North of the Loop, between two of the famous tourist destinations of all Chicago, is a somewhat neglected neighborhood, and one of Chicago’s best if you ask those who live there.

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Streeterville has perhaps one of the city’s most colorful histories. The Chicago neighborhood is named after a con artist and petty merchant (who also dabbled in a ownership of a traveling circus, as well as Civil War soldiering) named George ‘Cap’ Streeter who moved to Chicago and promptly bought a small steamship with the intention of running guns to South America, but set his sights closer to home. Streeter ended up dumping his boat on part of the Chicago shoreline and leaving it there for years while he forged documents and made claims to state that the new shoreline he was creating around his ship was property outside of the city or states control, his own District of Lake Michigan. The intent, as stated by witnesses in his 1902 land fraud trial, was to extort millions from developers and lakeshore owners who would have to buy him off to get him to leave. Gradually expanding the land around his reportedly crashed ship, Streeter even went so far as to sell lots and collect property taxes on the freshly created lakefront. He would even send teams of squatters, once his organization was well underway and he was selling property far and wide that he had no right to, to set up overnight shanty towns and then defend them with tooth and nail, complaining to the city about thugs and capitalist plots against his homegrown property development. Numerous instances occurred where both private security and even police were injured or killed by gunfire, axes, and worse. However most of these cases ended with the con artist and his men declared not guilty—acting out of self-defense. (to be continued)

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