Chicago's Last Pioneer

Published July 27, 2021
Chicago's Last Pioneer

The Eccentric Life & Death of Cap Streeter

On this day, January 22, 1921, one of Chicago’s most unusual, eccentric and entertaining characters breathed his last. Captain George Wellington Streeter was considered by many to have been the last Chicago pioneer. Whether he deserves this title or not is another question, but he was certainly a colorful character and one that remains surrounded by lore that is uniquely a part of Chicago. During his years in the city, he defied the laws of Chicago and the state of Illinois, fought the courts and the police to a standstill and managed to keep the residents of the region in alternating states of anger and amusement for more than 30 years.

Streeter's greatest Chicago legacy was created by nature rather than by man. The waves had been beating unchallenged against the shoreline of Lake Michigan for centuries before the settlers came to Chicago. Along the open area north of the river, the lake deposited generation after generation of silt and sand and as it did so, the shore crept ever eastward. On the west side of what was known as Sand Street in those days, the city’s wealthiest residents claimed rights all of the way to the water’s edge, no matter where it might end up. As the beaches grew larger, so did their parcels of property. There was never any dispute about this until one summer day in 1886 when a strange and eccentric character laid claim to the vast Chicago shoreline – and made plans to hold that land with his own personal army!

 Captain George Wellington “Cap” Streeter, one of most colorful characters in Chicago history.

George Wellington Streeter was the great-grandson of an American Revolution veteran and the grandson of a drum major from the War of 1812. He was an avid showman and before he arrived in Chicago, he had roamed the West, had served in the Civil War (seeing action at Missionary Ridge and Lookout Mountain), had watched his first wife run off to become a vaudeville star, had worked as a freight hauler, had been a hotel owner and for a time, was a business associate of two unsavory brothers from Missouri named Frank and Jesse James. Or at least those are the legends he told…

After his service in the war, Streeter brought together a menagerie composed of animals no more exciting than deer, otter, porcupines, and beavers, but he still managed to exhibit them at county fairs with some success. His prize exhibit was a white Normandy hog, which he insisted was 10 feet long and weighed over 1,500 pounds. He usually billed the beast as a "white elephant," to the delight of the crowds who came to see it.

Streeter's dubious business prospered for a while but when ticket sales slumped, he traded in his animals and became a ship navigator on the waters of Lake Michigan and the nearby rivers. He landed in Chicago in the 1870s and became part owner of the Wood's Museum, a famous showplace of the time. He soon sold out and became a salesman at county fairs, then left that business and served as a short-term owner of the Apollo Theater.

Bored in the city, Streeter returned to the lake, lured by the hope of striking it rich in Honduras. His second wife, Maria, was a raging drunk and would often disappear for a week at a time on a bender. Cap Streeter, as he was often called, never worried about her when she went missing. "It don't matter where she is," he would often say. "She's having a good time and will come home when she's ready." During one of her disappearances, Maria made a friend, a Captain Bowen, who convinced her that there was money to be made in Honduras. There was a revolution taking place there at the time and all a seaman had to do was to arrive in the country with a boatload of guns and he would find himself with a steamship concession on the rivers of Honduras.

Cap Streeter at work on the Reutan.

Soon after, Streeter began to borrow money and to build his own steamship, which he called the Reutan. He wanted to test her for seaworthiness and decided the best place to do so was on Lake Michigan. Streeter, Maria, an engineer and four passengers set out on July 10, 1886. A sudden storm blew in off the lake and the steamboat was nearly lost. They managed to make it to a point near the Chicago harbor, missed the breakwater, drifted northward and finally washed up onto a sandbar along the beach. Streeter had lashed himself to the wheel to keep from being washed overboard in the storm. Despite the grounding of his boat, he was not defeated. In fact, he took a look around and decided that the spot where the boat had washed ashore would make a fine place to live.

The boat remained at the site throughout the fall and into the winter. A sandbar began to grow up around it and Streeter offered local contractors the privilege of dumping sand, dirt, garbage or anything else they wanted near his new home. The lake continued to contribute sand as well and soon, the boat was no longer in the water but resting on dry land. In this way, Cap Streeter "created" 186 acres of his very own land. He had managed to find an older map of Chicago that indicated that the shoreline was actually west of his property and now claimed that he was beyond the shore of Chicago and Illinois. He dubbed this new property the "District of Lake Michigan" and while he recognized the laws of America, he declared that he was subject to no other rules or regulations.

The local property owners, the most noted of whom were Potter Palmer and N.K. Fairbanks, made it their common cause to get Streeter removed from the land along the lake. In their eyes, he was nothing more than a crude, obnoxious squatter and a blasphemous, drunken thief who had to be ousted. Streeter was throwing loud parties for other riff-raff in the region and worse, was selling liquor on Sunday. This was against the law in Chicago, but Cap had decided that it was perfectly legal in his district. Palmer and Fairbanks soon learned that threats did not work with Streeter, so they began to pursue legal options. Had they gone to the civil courts at once, things might have turned out differently but they went to the police instead, which started a guerilla struggle that lasted for years. The battle involved the city police, the park police, special constables and dozens of lawyers. The courts were appealed to over and over again and Cap was arrested several times but always managed to go free.

A houseboat that had been turned into a house in the new district of Streeterville 

Eventually, the Chicago gentry, with their now-obstructed view of the lake, thanks to Cap's boat, outhouses and ramshackle buildings, chose less subtle methods of moving Streeter off his land. In the summer of 1894, five men from Chicago Title and Trust served Cap with orders to remove himself from the property. They received shotgun pellets in their backsides for their trouble. When three policemen came to arrest Cap for the shooting, Maria doused them with boiling water, forcing them to retreat. Cap was later arrested but no charges were pressed because there was still a dispute as to whether Streeter owned the property and whether or not the men were trespassing.

Later that fall, Cap's house was attacked by 25 police officers, working on an unofficial payroll from Potter Palmer and his compatriots. Streeter opened fire on the men and Maria managed to nearly sever the arm of one of them. After they were arrested, all charges against them were dismissed after they claimed "self-defense." Around this same time, Cap discovered the old Chicago map that indicated that his district was outside of the city limits. He named William H. Niles as his military governor and set about creating a separate state from Illinois. In 1899, he turned one of the outhouses on his property into a courthouse, raised an American flag and issued his own "declaration of independence." Streeter and a number of his friends were arrested on charges of illegal assembly but were later released.

On May 25, 1899 (just a few weeks after Streeter declared his district independent of Chicago and Illinois), more than 500 handpicked police officers charged into Streeter's district because Cap allegedly shot at a police captain's carriage. Military governor Niles had already entrenched Cap's men around the property and he armed his troops with a cannon that had been stolen from a nearby park. The city soon had Streeter's district surrounded with officers in the front and a tugboat that was armed with a Gatling gun in the rear. The police charged but were repulsed by buckshot and rocks. Around nightfall, the police officers charged again and managed to overwhelm the ragtail "army." Streeter was captured but was soon released and the police officers involved in the fiasco were reprimanded for their roles in the affair. In those days, it was not illegal to shoot at a police captain's carriage.

But no one was willing to let the matter go away quietly. One night while Streeter and his wife were out of the house, several officers broke into their house and confiscated a number of Cap's guns. Enraged, Streeter marched down to the Chicago Avenue police station and took all of the officers and staff hostage. He demanded the return of his guns and when they were given back, he left the station peaceably. Cap was soon arrested and charges were filed against him. His defense turned out to be so eloquent that he was acquitted.

One of the shacks located in the “District of Streeterville”

Another bizarre incident occurred in the spring of 1900. A group of men, posing as land buyers (Cap had been selling off lots of real estate from an office in the Tremont Hotel) took over the district while Streeter was away and burned down his house. Cap quickly responded and after raising an army, marched into the District and took back the property. Police officers were again raised in response. Three-inch guns were mounted onto two of the city's fire tugs, 16 patrol wagons were lined up outside of the district and over 400 officers were called in to serve as troops. The volatile standoff ended when a lone policeman convinced Streeter that he should surrender himself. He did so and was acquitted again of all charges against him.

In 1902, Streeter and several of his cronies were indicted for forging the name of President Grover Cleveland on a land grant that "proved" that his district was outside of the jurisdiction of Chicago. It was later reported that the document Streeter used was actually a paper signed by President Martin Van Buren that gave certain lands to John Kinzie and his heirs. The heirs then immediately sued to have the land returned to them, which meant that the wealthy citizens who were trying to get rid of Cap Streeter for being a squatter were now being accused of being squatters themselves. The case eventually went away and Palmer and the others were able to again focus their attentions on the Streeter persoalan.

Cap Streeter - holding the dog - and some of his supporters and residents of Streeterville. Note the man to the right of Streeter holding a rifle to his shoulder

And it was in this same year that things took another turn and for the first time, Streeter actually ended up in jail over the matter - only this time for something that he didn't do. Wealthy business owners and their cronies hired a gunman from Missouri named John Kirk to go in and clear Cap out, no matter what it took. Days later, Kirk's body was discovered in a Chicago alleyway, riddled with bullet holes. Streeter was shortly arrested and railroaded through the courts with a guilty charge for murder. He was sent to Joliet prison and while he was there, Maria died from exposure and hunger. Streeter cursed Chicago for her death. He was eventually cleared of the charge, and released with a full and unconditional pardon, but he was never the same again.

In 1906, he re-married, though, this time to Alma Lockwood, who was 33 years his ingusan. Streeter had managed to hang on to his district, now dubbed Streeterville, for years but his days were numbered. By 1915, the land actually controlled by Cap had dwindled to nothing more than a fenced enclosure that surrounded the remains of his home. Streeter still held parties there, though, and sold liquor, even on Sundays, which was still illegal. The city informed him that he had to obtain a liquor license and sent several police officers to enforce the order. Streeter stabbed the sergeant who carried the papers in the behind with a bayonet as a reply. He was arrested but was quickly bailed out.

Cap married Alma Lockwood in 1906. She was 33 years younger than he was, but she stood by him for the rest of his life.

The following day, eight policemen charged into the district and attempted to arrest Cap again. Two of them grabbed Alma's ax but she managed to disarm six of the officers anyway. Another officer was wounded by birdshot from one of Cap's guns. Alma was arrested after the incident for "assault with intent to kill" but she was acquitted when it came out in court that none of the policemen ever identified themselves as officers.

After years of defending himself against attackers, the city of Chicago and the court system, Cap Streeter was finally defeated on December 11, 1918. On that day, the courts finally decided that Streeter had no real claim to the land that he called Streeterville. He was finally evicted and his home was burned to the ground, marking an end to one of the city's most unusual eras.

Streeter remained an eccentric Chicago character until the day he died. He began selling hot dogs and coffee at Navy Pier and lived comfortably in a new houseboat that he had purchased called the Vamoose. His tamat days came after he lost an eye while chopping wood. A sliver of kindling flew upward and put out his eye, which led to an infection. He contracted pneumonia in his weakened state and died on January 22, 1921 at the age of 84. The mayor, and half of the city, attended his funeral.

The Vamoose became a menace to navigation and was destroyed by city order in 1928. Alma, who saved only Cap's musket as a memento of their life together, ended her days making and selling aprons and she died in 1936. She never gave up on her husband's claims to the ownership of Streeterville, though, and she and his heirs continued their lawsuits until 1940, when a federal court finally dismissed the claims.

Oddly, this is not quite the end of the story… The original Streeterville District extended from the Chicago River to Oak Street Beach, east of Michigan Avenue. Cap's claims to this area were little more than a nuisance to the wealthy and privileged in his day but now, the land would be worth billions. Today, old Cap Streeter is barely remembered by most, except for the name Streeterville, which still persists in Chicago. For this reason, it would likely come as a surprise to many to learn that the presence of Streeter still lingers today -- in the form of a curse that allegedly "haunts" this part of the city.

Legend has it that Cap Streeter's final words were a curse on the politicians and on the city of Chicago for the real and imagined wrongs that had plagued the last several decades of his life. This story was often told, but nothing much was thought of it until the 1970s. Just a few years before, Streeterville had been changed forever by the construction of the massive John Hancock building. Erected between 1965 and 1969, the giant structure loomed high over the city around it. Despite the stories, though, no one died during the dangerous work that was done to create the building. However, that quickly changed after the tenants began moving in. A series of strange deaths began to plague the building, including the murder of a man on the sixth floor and a number of unusual fires.

The strangest, and most widely reported death, occurred during the early morning hours of August 12, 1971. The victim was one Lorraine Kowalski, the girlfriend of affluent Marshall Berlin, vice president of I.S. Berlin Press, a Chicago printing company. The two of them spent the evening of August 11 separately, with Berlin out for dinner with another woman and Kowalski visiting nightclubs on the near north side with her friend, Carol Thompson. Kowalski reportedly returned to the Hancock Building at about 3:30 a.m. on the morning of August 12. She was incoherent, alone and exhausted from her night out. According to reports from residents, Kowalski and Berlin became involved in a volatile argument, but Berlin told investigators that Lorraine had simply been despondent over the direction their relationship had taken. Thompson told police that her friend had been intoxicated well before midnight.

In the midst of the argument, Berlin retreated into the bathroom. When he came back out a few minutes later, he stated that the bedroom window had been shattered and that Lorraine's clothing was scattered about the room. It was 4:10 a.m. and Berlin placed a quick call to the Chicago Avenue police station. 
Apparently, while he was in the bathroom, a naked Kowalski plunged out the window of the apartment and fell to the pavement many floors below. As she fell to the street, she took numerous shards of the window glass with her -- which remains one of the most puzzling parts to this mysterious incident. The double pane of glass in the apartment window was capable of withstanding 280 pounds of pressure per square foot and yet somehow, the slight 130-pound woman managed to break through it.

Berlin refused to take a polygraph test and told the investigators that Kowalski had threatened to commit suicide just moments before he went into the bathroom. No charges were ever brought in the case and it remains unsolved to this day.

This death joined numerous others that occurred in the area. Was it merely a coincidence? Or is the area shadowed by Cap Streeter's legendary curse?

Streeterville is just one of the many places visited on the Weird Chicago Tours, the best ghost tour in the Windy City! Check out upcoming tours and events by going to the Weird Chicago situs web and we’ll see you on a future tour!


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