Does Gladstone Park Even Have a Doggone History?

Anyone trying to research Gladstone Park will find there is little history — especially early history — written specifically about it. There is not even an entry for the community in the Chicago Historical Society’s Electronic Encyclopedia of Chicago, the standard for all that is relevant to the city’s roots. And the online Wikipedia, which’ll publish anything and everything, has a mere three short paragraphs on Gladstone Park. But that’s in a subheading under Jefferson Park with “Gladstone Park Station” about the historic Metra train stop in the neighborhood being the community’s only stand-alone entry. Adding insult to injury, Wikipedia gets its facts backwards by telling readers the community is named for the [William] Gladstone Park on N. Menard Avenue. The chicken did not come before the egg.

Yes, there are records from the mid- to late-1800s about the founding of Jefferson Park, within which Gladstone Park lies, when it was still an independent town and not yet incorporated into the City of Chicago. But those stories focus on the independently burgeoning commercial center at the intersections of W. Higgins and W. Lawrence with N. Milwaukee, where area farmers stopped to water their horses and pick up supplies. The settlers of Gladstone were at least a mile or two north minding their own business trading furs or, later, growing onions and other produce to sell 10 miles away in the center of Chicago. Their activities linked the community directly to downtown through Chicago’s founder, Haitian immigrant Jean Baptiste Point DuSable, the robust fur trader who became the first non-native person to settle on the banks of the Chicago River in the 1780s.

Maybe there are so few separate details about the history of Gladstone Park because its affairs were so inextricably commingled with Jefferson Park’s. But another big reason could be because the community has always been ill-defined even though it held itself separately under its different name at least 130 years ago. If one is to believe the 1891 developer’s map below, the neighborhood was already making its presence known with its bold, capitalized, and italicized “Gladstone Park” name splashed to the left of its plot plan. Identifying the first subdivision in the community at the apex of the triangle created by N. Milwaukee Avenue and N. Northwest Highway set the precedent for where it begins. From then on, disagreements over where it ends with ever-shifting north, east, and west boundaries persist. For more on this topic, see Who/Where.

Early accounts about Gladstone Park are sparsely detailed and all repeat the same few narratives. None give a convincing explanation for why the community was named after a 19th Century British Prime Minister or who had a hand in making the decision. Were there a couple of British patriots here looking to state their loyalties to the Crown or did a couple of back woodsmen celebrating over a successful hunt concoct the name as a prank, never thinking it’d stick? In the absence of new research, the knowledge of how Gladstone Park got its name may unfortunately be forever lost to history. But that doesn’t mean there isn’t a story to tell. Its gritty roots, odd triangular shape and wacky road geography as streets were added through time are all deserving of the quirky history the author was able to construct based on how the community grew.

It’s a Bird, It’s a Plane; It’s Sauganash!

All sources agree that the first settler in what became Jefferson Park was fur trader John Kinzie Clark, who built a two-room log cabin in the area in 1830. His land was south of Gladstone, however, so we can’t claim him as our own.

Around the same time Billy Caldwell, also known by his Indian name of Sauganash (roughly translated as “white man” or “Englishman”) came on the scene. The illegitimate son of a Canadian-British army officer and a North American Indigenous woman, he became Clark’s neighbor “to the north” according to Abigail Foerstner in the Aug. 6, 1986 Chicago Tribune article The Village Called Jefferson.

We have to assume this put Caldwell’s cabin in present-day Gladstone Park, although one would have to delve into more thorough records to pinpoint exactly where it was. Perhaps Peter T. Gayford’s 13 years of research that resulted in his unpublished 500-page The History of Chief Billy Caldwell — available at only a few local historical museums and Chicago’s Newberry Library — contains the definitive answer.

In any case, if Caldwell didn’t live right smack in Gladstone Park in the 1830s, all sources say he ended up owning the lands on the North Branch of the Chicago River at the very northern edge of the community. Part of this property was what later became today’s Caldwell Woods of the Cook County Forest Preserves. Meanwhile, whether as fur trader, Potawatomi Chief, or U.S. Department of Indian Affairs agent, Caldwell put his lasting stamp on Gladstone Park’s destiny.

What’s Opera Got to Do With It?

Caldwell, AKA Sauganash, had a very complicated life. The short story is that his mixed heritage (part Native American, part white man) presented both obstacles regarding his social standing and career prospects at the same time as creating opportunities for him to accomplish things few others could do at the time.

In a very sort of Madama Butterfly way, Caldwell’s mother was a Mohawk Peoples beauty when she gave birth in 1780 to the illegitimate child who became known as Billy/Sauganash, according to researchers on the now defunct Early Chicago website. His father was a British-Canadian army officer (like “Pinkerton” in the 1904 Puccini opera) who shortly afterward abandoned them, setting the mother (“Butterfly”) and child up for the tragic events that were to come. Indeed, after the senior Caldwell legally married three years later and the earlier child’s existence became known to his white woman wife Suzanne, (“Kate” in the opera), she insisted on ripping the half-Indigenous boy from his biological mother’s arms so that she and his father could bring him up themselves with English and Christian values.

When the child, originally named Thomas, arrived at the Ontario homestead of the Caldwell’s, it was only to find that one of his father’s seven subsequently-born legitimate children was also named Thomas. If his dislocation hadn’t been enough, his family unceremoniously yanked the last piece of his identity out from under him by bestowing him with the man-boy name “Billy,” all while formally educating him in English and French and raising him in the Catholic Church. Set forever on the course for how he was known and treated throughout his entire adult life, sort of accepted while definitively not, the pathos only grew.

Where is someone like former Chicago Composer-in-Residence Missy Mazzoli when you need her to gobsmack us with our own mind-blowing opera on the life of Billy (Sauganash) Caldwell?

Billy/Sauganash: A Foot in Two Worlds

While there is much myth surrounding the story of Billy (Sauganash) Caldwell, most historical researchers agree on the basic facts as presented here. When the 17-year-old half-English/half Native American crossed the border into the United States’ Northwest Territory near Chicago in 1797, it was as a Canadian-British apprentice in the fur trade. Fluent in English and French, he found for the first time that his mixed blood gave him a leg up as a negotiator with Native Americans. He learned Potawatomi and other Indian dialects and gained the trust of area tribes.

However, when Caldwell returned to Canada at the age of 32 to fight on England’s side in the War of 1812, that advantage crumbled. Even his father’s Lieutenant-Colonel creds — which had garnered officer commissions for Billy’s half-brothers — weren’t enough to earn his firstborn mixed-race son the right to serve in the “regular” army. Appointed to the British Army’s Indian Department, Caldwell instead distinguished himself by fighting valiantly to win England a substantive and brutal victory over the United States in the Battle of the River Raisin in Michigan Territory (part of the Battle of Frenchtown).

But by the time Americans in the Northwest Territory began beating back England’s Canadian Brits in this so-called Second War of Independence, the severely wounded Caldwell grew disillusioned. Always on the cusp of feeling like an outcast, he switched loyalties. His father disinherited him and he moved back to the Chicago area in 1820.

Without access to personal diaries and letters, no one can really know what Caldwell’s full motivations were as he became one of four chiefs of the Potawatomi…as well as a negotiator for the United States government’s Indian Removal program. What we do know is that in 1829 there was “much talk” in and around Chicago about pushing the 6,000 or so remaining Native Americans completely out of Illinois, according to Wayne Temple who wrote the minutely-detailed 218-page document Indian Villages of the Illinois Country: Historic Tribes for the Illinois State Museum in 1958 (revised 1966). Caldwell, respected by both sides, became one of the players who made it happen.

Representing the Council of Three Fires, the alliance of the closely-related Potawatomi (Bodewadmi), Ottawa (Odaawaa) and Chippewa (Ojibwe), Caldwell apparently tried to get the most advantageous deal he could for his people. There had already been multiple treaties — most broken — pushing Native Americans further and further from their ancestral lands as part of the great U.S. Western Expansion. By 1830 the new political reality was that the U.S. Government’s Indian Removal Act granted President Andrew Jackson the direct authority to speed the relocation of Indigenous peoples west of the Mississippi River. The country’s acquisition of 828,000 square miles of land that came with the 1803 Louisiana Purchase were what made Jackson’s plans eminently feasible, Temple wrote.

An ever-pragmatic Caldwell had already aided the Three Fires in negotiating the Second Treaty of Prairie Du Chien in 1829, with Native American tribes agreeing to relocate from the greater Chicago area to western Illinois in exchange for $16,000 and 16 barrels of salt a year. But the terms of that treaty failed to alleviate tensions between white settlers in the Northwest Territory and the tribes.

Four years later the Council of Three Fires spokesman acted again, helping hammer out the Treaty of Chicago, giving 5 million acres west of the Mississippi to the remaining Native American population in exchange for them relocating there and ceasing all claims on lands in Illinois and Wisconsin. It didn’t hurt Caldwell that the U.S. Government had spelled out in Article 3d of the Treaty that he’d get an award of $400 a year for life for his role in bringing its terms to fruition. Schedule A of the agreement also granted him $5000 outright as well as another $600 for his children. (Thanks to the Forest County Potawatomi of Wisconsin for mounting the full text of this treaty on its website.)

Presumably Caldwell thought this Treaty would be advantageous for his people, ending years of dislocations once and for all. But it suited his personal prospects as well. Putting a brave face on the future, he and three others were hired to lead a wagon train of Native American emigrants west along with a government-guaranteed $100,000 in provisions. Another $150,000 was promised for the erection of buildings and purchase of agricultural equipment in the new territory with $70,000 earmarked for education and $14,000 a year in annuities.

But the sweeteners didn’t have their desired effect. Shockingly, only 10 to 20% of tribal members (500-1000) voluntarily showed up to make the trip. And the unfortunate truth is that of those who did go, many became discontented with the new lands and some ultimately returned, according to Temple.

Strange Bedfellows Leave a Fitting Legacy

Billy/Sauganash, with one foot in both worlds, was one of the Native Americans who came back to live in the World of the White Man. Trusted by both sides even if considered second-rate by some, he had something valuable to return to right in Gladstone’s neck of the woods.

There is a dispute as to exactly why the U.S. awarded Caldwell 1600 acres of land on the North Branch of the Chicago River on the present-day border of Gladstone Park. On its sustainable development pages, the City of Chicago website claims the gesture came in in thanks for saving the life of his friend, neighbor, and fur trading partner John Kinzie Clark as well as those of his family during the Fort Dearborn Massacre of 1812. But the Community Association of Chicago’s present-day nearby village of Sauganash (named for Caldwell) says it was in gratitude for his service in negotiating the Second Prairie Du Chien Treaty.

What is for sure is that the Caldwell Reserve ran near what was called the “northern Indian line,” over which Indigenous Peoples were not supposed to tread. Created by one of many Treaties of St. Louis, this 1816 version established the northernmost boundary of a 20-mile wide strip of land that took property from the Native Americans to create a direct and strategic water passage from Lake Michigan to the Illinois River for the White Man’s exclusive use. From there they could make the vital connection to the Mississippi River, the easternmost line of the Louisiana Territory and gateway to the West since1805. The so-called “Chicago Portage” positioned Fort Dearborn (Chicago) roughly in the middle at its extreme eastern end, giving it a 10-mile buffer both north and south. The Sauganash Community Association further places the northern boundary of the passage along the village’s Rogers Avenue just north of the Chicago River. If we extrapolate, we have to conclude that the community that was to become Gladstone Park was in or very close to this northern Indian line that also defined the northern limits of the Chicago Portage.

Later in life, Caldwell sold off much of the 1600 acre reserve he had received from the U.S. Government for his contributions to help successfully negotiate the establishment of the Chicago Portage. But he kept an 80-acre tract on the corner of N. Milwaukee and W. Devon at the very edge of Gladstone Park, seemingly because he could never get a clear title to it. This is the land that became the venerable Caldwell Woods of the Cook County Forest Preserves, a most fitting legacy for this mixed-race mover and shaker to have left to the peoples of Gladstone and greater Chicago proper.

All of which might lead us to reevaluate Billy (Sauganash) Caldwell life in light of the sum total of all his activities. It’s easy to take a revisionist point of view and accuse him of being a traitor to the Indigenous tribes he was part of, giving away valuable land and getting little in return. But that wouldn’t be acknowledging the realities of the time period in which he was living, when Native Americans were lucky to get any compensation at all from a U.S. Government then operating as a ruthless occupying force. Perhaps it makes sense for Gladstone Park to recognize this smart but gritty, dependable but realistic, determined but perplexing man for what he was. Caldwell was the one who took the confusion over who he was and the challenges of how to fit in to make his way forward with great success. Aptly paving the way for the future for his peoples and himself, he blazed an original path. And perhaps became Gladstone Park’s original founding father in the bargain.

Caldwell’s dichotomy mirrors Gladstone Park’s dichotomy: half of him representing the Indigenous peoples who were stewards of our land long before the other half (American colonists) had set eyes on it. Ethnically-mixed, he was an immigrant (British Canadian) in a city that famously continued to build its strengths through a diverse immigrant population that never completely broke ties to their homelands. He was very much like how Gladstonians are today, often expressing how fortuitous they feel to live in the City of Chicago even if they don’t always feel fully of it. Intimately connected to a downtown a distant 10 miles to our southeast while equally existing on the very edge of the suburbs, we in our little community, like Caldwell, are also positioned with our feet in two worlds.

As the Crow Flies…

The second legacy Billy (Sauganash) Caldwell and his cohorts left future generations with was the network of old Indian trails that crisscrossed the community for hundreds of years until they gradually became the modern diagonal roads that so influence Gladstone Park today.

Starting in the 1600s, these five- to six-foot wide Indian pathways, located on high and dry ground, provided the only overland routes for explorers and, later, white colonists to navigate through the swampy area that was Chicago. You better believe settlers appreciated these Native American trails as a ready-made infrastructure that enabled them to travel, grow commercially and defend themselves militarily.

But authorities long undervalued the local Indian trails as the vital cogs they were, as discussed extensively by Tanner Howard in Native American routes: the ancient trails hidden in Chicago’s grid system, The Guardian, Jan. 17, 2019. These routes were so taken for granted that documentarians didn’t even chart them until 1900 when cartographer Albert F. Scharf was the first to reconstruct the area as it existed in 1804 on his map “Indian Trails and Villages of Chicago.”

The old Indian trails were given so little heed that when permanent (white) settlers began moving to the area in earnest in the 1830s, they didn’t make plans for how they might fit in with their European notions about growth. As the the commercial center of Jefferson Park expanded to 50 buildings by 1855, town leaders felt the pressure to more efficiently organize their village in standard western ways. Formally platting out a street grid of parallel and perpendicular roads, they incorporated as the Town of Jefferson in 1872, according to the Electronic Encyclopedia of Chicago.

That’s when the road system began to go awry. There was no thought to abandoning the old diagonal Indian trails that ran into the area because they were some of the most direct and dependable routes into the big city. But nobody was sure how to integrate them appropriately with the new straight thoroughfares that were being laid to run into the community or the rectangular blocks that were filling up the spaces in between.

While the roads intersecting at various angles were creating a bit of confusion leading into Jefferson’s town center, it was in Gladstone to its north that the problem had the potential to become more critical where the old slanting roads had already been splitting and merging at their most acute angles. As long as the acreage on the outskirts of town was kept in tracts of farmland, it wasn’t a huge issue. With the onion business thriving in the glacial lakebed soil (black topsoil over mucky clay that had supported the wild, garlicky onions native to the area), there was little thought that the large plots would be good for any other application. After all, these same stinking onions, rendered “Chicagoua” by the French in a mispronunciation of the Native American word for them, was what had given Chicago its very name. And who would want to build homes or businesses in what was essentially glorified swampland?

But things were changing by the 1880s when the City of Chicago, determined to grow into a metropolis, came knocking at the doors of northern and western towns then outside its borders. Officials had seen the population exploding in these areas seven, eight, nine, ten miles from the city center and hankered to possess them. Indeed, by 1884 the Town of Jefferson itself had boomed to 500 residents, mainly of Polish and German descent, according to the Electronic Encyclopedia of Chicago. By then, nearly a dozen streets to the north in the area known as Gladstone Park had been platted between N. Northwest Highway and N. Milwaukee as evidenced on the map seen earlier. And more new roads were needed.

When Chicago dangled the prospect of better services for less money to independent municipalities struggling to provide water, electric, and sewer as well as run schools and maintain roads for increasing numbers of people, voters approved. In 1889 the Town of Jefferson along with many other villages let the city gobble them up in a grand annexation of 125 square miles and 225,000 people, as seen in the map below. Jefferson Park and the small section within it to the north that became Gladstone Park were swept up en masse. The die was cast.

As the city improved transportation to and from the Far Northwest section of the growing city, housing followed. More and more farmers started to divide and sell their land. Meanwhile, in 1909 Chicago had adopted its seminal Burnham Plan that established an orderly arrangement of streets for the whole city. New main arteries were to be perpendicular (north-south) or parallel (east-west). A grid system forming blocks with streets at right angles to each other was prescribed as the most effective way to encourage growth. Further organization was to come in a clever alphabetical naming scheme starting at Lake Michigan with names beginning with “A” and progressing west. For a complete discussion of these initiatives and the results of them, see Streets.

In a Law of Unintended Consequences sort of way, the new straight roads sliced Gladstone Park’s three heavily-traveled diagonal arteries into odd-angled intersections of two, three or more roads, creating havoc. Compounding the problem was the fact that the slanted streets, crammed together within a half mile, were all at different angles to each other. So when land developers began subdividing more tracts of land between the diagonal and straight roads to try to create the most salable rectangular lots within the recommended grids, it often became a game of pounding square pegs into round holes.

The end result: a patched-together quilt of roads with sections of tilted blocks alternating with straight ones and random streets intersecting at inconceivable angles. Everywhere a straight road met a diagonal, there were leftover pieces of land in odd shapes such as slanted parallelograms, irregular quadrilaterals and triangles in scalene, isosceles and obtuse form. Some of these are pictured in the Vintage Living section.

How in Heck Did Gladstone Park Get Named after a British Prime Minister?

This might be the most important question of all, but it’s the one with the fewest answers.

Like a box in a box, Gladstone Park’s marvels and curiosities have long been encased within the larger neighborhood of Jefferson Park. But as one of over 200 smaller amorphous areas within Chicago’s 77 official neighborhoods that were unified by different attributes and goals, Gladstone has also been its own entity. Maybe its square mile of land never had size or stature, but it has always had its own distinct personality.

Although all authorities agree the area was named for British Prime Minister William Gladstone (1809-1898), there is little verifiable documentation on how the designation came about. Earlier settlers such as Billy (Sauganash) Caldwell, who started building their cabins in the area in the 1830s and 1840s, were English traders and hunters from what was then known as British North America (Canada). So there might have been an affinity for the English homeland that persisted when the highly-regarded Gladstone began serving his four terms as prime minister in England in1868, only one year after the birth of the (more independent) Canadian Confederation.

Records are sketchy on how and exactly when Gladstone Park separated itself out enough to become its own unmistakable area. Some of the earliest authoritative records on the use of the name come from records of the Chicago Park District. After the Jefferson Park District first received a request in 1923 from the Gladstone Park Community Club to locate a park in what was called the Gladstone Park Subdivision, the (William) Gladstone Park on N. Menard came to be in 1930.

The community’s name might have further gotten cemented in people’s minds once they could get on and off the train right in their neighborhood at the new (1920) Gladstone Park Station off N. Austin on what is now the Union Pacific/Northwest (Metra) Line.

More research definitely needs to be done to pin down how Gladstone Park came to be named after one of Great Britain’s most famous prime ministers. It’s a particular conundrum as the choice went against every trend in America’s history ever since the mid-1770s when the country had battled so hard against England — in two wars — to gain its independence. Indeed, when new American towns were popping up everywhere in the mid- to late-1800s, patriotism ran high with slews of new communities naming themselves after U.S. Presidents, statesmen and generals. The town in which Gladstone has long been part of was no exception. Seeking first to name itself after fifth U.S. President James Monroe, it was disappointed to find a small southern Illinois town had already beat them to the punch. So community leaders settled on their second choice and applied to become the “Town of Jefferson” after founding father and third U.S. President Thomas Jefferson. After Chicago annexed the municipality. the name stuck on the greater neighborhood as “Jefferson Park.” Otherwise, Gladstone Park might instead be part of Monroe Park today!

In a fitting tribute to the official neighborhood name, there is a bust of Thomas Jefferson on display at the Jefferson Park Transit Center south of us on N. Milwaukee near W. Lawrence. One would be hard pressed, though, to find a bust or painting or inscription to honor William Gladstone in Gladstone Park. Perhaps if the community could discover more about just why it aligned with English Prime Minister William Gladstone for its identity, the community would be able to acknowledge its distinctive choice, develop a better relationship with its namesake, and be even more “Gladstone Proud.”