If you look at a map of Chicago, you'll quickly figure out that it's set up like a grid. A sheet of graph paper. A marvelous thing when you're a limo driver in a hurry, as the numbering system for addresses is the purest form of simplicity. State and Madison is 0 North and 0 West and the entire city fans out from that point with numbers increasing as you move away from the center of the city.
On the northwest side, where I've worked for the better part of 35 years, there are exceptions to the foolproof method of self-location.
Diagonals.
Elston Ave., Milwaukee Ave., and Caldwell Ave. all cut northwest through the heart of the grid.
I've always been fascinated with Chicago history, and the diagonals.
I was curious as to why the anal-retentive city planners (and yes I'm looking at you Daniel Burnham) would ruin an otherwise perfect blending of form and function.

In the late 1820s, a young man came to Chicago from Detroit. The son of an Irish-Scot father and a Pottawatomie mother (some say Mohawk), he was known as Sauganash. Educated at The Jesuit School in Detroit, he spoke French, English, and his mother's native Pottawatomie.
He was befriended by one of the original Chicago merchants, Mark Beaubien. Beaubien himself was the son of a French father and Pottawatomie mother, which may have contributed to their friendship (Beaubien Street in the Loop is just east of Michigan Ave. and is about three blocks long. Most people here have no idea who it's named after but that's another post.)
That area of Chicago was the heart of a small Indian village back in 1820, when Sauganash came rolling into town. Perhaps Indian village is a stretch, but the Ottawa, Pottawatomie, Chippewa and leftover Black Hawks were much more numerous than the newly arrived white folk, and within the city there was ongoing intercourse between settlers and native Americans. Trading furs and goods back and forth, crops exchanged for whiskey, Chippewa chiefs, French fur trappers, English settlers all elbow to elbow at the bars. The original melting pot.

Beaubien thought so much of Sauganash that he named a hotel after him, the first of its kind in Chicago. It's said that Beaubien used to greet mud-covered travelers with a blanket, and lead them to a vacant spot on the floor. While taking payment for the night's lodging, Beaubien would warn the lodger to "watch out for the Indians, they'll try stealing the blanket." Once the lodger was sound asleep, Beaubien would gently peel the blanket off the travel-weary snoozer, and sell it to the next guy in the door.
Beaubien's Tavern (on what is now Beaubien Street) was a meeting place for the social climbers just in from the east coast. Young men by the boatload came down the St. Lawrence, through the Erie Canal, and from across Lake Michigan, while wagonloads arrived via the 2000 mile rut-filled muddy trail that came around the southern tip of the lake by what is now Gary, Indiana. They came here to work hard and get rich. And sleep on the floor of the Sauganash Hotel.

They would gather at Beaubien's to talk current events, like the proposed US Government buyout of the Indian land they were all standing on.
(Less than 30 years later, in a building called the Wigwam, on the very same land formerly occupied by the Sauganash Hotel, Abraham Lincoln was nominated at the 1860 Republic Convention.)

In September 1833, the US government called a grand council in Chicago of the 77 chiefs of the Chippewa, Ottawa, and Pottawatomie tribes. On Sept 26th, a treaty was signed with 76 chiefs affixing their marks and one, Sau-Ko-Nock, his name to the formal agreement.
For the next two years, an annuity was paid to the tribes within the city itself. After that, the payment of goods would be delivered to the Indians at their new home....west of the Mississippi River.
The annuity consisted of food, blankets, pots and pans, and assorted other goods that were distributed by piling the stuff in mounds on the west side of the Chicago river near what is now the intersection of Randolph and Canal Streets.
The first payment was made in 1834, and the Indians were made to sit in a large circle around the mounds of merchandise, and it was literally thrown to/at them. The morons who were in charge of distribution lost all control and soon the Indians were all over the small mountains of goods.
When the distribution was completed, the Indians then bartered away what they'd just been given for clothing and whiskey from the traders waiting nearby.
The final payment to be made (in the city) in 1835 was a much more dramatic event. Indians by the thousands gathered on the edge of the city in full ceremonial splendor. Faces painted, and with eagle and hawk feathers knotted into their hair, they came on horseback and on foot. Their numbers dwarfed that of the white residents of Chicago.
They knew that this was their final day as the caretakers of this land, and the idea that a government would claim actual ownership of land enraged them. Before leaving the country of the Illinois, they would leave an impression on the strangers who had settled in the land they'd occupied for generations.
A thousand warriors gathered at the council house on the river's north side and began to march into the heart of the city. They carried clubs and tomahawks. As they entered what is now The Loop, their music makers began chanting and banging their drums. They slammed large sticks together as they gathered for a War Dance.
The column of warriors poured into the city and went street by street, shouting and shrieking their dislike for those who now called Chicago their own.
People were scared shitless, and stayed locked in their ramshackle homes, peering out through the blinds and expecting the worst. An Indian uprising.
John Dean Caton, who later became Chief Justice of the Illinois Supreme Court witnessed the event from the Sauganash Hotel. He described what he saw as "all the worst passions which can find a place in the breast of a savage- fierce anger, terrible hate, dire revenge, remorseless cruelty...."
It was only afterward, and to his great relief, Caton realized it was only a demonstration of Indian might, designed "to test the nerve of the stoutest." Given the overwhelming force that the Indians possessed, Caton noted that had they actually attacked the city, "They would have left not a living soul to tell the story."
And then, the Indians withdrew from the city.
Much has been speculated about the role of mediator that Sauganash played in helping prevent a massacre in 1835. He is said to have had big cred within the community. The Indians knew he was able to speak and write in English and French. They knew he was friends with Mark Beaubien.
The white men knew he was Jesuit educated and that his father was a white man. Rumors of Sauganash's connection to Tecumseh and his life as a chief in Michigan were never confirmed, but the white men used that propaganda to convince Washington that they had "their man" in Sauganash.
Sauganash is actually a butchered version of the native American term for Englishman. Mark Beaubien and the white power brokers in early Chicago actually called him Billy Caldwell.

Caldwell Ave. and Milwaukee Ave. are diagonals for a very simple reason.
They were here first.
They were here long before Daniel Burnham and the other city planners laid out the orderly grid pattern on top of them.
They were Indian trails that pre-dated the white settlers.
Today, if I leave my office and drive south on Milwaukee Ave, I can cut east on Touhy and pick up Caldwell Ave. About a mile south of there, Caldwell curves over the Edens Expressway, right at the edge of the lovely little Chicago neighborhood known as Sauganash, bordered on the west by Cicero Ave.
And Caldwell Ave. named for Archibald "Billy" Caldwell now sits directly atop the route used by the Ottawa, the Chippewa, and the Pottawatomie as they departed Chicago, forever, 175 years ago.
