War Veteran. Squatter. Captain. Gun-runner. Pioneer. Criminal. Land owner. Scoundrel. Liar. All of these words(and many others) could be used to describe George 'Cap' Streeter, an eccentric Chicagoan from the late 19th Century who inadvertently played a large part in helping create the Chicago we all know today.
According to his own self-aggrandizing legend, the whole thing started in 1886 when he ran his boat (named the Reutan) aground off the shore of Lake Michigan. Finding that the boat was impossible to extricate from he sandbar, Streeter just left it there. At this time, the Lake was still a popular dumping ground for all sorts of waste produced by the city(a practice that had started in the aftermath of the Great Chicago Fire). This, combined with the natural accumulation of silt, meant that eventually Streeter's boat was connected to the mainland of the city. By this time Streeter had organized the "United States District of Lake Michigan" around his wreck, refusing to recognize any outside authority, and inviting other squatters to join him. In 1889, he moved to another ship that had run aground in the dump, naming it the Castle. This touched off a period where Streeter and his fellow squatters would periodically fight off interlopers, be they dismayed wealthy land owners and industrialists in a court of law, or constables with gunfire and pots of boiling water(he beat the rap on the gunfire on account of the fact that buckshot wasn't considered to be a deadly weapon).
By 1892, the land that made up Streeter's squatter village was valued at approximately $300,000(which is equal to roughly $7.9 Million today). The following year, the District had accumulated quite the underworld element, attracting prostitutes, the homeless, and other 'undesirables'(somewhat reminiscent of another infamous red-light district). That same year, Streeter took advantage of the Colombian Exposition to make some more money. He re-floated the Reutan(the original boat he ran aground in 1886) and used it to ferry folks back and forth from his District to Jackson Park(the site of the fair). In the aftermath of the fair, there were many subsequent attempts to remove him, all of which were fought off either in the courts or in person. Streeter maintained his right to the District until his death in 1921(even though he moved to East Chicago 3 years earlier). Despite all the bad blood he'd had with the city through his life, the mayor of Chicago(who at that time was the infamous Big Bill Thompson) allegedly attended his funeral.
The actual facts of Streeter's life are a bit different. While he did serve in the Civil War, he wasn't a captain. He had acquired his boat in an attempt to take up a gun-running operation to Latin America. Coming upon the lakefront, he saw an opportunity to make a quick(and illegal)buck. He obtained permission from a landowner to dock his boat on the shoreline, and from there plotted to have the shoreline filled in so as to obfuscate the land titles, letting him "claim" land that was owned by(amongst others)the estate of William Ogden(Chicago's first mayor), Potter Palmer, and the Chicago Title and Trust Company. He then sold plots of land to other squatters, even going so far as to keep detailed records of collected property taxes. Eventually, Streeter claimed to own 186 acres of land right off of the lake. In reality, much of that landfill had actually been created for the building of Lake Shore Drive. To reassure skittish investors(as well as pressure landowners into paying him off) Streeter would periodically stage 'invasions' where he would lead a band of squatters onto his land with shanties. They would set up shop, the landowners would quickly send their goons after them, and then Streeter would complain that his rights were being infringed by the big, bad landowners. This process repeated itself until Streeter was convicted of manslaughter in 1902. After being sent to prison, Streeter eventually died at the age of 84 in 1921 from pneumonia.
While many of the facts of Streeter's life rest on the fence of him either being a folk hero or just a low-rent thug, what cannot be argued is his impact on the city. After all the squatters were evicted from Streeter's 'District', the developers moved in and started building. The building never stopped, and today the site of the John Hancock Center and the surrounding neighborhood is known as Streeterville.
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