Another guy about whom we have an insane amount of contemporary documents is the one and only Captain George Wellington Streeter - creator of Streeterville. As of the 1880s, Lake Michigan went all the way to Michigan Avenue. In much of the downtown area, everything east of Dearborn St. was still sand.
But then along came Cap Streeter. He had been sailing his houseboat around Lake Michigan, intending to sail to South America to become a gun runner, but, after crashing on the shore near the city, he hit on a different business plan: charging people money to dump their garbage around his boat. The massive landfill he created is still called Streeterville today.
But, being a bit of an eccentric, Streeter decided that the land was not only his property, but his own country, The District of Michigan, of which he was "lord emperor." Soon, it seemed that every bum in the city was emigrating to the "deestrickt," and a regular shanty town was set up, blocking the rich people's formerly unobstructed lake view.
This set of a thirty year battle between Streeter and the city that included both courtroom drama and actual gunfights. Streeter was one of the best known characters in the city.
In interviews with the guy that we've dug up, he sounds quite a bit like Popeye, only considerably more verbose - the city might be a very different place today if he'd ever gotten ahold of a can of spinach!
Having lost The Battle of Garbage Hill, Streeter died in the 1920s a disappointed man, still insisting that the district was his. Rumor has it that he cursed the whole district on his deathbed, but, given that Streeterville is now just about the fanciest part of the city, I have to imagine that if the curse story is true, he must have been TERRIBLE at cursing things. We do know that he passed ownership and the title of emperor on to the owner of the infamous Dil Pickle club, whose attempts to run people off the land and take possession of it lasted about five minutes.