
Chicago has always been my kind of town.
I’ve been there more times than I can remember, usually for work, and I’ve never regretted a single trip. There’s something about the place that feels familiar to me. The buildings, the people, the elevated trains rattling overhead. Even the wind coming off Lake Michigan seems to have its own personality.
Here I was again, alone, in town for another round of software training for the hospital where I worked.
I’d traveled alone plenty of times over the years. In fact, I preferred it. There was something liberating about arriving in a city where nobody knew you and having a few evenings completely to yourself.
Outside of the software training there were no obligations or itinerary. It was just me, The Windy City, and an expense account.
I’d just finished dinner at the original Pizzeria Uno, where I’d demolished my usual Chicago Classic deep dish and washed it down with my favorite IPA.
And yes, I said the original Uno.
Forget those chain restaurants scattered around the country. Those are distant cousins who show up at family reunions and pretend they’re part of the immediate family. If you’re ever in Chicago, go to the original. Sit at the bar and order the deep dish.
You can thank me later. Although after consuming several pounds of cheese, sausage and dough, you might want to wait until your arteries reopen.
After the bill was paid I waddled outside into the crisp evening air and started walking.
I had nowhere in particular to go, having already checked into my hotel earlier in the day. The conference didn’t begin until the next morning, and my only real decision was whether I’d be able to squeeze in a Cubs game sometime during the week. That depended entirely on when the sessions ended and whether one of the vendors announced those two magical words every conference attendee loves to hear:
“Open bar.”
As I walked, I noticed something on the sidewalk ahead of me. At first, I barely gave it a second thought. Then I stopped.
It was a phone booth. An actual phone booth.
Not some decorative prop outside a retro restaurant, or something converted into a Wi-Fi hotspot or Instagram backdrop. A real, honest to goodness phone booth.
It even had the word “TELEPHONE” emblazoned across the top, just like I remembered.
I stared at it like I’d just stumbled across a living dinosaur.
For anyone born sometime after the first iPhone, allow me to explain. There was once a time when human beings left their homes without carrying a telephone in their pockets.
I know.
Terrifying.
If you were out and needed to call someone, you actually had to find a telephone.
And as a kid, I loved them.
We had one of those heavy rotary phones at home. You’d stick your finger into the little plastic hole corresponding with the first digit of the number you wanted, rotate the dial clockwise until it stopped, let go and watch it slowly click its way back.
Then you’d do it again.
And again.
Seven numbers.
Calling someone required commitment.
One day my aunt actually got one of those fancy push-button phones. She was basically living in the future, or so I thought.
Of course, my favorite number to dial was always zero, because dialing zero got you a live operator.
I’d sit at home on rainy Sunday afternoons and dial it for absolutely no reason whatsoever. The calls always went something like this:
“Operator. How may I help you?”
Giggle.
Click.
Then I’d do it again.
“Operator. How may I—”
Giggle.
Click.
Usually by the third or fourth time, the operator would call back and inform my father that one of his children was abusing the telephone system.
That particular conversation rarely ended well for me. But the following Sunday, I’d do it again.
Some temptations were simply too powerful.
The telephone also introduced me to another childhood vice: those late-night commercials advertising numbers like 976-JOKE.
“Call now!”
And I did.
Repeatedly.
Apparently, 99 cents a minute adds up when you’re a kid listening to terrible prerecorded jokes.
Dad discovered that lesson when the phone bill arrived. I learned a completely different lesson shortly thereafter.
Funny now. Not so funny then.
Years later, Dad and I actually laughed about those stories.
It was near the end of his life. He was lying in a hospital bed, IV lines running into his arms, morphine doing its best to keep the cancer from hurting him more than it already had.
Somehow we started talking about the old days.
The operator.
The joke line.
The phone bill.
The punishment that followed.
Dad started laughing.
So did I.
For a few seconds, he wasn’t a dying man in a hospital bed and I wasn’t the grown son trying desperately not to think about what was coming.
We were just father and son again. Laughing about something stupid I’d done as a kid. For those few seconds, cancer didn’t exist.
Dad died not long afterward.
It’s funny what memories stick with you.
Standing on that Chicago sidewalk years later, staring at an old phone booth, all of it came rushing back.

This particular booth even had a phone book dangling beneath the telephone by a little metal chain.
A phone book. Now there was another extinct species.
I stepped closer.
The pages were yellow and curled, and the cover was torn nearly in half. I wondered how old it was.
1998?
1996?
Maybe older.
I reached toward it to find out.
The telephone rang.
I froze.
For a moment, I thought I’d imagined it.
Then—
RING.
I looked around.
People were walking farther down the street, but nobody seemed interested in the phone.
Who the hell calls a pay phone anymore?
Better question:
Who even knows the number?
RING.
The nine-year-old inside me immediately took control.
I stepped into the booth.
The smell hit me first.
Old paper. Stale beer. Decades-old cigarette smoke embedded into the booth’s glass walls.
I suddenly remembered why phone booths disappeared.
They were disgusting.
RING.
I reached for the receiver.
For some reason, I decided that whoever was calling deserved a little entertainment.
I lifted the phone to my ear.
“Dave’s Pizza,” I said. “We deliver. Can I take your order?”
Silence.
I smiled.
This was going to be fun.
Then I heard breathing.
Slow.
Shallow.
Labored.
My smile disappeared.
“Hello?”
More breathing.
Something changed inside the booth.
The sounds of Chicago seemed to disappear. The traffic. The voices. The distant rumble of the train.
Everything.
Gone.
Then came the voice.
Weak.
Familiar.
Impossible.
“Jimmy?”
My hand tightened around the receiver.
Every hair on my arms stood straight up.
“Jimmy… it’s me.”
My heart stopped.
For one impossible second, I was no longer standing inside a phone booth in downtown Chicago.
I was sitting beside a hospital bed.
Listening to my father laugh.
Watching morphine drip through an IV.
Knowing there were things I still wanted to tell him.
Things I thought I’d have more time to say.
I pressed the receiver tighter against my ear.
“Dad?”




Leave a comment