Three Hundred and Sixty Degrees

American Friendship Historical Fiction

Written in response to: "Start or end your story with the line “I should have known better.”" as part of Not What It Seems.

Three Hundred and Sixty Degrees.

I should have known better. That’s the story of my life. Perhaps I did know better, but I didn’t care enough at the time. Funny how that happens. You think you’re making small choices, but they turn out to be the ones that shape everything. Anyway, here we are, and it’s a wonderful day. If you can spare the time, I’ll tell you a story. Everyone likes stories with a happy ending, or at least one that has a point.

What I’m about to tell you has the truth to commend it. My recollection of these events is so vivid they might as well have taken place yesterday. Time doesn’t fade things the way people think it does. It just turns them, slowly, like this roundabout I’m sitting on.

My apologies, I failed to introduce myself. I’m Jacob Donaldson, a carpenter by trade. Every day, I come to Ellis Park and, more often than not, talk to myself. Well, I’ve little else to do. Most people ignore me and pretend they can’t see me. Once, I was young and carefree like you, but that was a long time ago. Now I sit here on a children’s roundabout, looking, reflecting, talking to those who pass. It’s springtime, a time of year I love. The freezing winds of winter have departed, and we have those wondrous hot summers to enjoy.

Oh, I forgot to tell you where we are: Chicago. It’s larger now, but it hasn’t been around long, not really. In 1833, three hundred and fifty people subsisted here, and if my memory serves me well, that was the first time the town was mentioned in American history. Many have said the name originated with the Indians, but no one knows for sure. History tells us that Jean Baptiste Du Sable, an African American from Haiti, was the first settler. I’m told he was a runaway and met his wife, an Indian lady, not far from here. Together, they built up a large business. He worked long hours as a carpenter, cooper, miller, and distiller of good whisky. A man after my own heart, hands always busy, mind always planning.

Yes, the town has had its fair share of problems since it began. A few I remember well. The cholera epidemics were horrific. I was a young man, strong as an ox but not tough enough to carry the weight of what I saw. A fool of a captain in charge of an immigrant ship didn’t recognise the disease, and as a result thousands died. I helped build makeshift shelters for the sick. I hammered nails with hands that shook. I lost my friend Samuel, a cooper who could shape a barrel so perfect it looked like it had grown that way. He died in a week. I still think of him when I smell fresh-cut oak.

The Great Fire reminds me of the Great Fire of London, but not half as shocking. It started on a Sunday night and continued burning into Monday. I remember standing on a rooftop, watching the sky turn the colour of molten copper. Thankfully for the city, it rained at midnight of the second day, which put out the last of the flames. The number of casualties reached three hundred. I helped rebuild houses for the homeless. Strong, sturdy ones. People needed something solid to hold on to.

Ah, I almost forgot to mention the monster of 63rd street. That man was evil. He put to death thirty citizens we know of, but he is suspected of murdering hundreds of others. They buried him so deep he’ll never get back. I remember the fear on mothers’ faces in the neighbourhood. Children never ventured outside to play, and full-grown men walked home in groups. Chicago has its dark shadows, but that one was darker than most.

Good morning, Mrs Adams. I’m really glad to see you. How are you today? You’re looking well. Are you still writing those books? Can’t you stop and chat? Okay, perhaps later. A prominent woman is our Jane. She loves kids and people, worked hard for world peace, and received the Nobel Peace Prize in 1931. I once repaired a doorframe at Hull House. She thanked me as though I’d built the whole place myself.

Wait a minute, here comes a father with his small child who wants to go on the roundabout. I’ll move to the swings. Few parents bring their kids to the park these days. Joggers and those mad skateboarders charge around during the morning, but what with the drug addicts and muggers, I don’t blame them. I’m here because there’s nowhere left to go. After dark, the place is deserted, except for that strange lot who get up to queer things in the bushes. I never judge. It takes all sorts to run a city, and people find comfort where they can.

I spy Harold Washington; he often stops for a chat. Every day he takes his morning march around the park. What a great guy he is. Made mayor twice. Not bad for a Black man in those days, and he was good. Fairer than most. They even named a library after him. Nice day, Harold, oh, you’re on your way to a meeting. Don’t overdo it now, do ya hear?

Ah, here’s my hero, Alphonse. As a young man, he worked hard and went home to his mother every night. Many say he was a nonentity, but my, how he could dance. His life changed when he got a bartending job at Frankie Yale’s bar. Prohibition became the means for his rise to power.

Al Capone, the son of Italian immigrants, became the infamous gangster of Chicago. I saw him once. He wore a sharp suit and walked like a man who expected the pavement to move out of his way. As we know, the law imprisoned him for tax evasion. Pathetic when you consider his reputation. Okay, Al, you’re in a rush; talk when you have more time.

One more go on the roundabout. Three hundred and sixty degrees, and then I must head off to town. You must see the sights. They’re quite something. The water tower is amazing, but then so is Sears Tower. Did I mention that skyscrapers originated in Chicago? I helped build one of the early ones, not the fancy steel frames, but the wooden scaffolding that supported the workers. I remember the wind at that height, how it tugged at your coat like a mischievous child.

Tell you what, if you go for a walk, enjoy what you see. Chicago is a city that keeps reinventing itself. Every time you think you’ve seen it all, it turns again, like this roundabout, showing you something new.

The roundabout creaks as I push off with my foot. It turns, giving me a full circle of the park. The joggers, the trees, the old bandstand, the swings, the path leading out to the street. Three hundred and sixty degrees. A full life. A full city. A full story.

When the roundabout stops, the world feels quieter, as if it’s listening. I take in the view one last time. I love the sunlight on the grass, the distant hum of traffic, the laughter of a child who doesn’t yet know how precious laughter becomes.

Me, I stay just across the way. That’s my patch. When you consider the price of land these days, I’m more than pleased. My grandchildren bought that slab of white marble as my marker. They visit sometimes; I hear their voices when they come. They talk about me as though I’m gone, but I’m right here. Always have been. Always will be.

So, if you ever find yourself in Ellis Park, take a moment. Give the roundabout a gentle push. Let it turn. Let it show you the city the way it showed me. One slow circle at a time.

And if you feel someone watching over your shoulder, don’t be afraid. It’s only me, Jacob Donaldson, carpenter, Chicagoan, still enjoying the ride.

Posted Jul 31, 2026
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3 likes 1 comment

August 05, 2026 09:08

I really liked how you wove Chicago’s history into Jacob’s personal memories; it made the city feel alive and meaningful. The roundabout was a powerful, memorable motif that served as both a physical landmark and a symbol of the cycles of life, memory, and community. The ending was moving and unexpected, adding emotional depth. Great work!

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