who had recently stolen one of their best girls.

Later, Gentle Annie won the heart of Cap Hyman, the infamous gambler of Hairtrigger Block, who bought her this location, although she had to force him into marriage at the end of a bullwhip.

After the renumbering of houses in 1911, 155 N. Wells became 27 S. Wells. Currently, this location is a restaurant.

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