“The Carriage Heist”

The sewers beneath the Slink reeked of desperation and greed. Marcus pressed his palm against the cold stone wall, feeling the dampness seep through his gloves as he listened to Semyon’s pitch. The recruiter’s voice carried across the underground trading floor, but there was something off about his usual confidence.

“Armored caravan tomorrow at dawn,” Semyon announced to the gathered thieves. “Rich pickings for those brave enough to take the risk. My best operative will lead—Pearl Fraley.”

Marcus had heard the name whispered in taverns and spoken with reverence in the shadows. Pearl Fraley, the ghost who could slip past any guard, the shadow who never left witnesses. If she was involved, the job was worth considering.

“What’s our cut?” called out Vera, a scarred woman who’d lost two fingers to a merchant’s blade.

“Forty percent for the crew,” Semyon replied, his eyes scanning the crowd. “But Pearl’s particular about her partners. You’ll need to convince her you’re worth the risk.”

An hour later, Marcus found himself in the cramped confines of the Bounty Hunter Hotel, facing the legendary Pearl Fraley across a rickety table. She was younger than he’d expected, with auburn hair pulled back severely and green eyes that seemed to catalog every detail of his appearance.

“So you want to rob a caravan,” she said, her voice carrying a slight accent he couldn’t place. “Tell me why I should trust you with my life.”

Marcus leaned back in his chair. “Because I’ve been studying that route for weeks. I know every guard rotation, every chokepoint, every escape route between here and the city gates.”

“Impressive preparation.” Pearl’s fingers drummed against the table. “What makes you think this particular caravan is worth the risk?”

“Gold shipment from the northern mines,” Marcus replied. “Enough to buy half the rough part of town. But it’s the timing that matters—they’re moving it during the festival when most of the constables are busy with crowd control.”

Pearl nodded slowly. “I’ve heard similar reports. Very well, you’re in. But we do this my way, understand? I’ve survived this long by being careful.”

They spent the next three hours planning the heist. The caravan would pass through Merchant’s Row just after dawn, taking the wide thoroughfare to avoid ambush points. But there was a section where the road narrowed near the old temple—a perfect spot for their trap.

Marcus would create a distraction at the front of the convoy while Pearl approached from behind. Quick, clean, profitable. Everything a good heist should be.

“One more thing,” Pearl said as they finalized their plans. “I work with a small team of specialists. They’ll be positioned around the ambush site for support.”

“More thieves?” Marcus asked.

“You could say that.” Her smile was enigmatic. “They prefer to stay in the shadows.”

Dawn broke gray and cold over the city. Marcus positioned himself at the designated spot, dressed as a street sweeper with a cart full of refuse that could be quickly overturned to block the road. The weight of his concealed daggers was reassuring against his ribs.

The caravan appeared through the morning mist like a merchant’s dream made manifest. Four heavy wagons pulled by sturdy horses, surrounded by a dozen guards in mail and leather. Exactly as their intelligence had indicated.

Marcus began his performance, sweeping debris into the center of the road with exaggerated clumsiness. As the lead wagon approached, he stumbled, spilling his cart directly into their path.

“Sorry! So sorry!” he called out, scrambling to collect the scattered refuse. “Clumsy old fool, that’s what my wife calls me!”

The guard captain raised his hand, bringing the caravan to a halt. Two soldiers dismounted to help clear the obstruction, their attention focused on Marcus and his theatrical bumbling.

Perfect. Pearl should be moving into position now.

But as the seconds ticked by, something felt wrong. The guards were too relaxed, too confident. And where was the signal that Pearl had reached the rear wagon?

“Need some help there, grandfather?” The guard captain’s voice was friendly, but his eyes were sharp as he studied Marcus’s face.

“Just need to clear this mess,” Marcus replied, maintaining his act while his mind raced. Where was Pearl?

“Don’t worry about it,” the captain said, his hand moving to his sword hilt. “You won’t be going anywhere.”

The world exploded into chaos. Guards emerged from concealment all around the ambush site—not Pearl’s promised specialists, but constables in official colors. They moved with military precision, surrounding Marcus with a ring of steel.

“Marcus Holloway,” the captain continued, his friendly mask falling away, “by order of the Crown, you’re under arrest for conspiracy to commit robbery.”

Marcus’s blood turned to ice. They knew his real name. This wasn’t a failed heist—it was a trap.

“Looking for this?” Pearl Fraley stepped out from behind one of the wagons, holding up a constable’s badge that gleamed silver in the morning light. “Constable Pearl Fraley, Special Investigations. Thank you for making this so easy.”

The betrayal hit Marcus like a physical blow. Everything—Semyon’s nervousness, Pearl’s “specialists,” the convenient timing—it had all been orchestrated.

“How long?” he asked, his voice barely above a whisper.

“Six months,” Pearl replied, not without a trace of what might have been sympathy. “I’ve been building cases against half the thieves in the Slink. You were just the first domino to fall.”

Marcus looked around at the ring of constables, calculating odds that grew worse by the second. But he hadn’t survived fifteen years in the underground by giving up easily.

“Semyon?” he asked.

“Under arrest as we speak,” Pearl confirmed. “Along with most of his network. This operation has been in planning for months.”

“The Thief Lord?”

“Scarrow Eck is next on our list.” Pearl’s smile was cold as winter. “The rough part of town is about to become much more civilized.”

Marcus nodded slowly, then dove to his left.

He rolled behind the overturned cart as crossbow bolts splintered the wood around him. His daggers appeared in his hands as if by magic, and he came up throwing. The first blade took a constable in the shoulder, spinning him around. The second found the gap in another’s armor.

“Alive!” Pearl shouted. “We need him alive!”

But Marcus had no intention of being taken. He sprinted toward the narrow alley between two shops, using every trick he’d learned in a lifetime of running from the law. Behind him, boots thundered on cobblestones and voices shouted orders.

The alley led to a maze of back streets and hidden passages. Marcus knew these routes like a spider knows its web, but the constables had come prepared. At every turn, he found his escape blocked by more guards.

They herded him like a wolf driving prey, cutting off options until he found himself trapped in a dead-end courtyard behind a baker’s shop. The walls were too high to climb, and the only exit was blocked by a dozen constables with drawn swords.

Pearl entered the courtyard last, her crossbow trained on his chest.

“It’s over, Marcus,” she said. “Surrender now, and I’ll put in a word with the magistrate. You might live to see another sunrise.”

Marcus laughed, surprising himself with the sound. “You really think this ends anything? There will always be another thief, another job, another score to settle.”

“Perhaps,” Pearl acknowledged. “But there will be fewer of them after today.”

“You don’t understand what you’ve destroyed,” Marcus said, his voice growing harder. “The Slink, the thieves, even the gangs—we keep order in the rough part of town. We handle problems the constables can’t or won’t touch. Remove us, and something worse will take our place.”

“We’ll see.” Pearl’s finger tightened on the trigger. “Drop your weapons.”

Marcus looked at the daggers in his hands, then at the ring of armed constables. The smart play was surrender. Live to fight another day. But somewhere in the back of his mind, he could hear Scarrow Eck’s voice: “Excessive coin always solves my problems.”

This wasn’t about coin anymore. This was about survival.

“Tell me one thing,” Marcus said, lowering his daggers but not dropping them. “Was any of it real? The planning, the conversation—did any of it mean anything to you?”

Pearl was quiet for a long moment. “I’m good at my job, Marcus. But that doesn’t mean I enjoyed it.”

“That’s something, I suppose.” Marcus smiled grimly. “Give my regards to Eck when you arrest him. Tell him the old ways are dying.”

Before Pearl could respond, Marcus threw himself forward. Not at the constables, but at the narrow gap between two of them. His daggers flashed in the morning light as he fought with the desperate fury of a cornered animal.

He almost made it.

The crossbow bolt took him in the shoulder, spinning him around and sending him crashing into the courtyard wall. As consciousness faded, he heard Pearl’s voice, tinged with something that might have been regret.

“Get him to a healer. And send word to the other teams—the Slink falls today.”

In the rough part of town, where honest folk feared to tread and thieves had ruled from the shadows, the old order was crumbling. But Marcus Holloway, bleeding and broken in a constable’s wagon, knew one truth that Pearl Fraley had yet to learn.

In the darkness between the law and the lawless, something was always waiting to fill the void.

This short story was created by Claude.AI, using the one page dungeon named “The Carriage Heist” in The Rough Part of Town as the training set. This is an experiment to see if the Heartwizard Games roleplaying supplements can be used as source material to generate stories. Hopefully you liked it!