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Even in the years before the Civil War, Chicago was a city known for its lawbreakers. During that time the most dangerous place to be was an area known as the Sands, a stretch of lake shore just north of the Chicago River approximately where the Tribune and Wrigley buildings now stand. In 1857, the area had about forty buildings, all of them gambling dens, saloons, and bordellos.

Now the most expensive bordello in the Sands was a house run by Anna Wilson, charging fifty cents a trick. Her most famous girl was a belligerent strumpet named Annie Stafford, but known to everyone as Gentle Annie. Annie was a renowned fighter and Anna Wilson’s main reliance in her war against Mother Herrick.

Most of the better whorehouses in the city were located on Wells Street, several blocks away from the Sands. (I find it fitting that one of the few adult bookstores in the city today is on Wells). Of these, the classiest was the Prairie Queen, run by Eleanor Herrick, better known as “Mother.” She was known to charge upwards of a dollar for the services of one of her girls. The Prairie Queen also featured erotic shows, dancing every night, and a bareknuckled prizefight for a purse of two dollars and a night with one of her harlots.

In early 1857, Mother Herrick lured away one of Anna Wilson’s best girls by offering her more money and a clean dress. Anna did not take kindly to this and for the next several days, prostitutes and their respective madames raged though downtown Chicago in a series of streetfights. The war remained a stalemate until the night of April 3, when Gentle Annie, with three more of Madame Wilson’s girls and several pimps rounded up from the Sands, made a surprise attack on the Prairie Queen. They broke down the door with clubs, smashed the furniture, chased away the customers, and administered beatings to Mother Herrick and many of her girls. Gentle Annie returned to the Sands in triumph, bringing back not only the stolen strumpet, but also the choice pickings from Mother Herrick’s flock.

Several years later, Gentle Annie opened up her own house of prostitution. She called her house the Sunnyside Hotel, and it was so popular that the street it was on is named Sunnyside Avenue today.

I love this town.

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