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Streeterville is a relatively small neighborhood located on the Near North Side of Chicago, Illinois. Its borders are between Lake Michigan and Michigan Avenue to the east and west, and Oak Street to Grand Avenue to the north and south. What Streeterville lacks in size, it certainly makes up for in money and property values. Easily some of the most expensive land in the United States, if not the world, in Streeterville you will find Chicago’s high-end shopping district, including the famous Water Tower complex, and the city’s most expensive hotels. Streeterville also holds Northwestern University’s law and medical schools and University of Chicago’s Graduate School of Business. Of course the most famous building in the area is the John Hancock Center, currently at least the 16th tallest building the world (depending on how you define “tallest”), and the tallest building that features residential units inside. A condo inside the Hancock is coveted by the city’s most rich and elite citizens.

What none of these people seem to know is the story behind Streeterville.

On July 10, 1886 George Wellington “Cap” Streeter and his common-law wife Maria were returning to Chicago from Milwaukee in their steamboat the Reutan, when they crashed into a sandbar just off the shore at the end of East Superior Street. Cap and his wife were taking the ship on a shakedown cruise in preparation for a trip south in order to make a fortune running guns for South American revolutions. Unable to dislodge his boat, Cap decided to make it his home. Cap and “Ma” (as Maria became known) encouraged the people that lived nearby to dump their trash in the area around the Reutan in order to increase their land. Slowly the trash in the water was covered with sediment and the ship was eventually connected to the mainland.

Noting an 1821 survey that declared that Michigan Avenue was the eastern boundary of Chicago, Cook County and the state of Illinois, Cap declared his land to be an independent republic named the “District of Lake Michigan” and named himself governor. Cap opened the District to anyone who wanted to move in, and soon the area was filled with transients, hobos, and prostitutes. In 1889, Cap and Ma moved into a larger ship which had run aground in the District and named it the Castle. Cap’s old ship was turned into a brothel. That same summer, prominent railroad financier N.K. Fairbank claimed that he had purchased the land that made up the District from the city and that Cap and the District citizens were illegal squatters. Cap chased off Fairbank with a shotgun.

This began a war between the citizens of the District and the city of Chicago. The city regularly sent policemen to evict the Streeters, but usually failed thanks to Cap’s shotgun, Ma’s pots of scalding hot water, and the loyal citizens of the district. Even when the police managed to kick them out, they were never gone for long. After one such raid resulted in Caps arrest for assault with a deadly weapon, he was acquitted on the grounds that buckshot was not considered deadly. In many other cases where police were injured by axes and gunfire, Streeter and his men were invariably found not guilty due to acting in self-defense. In 1893, Cap was able to refloat the Reutan and used it to ferry citizens of the District back and forth to the fairground of the World's Columbian Exposition, located on the South Side of the city in Jackson Park.

Fairbank continued to win court battles against Cap, but the city was never able to clear out the area. The fight continued for decades, until finally in 1918 the police forcibly removed everyone from the District and burned down the Castle. Cap and Ma Streeter moved to East Chicago, Indiana, where Cap died in 1921 of pneumonia.

The multimillion-dollar condos of the John Hancock building now sit on the exact spot where Cap Streeter’s steamboat brothel once rested.

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