I used to catch the train out of Western Springs back in the early to mid twenty-teens. That was the tail end of what I call my Exile West of Mannheim... a stretch of life where I was working at the Board of Trade and living in Western Springs Heights or what is known as Indian Head Park, Illinois. The commute was routine, uneventful. Until one January morning when I noticed something… odd.
It was twelve degrees outside. Brutally cold. The kind of cold that stings through layers. And yet, there was this guy.... winter coat, hat, gloves… and flip-flops.
Flip-flops. During a Chicagoland winter. Every damn morning.
I watched him for a few weeks. Never changed up the footwear. Snow, ice, slush, it didn’t matter. Flip-flops. Eventually, as winter started giving way to spring, I broke the ice.
“Nice to finally have a warm day,” I said one morning, nodding down at his bare toes.
“Yeah,” he replied, “I’m gonna try to sneak in nine holes this afternoon.”
“A little golf in late February?” I smiled. “A fifty handle and a longer afternoon makes for a decent round.”
He paused. “Fifty handle? You work on the floor?”
I nodded. We had ourselves a connection.
Turns out his name was Jim. He worked in a trading office, not on the floor, but adjacent enough that we spoke the same lingo. That made us commuter buddies, and in our world, that meant something. I didn’t wait long to ask the question that had been burning since the snow first crunched underfoot.
“Alright, man,” I grinned. “What the fuck is with the flip-flops, Jim?”
He laughed. Of course it was a bet. This is trading. Everything is a bet in our industry.
He had wagered a good chunk of change that he could wear flip-flops every day for a full year.
Now, one of my first bosses taught me the hardest thing in trading was learning how to scratch a trade. Not a winning trade, not a losing trade, but just walking away even with a scratch. Flip-flop Jim wasn’t in this for a scratch. You don’t risk frostbite for break-even. No, this was a moonshot. A high-risk, high-reward play. Maybe he’d lose a pinky toe, but by God, he was bringing home a huge winner.
We kept talking that spring. Same train, same spot on the platform, same rhythm of our mornings. We had a lot in common... especially a mutual love for New Orleans. Jim and his wife had lived there for a spell, and I’d always had a soft spot for the Crescent City.
I never told Jim that my marriage was crumbling at the time. I could sense he was fighting battles of his own. His happy tone would sometimes shift when he spoke about his wife or his teenage daughters. We talked often about grabbing a beer, but we never did. Most of our friendship lived between train whistles and the hum of the rails into Chicago. We rarely crossed paths on the ride home, he always took a later train. Perk of being a floor guy was when the bell rang, the day was finished.
When I moved to Riverside, my exile ended, and so did our routine. We fell off, naturally. I figured that was that.
About ten days later, Jim called me out of the blue. I had forgotten we even exchanged numbers. He sounded relieved when I picked up. “Where’ve you been, man? I’ve been looking for you every morning.”
I told him about the move. Told him I was going through a separation. He got quiet, then frustrated. “Why didn’t you tell me?” he asked. “I could’ve helped. I had zero clue what you were going through Jumbo.”
There’s a strange kind of grief in those missed chances...
... for support, for connection, for being honest when it might’ve mattered most.
We said we’d get that beer, now that my schedule had more empty space, but we never did. Life went on, and like so many people we meet on the path, Jim drifted off of mine.
All we were, really was commuter buddies for half a year. From the bitter cold of January until the thick heat of July.
But Jim left a mark.
I don’t know if Jim ever won the flip-flop bet. I later heard that his wife had passed away. I tried reaching out to offer condolences, but I never heard back.
I hope he won that bet. I hope his daughters are thriving. I hope he found peace, or at least something close to it.
Sometimes people come into our lives just long enough to shine a little light through the cracks. That was Jim. Flip-flops and all. A strange, warm presence in the middle of a cold season I wasn’t ready to admit I was going through.
