The Cap: The Life and Times of Chicago’s Real-Life Folk Antihero

It was a dark and stormy night in 1886 Chicago. In the new, unknown city, children were tucked away in their beds, covering their ears and eyes as each racking set of thunder and blinding strike of lightning kept them from their sweet dreams. The tempest swirled over Lake Michigan where no captain dared set sail. No captain, except for one.

Captain George Wellington Streeter knew no fear. A Civil War hero, pioneer of the great Midwest, lumberjack, and friend to beasts big and small, he stood firmly at the helm of his vessel, howling back at the storm. With his arms spread wide as the albatross, the sleeves of his waistcoat flapped defiantly in the wind. He was set in his course, dead-aimed for the shores of the new horizon that was Chicago. There wasn’t a storm strong enough to hold him back. Though, this one sure tried.

Thunder rumbled so fiercely it made the seas quake, in the hopes of flushing out Streeter and his ship. On its maiden voyage, the boat moaned under the weight of the storm, gargling each wave and spitting it back into the vast liquid chaos. The captain’s red hair flared like flames and his deep blue eyes dashed wildly across the raging waters, squinting deeply to locate anything amid the opaque sheets of rain. To the north, it poured down with the thickness of a waterfall; to the east, it blew in sideways. In the west, it swirled in threatening circles, lost in the insanity of its own fury. There was no looking back.

Streeter’s wife, Maria, braced herself in the cabin of the boat, armed with the fierce loyalty and blind trust she held for her husband. “George!” she screamed to him. “George! The shore!”

Smack! Splash! Creak! Crash! A final shriek from Maria … and then silence.

When morning came, the clouds parted high above the calmed sea. Streeter emerged to the bow from the mist, snapped his suit jacket, and straightened his silk top hat as he presided over the promised land. Birds sang from the shorelines welcoming the captain to his destined home.

Streeter crashed just four hundred feet from Chicago’s Superior Street. His battle with the storm was won and his prize was the sandbar upon which he landed. He christened it “The Deestrick of Lake Michigan,” spelled just the way he said it. And while it was not land fit to be claimed, let alone built atop, expanded upon, and sold off, Streeter did just that. He’d live there, and make his living off of it, for the next thirty-five years.

“The deestrick is mine” he told a Tribune reporter in 1901. “I discovered the deestrick. Who was the first man to know there was any land up there? Capting Streeter. Who was th’ furst man to live thar? Capting Streeter.”

The city had a different opinion: Streeter was squatting. But as they fought it out in the courts, Streeter lived on the ever-expanding shantytown on the lake until his death in 1921. During that time, his legend only grew, as he basked on the shore of Chicago’s primest of locations, and the modest profits that came with it.

Streeter’s story has a folk-lorian quality. Despite a three-hundred-plus-page biography of his life, court records, and accounts in the news and history books, it’s hard to tell what was true and what Streeter wanted us to believe. He boasted. He lied. Then, he boasted about his lies. He made criminal-level claims before a judge without flinching. Even his origin story of coming to Chicago doesn’t shake out. Weather Bureau records indicate there was no storm the night Streeter crashed into Chicago.

Unbelievable in modern context, Streeter’s legacy remains. The Civil War veteran from Michigan, who by no record was ever ranked captain, earned himself a namesake neighborhood. In the nineteen sixties, the Near North Side area closest to the district was dubbed Streeterville. Today, it’s home to lavish condos, hotels, and restaurants, Navy Pier, and Ohio Street Beach. It embodies the lifestyle Streeter dreamed to achieve but never seriously approached.

A Civil War veteran, Cap (center), with Spot, shares some stories with the Second Illinois Field Artillery camp at East Chicago Avenue and Lake Michigan. (Photo Courtesy of Chicago History Museum)

Streeter was forty-nine years old when he shipwrecked on our shores, but it wasn’t his first time in the city. In his twenties, Streeter traveled the Midwest for a place to stake his claim. Much like his father (William Streeter, the seventh settler of Flint, Michigan), Streeter thought himself a pioneer. He wasn’t even impressed with Chicago at first. It was too small. He preferred Kankakee and what’s now south-suburban Wilmington.

To Chicagoans, Streeter’s crash-landing seemed pedestrian at first. He asked permission from the nearby landowners if he could leave his ship there while he repaired it. He was the guy “just crashing on the couch for a while.” As the years went by, it became clear he wasn’t leaving anytime soon. Self-proclaimed governor of his newly created district, Streeter began selling parcels of surrounding land to developers looking to dump debris. With his wife, Maria, by his side, Streeter erected a two-story home to replace his boat, and they lived on the second floor. On the first floor was their “war room,” containing an artillery of weapons they would use to defend their homestead.

Known as Cap to all, he was short in stature. He wasn’t handsome, but those who looked into his blue eyes were called to pay attention. His red hair, bristly oversized mustache, and long manicured beard accented a face you did not forget. He often wore a three-piece suit, a tie underneath his battered top coat, and a pocket watch dangling across his vest. His dress was typical of middle-class fashion of the time but his bushy eyebrows, weathered complexion, and sloppy, choppy speech communicated: This was a man of the people. He carried around a yappy dog, Spot, for good measure. By many, Cap was revered as a champion of the commoner, someone who was standing up to The Man by staying put on the district. It was in these circles that his legacy evolved into mythical legend. The association served him well. To defend the land, Cap needed people. His oratory skills, confidence, and sense of entitlement earned him a gun-strapped militia.

By many, Cap was revered as a champion of the commoner, someone standing up to The Man by staying put in the district.

Having served in the Civil War, Cap said living on the land was his “right to homestead,” a law that allowed Americans to claim federal land at no cost following the war. In other occasions, he claimed John Scott, who lived in an undisclosed location in Michigan, sold him the land. In 1902, at a show at the Metropolitan Theater on Clark Street, Cap took his story from the dramatic stage and said he bought one hundred acres from Chief Pokagon. When the court tried evicting Cap from the district, he was done with empty claims. He produced a grant from President Grover Cleveland that stated the property was rightfully his. He stood by the grant for twenty-five years until finally a handwriting expert took a closer look. The Tribune reported, “Lo and behold, the signature of Cleveland faded away, and there arose in its place the quaint and sturdy signature of President Martin Van Buren!” Streeter’s name also vanished from the grant, revealing the rightful owner to be Chicago’s Robert Kinzie. The judge ruled that the document “was and is now a clumsy forgery.”

Cap’s Early Life
In the biography “Captain Streeter, Pioneer,” written in the early nineteen hundreds, author Everett Guy Ballard brings to light a different side of Streeter than we see in newspapers and court documents. It’s written in the first person as if Cap is speaking, but it’s clearly Ballard’s voice. Wherein the Tribune Streeter is quoted in a broken fashion, the biography reads eloquently. Several of the chapters sound like philosophy text, touching on the immorality of slavery and the vast wilderness of an untouched America. Ballard provides a strong biographical profile nonetheless. He tells us Cap was one of eleven children born in Flint, Michigan, in 1837. His childhood is filled with stories of the happy hunting of pheasants, wolves, bears, and everything in between. Other times tell of making maple syrup with his siblings on the sugar camp. The children tamed fawns, wildcats, and raccoons trapped by their father and turned them into pets.

At eighteen, Streeter became a logger and then got into boat-building. During this time, he met and engaged Minnie Waters in a marriage that would dissolve in 1869 when she would take Streeter’s money and run off to perform in a Vaudeville act. She would be his first of four wives.

Due to his position against slavery, Cap volunteered to serve in the Civil War, but his captain title was self-appointed, not a military designation. Following the war, he returned to Michigan and purchased five thousand dollars worth of animals with dreams of operating a traveling menagerie show. In the mix was a fifteen-hundred-pound white hog that he billed as a white elephant. No one seemed to mind, though, Cap tells Ballard.

When the show failed to make a profit, he sold it off in Indianapolis and took a dive into the hotel business. That failed, too. Here in the timeline, Cap comes to Chicago to operate the Woods Museum, the Chicago equivalent to P.T. Barnum’s New York museum of oddities. But he dropped that as well. Back to boat-building he went, which led him directly to Chicago’s shore.

Cap and third wife, Maria, shipwrecked into Chicago on the Reutan, which they docked and lived aboard. (Photo Courtesy of Chicago History Museum)

The Development of the District
When the boat crashed against the sandbar, Cap says he landed right where he meant to. By his account, he was using the boat to carry passengers from Milwaukee to Chicago but said they abandoned the trip after hearing of “the storm.” We learn through other accounts that the original idea for the boat was to run guns to Honduras, which is why the boat was named Reutan, a misspelling of the Honduran island Roatan.

At the time of the crash, everything east of Michigan Avenue was swampy. Lake Shore Drive had yet been built, but contractors were swarming, and Cap saw opportunity. Since the area wasn’t connected to the state’s land, and the land underwater wasn’t claimed by the state, city, or county, Cap had successfully wiggled his way through a loophole. He told those who allowed him to stay temporarily that he’d be there permanently, and the land was rightfully his. To make additional income, Cap sold portions of the land to two hundred people. For tourists and curious visitors who stopped by, concessions, including alcoholic beverages, were sold. It was a manipulated version of the menagerie and oddities museum he’d previously operated, but this time, he peddled anarchy and freedom, and this time, it stuck.

Violence in the District
During his thirty years defending the district, Cap was no stranger to the law. In one case, five hundred policemen surrounded the district, and Cap and his fellow squatters met them with gunfire. Crist Mantis, who opened a popcorn stand on the district, was punched in the jaw by “Patrolman Sullivan” according to a 1915 Tribune report. Nonie Hollst, who lived on a wagon in the district, was shot in the hip by another officer. In another instance, it was the police who endured violence: One officer was doused with scalding water as he tried to arrest Cap.

In 1902, Cap was arraigned on a more serious charge than squatting or brawling: the murder of a known hired killer, John Kirk. It was rumored the Kirk had been sent to kill Cap, but Cap acted faster. At first, this wasn’t a battle Cap could win. He was found guilty of manslaughter and sentenced to life in prison. He served several months in the Joliet Penitentiary in the winter of 1903 and was then freed on the basis of habeas corpus (unlawful imprisonment). Cap never gave up the argument that he was framed, and the governor of Illinois at the time, Richard Yates, Jr., believed him.

With Cap’s good luck came some bad: His wife, Maria, had died while he was in jail.

Ma, Cap, and Spot lived together in a two-floor shanty on the shoreline. (Photo Courtesy of Chicago History Museum)

Cap and Ma
Cap made heartbroken statements about Maria’s death and the unjust circumstances under which it happened. But three years after her death, in April 1906, Cap found love again. He married Elma Lockwood, who simply went by “Ma.” Ma was a force to be reckoned with—the Bonnie to his Clyde. A stocky woman with round eyes, pursed lips, and hair piled atop her head, she looked ready to fight at a moment’s notice. For Cap and their land, she often did.

In 1915, they went to jail together for selling liquor on Sundays, a trade that would be their ultimate demise. The Tribune wrote: “Streeter saw a chance to make money selling beer on Sundays to thirsty pilgrims from across the border in Illinois. Business started off briskly, but it was not long before the authorities heard about it. So one Sunday in 1915, the invaders descended in force, raided the Cap’n’s place, his castle near the foot of Chestnut Street, seized hundreds of bottles of beer, and carried Streeter and Ma off in a police ambulance.”

Historical photos capture each of them behind bars. Ma in a long housecoat with both hands gripping the bars, staring defiantly out. In his cell, Cap has his leg cocked up and one hand holding the bar. He looks morose, tired, accepting—and old. At this time, he was nearly eighty.

It wasn’t long before they were back to the district. One evening, he stepped out to address Chicago’s Dill Pickle Club: “The courts tried to get me on everything but adultery, and I beat them every time.”

He spoke too soon. In 1918, Mayor Bill Thompson ordered Cap and Ma off the district after he and Ma were caught selling liquor again. The jig was up. There were no more arguments to be made. The two retreated to a houseboat named the Vamoose just off what is now Navy Pier. Other reports say they also lived in a horseless wagon on Chestnut Street.

One day in 1921 Chicago lost its rebel by the shore. Old Cap was gone, at the age of eighty-four, succumbing to pneumonia. He was carried to his eternal resting place through downtown Chicago, his silk hat atop his coffin. For all the struggles between the two, and in a true sign of respect and of Cap’s endearing spirit, no matter how combative, Mayor Thompson paid his respects to Cap at the funeral.

Ma, who was thirty-six years Cap’s junior, committed to live on the Vamoose until she died. And she tried to keep that promise. The Tribune wrote in 1923, “She has been living on the Vamoose since 1918, winter and summer. ‘Umph! Me live in a hotel?’ she scoffed. ‘I’m comfortable here, thank you. This stove keeps me warm, and I’ll be here till I die.’”

A year later, Ma concocted a scheme. She filed a billion-dollar lawsuit against the Chicago Title and Trust company and one thousand five hundred property owners in claim of the once swampy land that was now thriving downtown Chicago. The court revealed, however, that Ma had no claim to the land as she had no claim to Cap. A year before marrying Ma, two years after Maria’s death, Cap failed to mention he had first married a woman by the name of Mary Collins from South Bend, Indiana, and never bothered to finalize his divorce. Ma didn’t see a dime (not that she would have even if the marriage checked out).

Come 1928, the Vamoose was rotted at the waterline, and the city burned it. Ma lost her home, and everything Cap was gone. She died at sixty-five years old in 1936 at the Cook County Hospital.

The legacy of George Wellington “Cap” Streeter lives on through statues, a bar, an entire neighborhood, and more in Chicago. (Photo Courtesy of Chicago History Museum)

Tall tales like Cap’s must all have their message. He represented the average man’s dream of catching a big break and benefiting from the payoff. In many ways, he got it. But we have to ask ourselves: Was Cap happy? Did he think it was worth it? His dream was not unlike others: He wanted to be rich; he wanted to be known. He was exceptional for seeing things differently, for seeing everything as opportunity. He was notorious, at least for the way he sought his notoriety.

Cap also seemed a man never satisfied with what he got. It’s quite paradoxical. It was his resolve, an endless restlessness, that got him everything he had, and everything he had wasn’t good enough. He was trading in one profession for the next, expanding upon land he got for free, and accelerating the crimes he committed along the way. It all came with a price that ended up being more than he could pay. He was known, but left with nothing.

His resolve got him everything, but everything wasn’t good enough

Inside his namesake neighborhood of Streeterville, a rental high rise was recently dubbed “The Streeter.” You can take Streeter Drive while traveling near Navy Pier. And Streeter’s Tavern on Chicago Avenue bears his name and a cartoon-like resemblance of him as its logo. They depict him as a thin man with one leg kicked up, shoes in-hand, tongue out, drinking a beer. Silk cap still atop his head.

Most monumental of all, a bronze statue of him holding Spot was erected at McClurg Court and Grand Avenue. It reads under his name, “The eccentric resident who gave Streeterville its name.”

Cap would smile at that … but then he’d stop. “Resident? … I discovered the Deestrick!”

About the author

Jamie Lynn Ferguson has lived on the west side of Chicago for nearly a decade. She serves as an advocate for anti-poverty nonprofits throughout the city, writes full-time for Catholic Charities Chicago, and is a freelance community reporter for DNAinfo-Chicago.

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