Portland was our undoing.
It had started so simply. A boys’ night out. A business trip with just the right amount of bad decisions sprinkled in. Scott Wicklund and I weren’t supposed to be here. He had a Bible-study wife, two kids—one of which didn’t even look like him—and a home that reeked of store-bought stability. Me? I was unhappily married, drinking like I was trying to sink something that refused to go under.
Portland, though—Portland had answers for men like us.
We hit the ground running. Whiskey, IPAs, bad decisions stacking up like unpaid bills. Business first, then pleasure. That was the lie we told ourselves.
Our first stop was The Acropolis. Or, as I called it, The Necropolis. A strip joint disguised as a dive bar disguised as an abandoned fish-and-chips shop. Outside, a flickering neon sign that promised a five-dollar steak. Inside, a place where dreams had come to die—where women with stretch marks and dead eyes danced not because they wanted to, but because they had nowhere else to go.
I liked it that way.
Scott? He was unraveling.
He dove headfirst into it, ordering dances like he was making up for years of missed sin. He had the hunger of a man who had spent too long suppressing himself. I knew the type. The ones who spent their lives saying “yes, dear” and filling out tax forms. Eventually, they crack. And when they do, they don’t just dip their toes into the abyss—they swan dive into it.
I wasn’t much better. I drank. Hard. Unapologetically. If Scott was a man chasing the thrill of sex, I was a man trying to drown himself in the bottom of a glass. We made a hell of a pair.
By 3:30 AM, we were being shoved out the door, and we stumbled into the airport with the grace of two men who had no business being awake.
We had a property deal waiting for us in Utah, a little piece of commercial real estate I had sniffed out. It was supposed to be a serious trip, a step toward something responsible. But the only thing serious about us at that moment was how goddamn drunk we were.
I passed out in the conference room. Mid-negotiation. One second I was talking prices, the next I was out cold. When I came to, I had somehow managed to haggle the property down to $600,000 from the original $720,000. I still don’t know how I pulled that off.
Then we landed back in Portland. And, of course, we did the only logical thing.
We started drinking again.
~
Portland had done something to Scott.
You could see it in his eyes, in the way he carried himself. A man possessed. A man who had seen too much and wanted more.
He called me constantly.
“Let’s hit Portland again, man. One more time.”
I had kids, responsibilities, a wife who didn’t give a shit as long as the bills got paid. I had just enough restraint left to say no.
Scott? He went alone.
That’s when things got interesting.
He was past strip clubs now. He wanted more. He found a number, set up a meeting.
An escort.
She was Polish. Cold, striking, the kind of woman who looked through you instead of at you.
He knocked on the door, expecting a transactional encounter, expecting an experience he could write off as “just another night.”
Instead, he got something else.
A noise.
Upstairs.
Footsteps.
“Is someone else here?” he asked.
“No,” she said.
Bullshit.
Then he saw it.
A ball-peen hammer on the nightstand.
Now, I’m no expert in interior decorating, but I’m pretty sure a hammer next to the bed isn’t a good sign.
His stomach turned.
Something was off.
Something was very, very off.
He got up.
“I have to go,” he said, already moving toward the door.
She followed, her voice suddenly more insistent. “Wait, where are you going?”
But Scott was already out the door, already peeling out of the driveway like the goddamn devil was chasing him.
~
His phone rang.
It was her.
“Sssccoooottt,” she purred.
Something in her voice sent a shiver down his spine.
“Where are you? You owe me.”
“I didn’t feel comfortable.”
“You owe me.”
“No, I—”
“I don’t give a shit what you felt. You wasted my time. That costs money.”
Scott hung up.
Two minutes later, she called again.
This time, her tone had changed.
“Are you Scott Wicklund from Bend, Oregon? The one who owns the commercial real estate on—”
Scott froze.
She had Googled him. Found his home address, his business, everything.
“Are you sure you don’t owe me?”
That was all it took.
Scott flipped the car around, drove right back, threw the cash at her, and left.
~
You’d think that would have scared him straight.
It didn’t.
If anything, it made him worse.
He wanted more now.
More strip clubs. More bars. More nights lost in bad decisions. He was coming unglued, spiraling toward something that couldn’t be undone.
Home life and personal life were two different planets now.
He was crumbling.
It was just a matter of time.
~
At first, it’s a thrill. A secret. A game. A thing you do in the shadows.
Then, before you know it, the shadows are all you have.
Scott had started as a real estate guy with a good reputation. A family man. A proper dude.
Now?
He was one bad decision away from losing it all.
Portland had ruined him.
Or maybe, just maybe, it had revealed who he really was all along.
