Cherreads

Chapter 23 - The Dragon Gambit (2)

***

White Harbor's shipyards stank of tar and fear.

Castor walked through the drydocks at dawn, and workers scattered like rats. Not running—that would draw attention—but finding sudden urgent tasks elsewhere. Heads down, shoulders hunched, the universal body language of men who wanted to be invisible.

In my old life, I walked through corporate offices and saw the same thing. Different world, same instinct. People know predators when they see them.

The Blood-Red Tide sat in the third dock, hull black and sleek. Master shipwright Harlen stood beside it, back rigid when he saw Castor approaching. The man's hands trembled slightly as he wiped them on his apron—not from cold.

"M-m'lord Bolton." Harlen's voice cracked. He dropped his gaze immediately. "The ship's nearly finished. Exactly as ordered."

Castor said nothing, just studied the vessel. Sixty feet of oak and pine, narrow beam built for speed. Rigging half-complete, deck planking being fitted by carpenters who worked in silence, too afraid to gossip.

The silence stretched. Harlen shifted weight, sweat beading despite the morning chill.

Let him sweat. Anxiety makes men thorough. Though back then the consequences were termination, not flaying.

"Show me below," Castor said finally.

"Yes, m'lord. Of course, m'lord." Harlen practically scrambled up the rope ladder.

The cargo hold was dim, lamp-lit. Harlen's hands shook as he demonstrated the hidden compartment—deck boards lifting on concealed hinges, space beneath for hiding passengers or cargo. The craftsmanship was excellent, seams invisible.

"And the stern compartment?"

"Here, m'lord." Harlen pressed the false wall. It swung open, revealing the narrow space behind. "For valuables. Very secure."

Castor examined both hiding places, running fingers along joints, testing hinges. Harlen watched like a man awaiting judgment, throat bobbing with nervous swallows.

He did good work. But he's seen too much—knows this isn't a normal merchant vessel. In my previous life, this would've meant an NDA and severance package. Here, it means keeping him terrified enough that silence is guaranteed.

"You built this alone?" Castor asked quietly.

"I—yes, m'lord. Well, apprentices helped with basic carpentry, but the hidden work..." Harlen's voice dropped to barely a whisper. "Only me. I swear it. Haven't spoken of it to anyone."

"Good." Castor stepped closer. Harlen flinched. "You'll keep it that way. After we leave, you forget this ship existed."

"Yes, m'lord. Absolutely, m'lord." The man was pale now, understanding the unspoken threat.

Castor handed over a purse heavy with gold. Harlen took it with shaking fingers. "Finish in five days. Bonus if it's four."

"Four days, m'lord. You have my word."

Castor left without responding. Behind him, Harlen sagged against the hull like his strings had been cut.

Outside, wind off the water carried salt and distance. Workers still avoided looking at him directly, finding reasons to study their work intently as he passed.

***

The crew was gathered in a warehouse when Castor arrived—twenty men who fell silent the moment he entered.

Half were White Harbor sailors, hired through intermediaries. The other half were Dreadfort soldiers disguised as crew. They stood in separate groups, tension thick between them.

Jeren stood at the front, arms crossed. He'd changed appearance—beard trimmed, merchant's clothing, but he still moved like a fighter. When Castor entered, Jeren bowed his head in respect.

"M'lord. There's a problem."

"Explain."

"The sailors know half these men aren't real crew. They're asking questions—why a merchant ship needs guards who can barely tie knots."

Of course they noticed. You can't fake competence to people who live by it. I should've anticipated this—same as trying to put marketing executives in engineering roles.

Wrong skillsets show.

Castor walked to the center of the warehouse. Twenty faces watched—some carefully neutral, others showing poorly-hidden nervousness.

He let the silence build. Men shifted. Someone coughed. No one spoke.

"You've been hired for a voyage to the Free Cities," Castor said, voice flat and cold. "Braavos, Pentos, possibly further. Six to twelve moons away from Westeros."

More silence. A few sailors exchanged glances.

"Half of you sail the ship. The other half protect it." Castor's gaze moved across the room, meeting eyes until they dropped. "The Free Cities are dangerous. Pirates, slavers, sellswords. The cargo is valuable. So is your captain. You'll be targets."

One sailor—older, grey-bearded—opened his mouth. Castor's gaze snapped to him. The man closed it again, pale.

"You'll work together. Sailors teach basic rope work, rigging, how to move on deck without looking like fools. Guards teach blade work and boarding defense. By the time you reach Braavos, everyone's cross-trained." Castor paused. "Questions?"

No one spoke.

"You're paid triple standard rates. Gold on departure, gold on return. But—" His voice went colder. "If word spreads in White Harbor about what this ship carries, or who commissioned it, or any detail of this voyage..." He let the sentence hang.

The implied threat was enough. Several men swallowed hard.

"Understood," a few muttered.

"Good. Jeren commands at sea. Disobey him, you answer to me when you return." Castor turned to leave, then paused. "And if any man decides the risk is too high—leave now. No shame. You'll be paid for time served and released."

Nobody moved. Either they wanted the gold badly enough, or they were too afraid of what leaving might imply.

Fear and greed. The two most reliable motivations. Corporate bonuses or feudal gold—the principle stays the same.

Castor left them to Jeren's management.

Outside, he breathed cold air and organized thoughts.

Twenty men who know a Bolton ship is sailing to Essos on unusual business. Twenty potential information leaks.

In my previous life, I'd have made them sign contracts with liquidated damages clauses. Here, the threat of what House Bolton does to loose tongues serves the same purpose. More effective, actually.

If this fails and Jeren doesn't return, those men scatter across the Free Cities and no one in Westeros connects the dots.

If it succeeds... then I decide how many come home with stories.

The calculation was cold, pragmatic. Some would need to stay in Essos permanently—paid off and given new lives elsewhere. The soldiers could return. The sailors would need careful management.

***

Lord Wyman Manderly's summons came that afternoon.

The invitation was polite—dinner at the New Castle, courtesy between Northern lords. But invitations from men like Wyman weren't optional.

He knows something. Wants to probe. This is like those informal lunches where executives fished for information about competitors.

Same game, different trappings.

The New Castle's great hall was sweltering despite winter outside. Fires roared in dual hearths, and Lord Wyman sat like a mountain of green silk at the high table. Food covered the surface—lamprey pie, roasted swan, enough to feed fifty men.

"Lord Bolton!" Wyman's smile was broad, voice jovial. "Come, sit. I hear you've been busy in my shipyards."

Castor sat, accepted wine from a nervous servant. "Commissioning a trading vessel. Expanding Dreadfort commerce."

"The Free Cities?" Wyman forked pie into his mouth, chewing wetly. "Ambitious. Dangerous waters this time of year."

"Manageable risks."

"Hmm." Wyman's eyes gleamed with something that wasn't quite humor. "Most Northern lords leave Essos trade to White Harbor. We have the connections, the infrastructure. Seems odd for a Dreadfort lord to suddenly develop... maritime interests."

"The Dreadfort has resources worth selling. Better profit controlling our own shipping than paying Harbor fees."

"Fair point!" Wyman laughed, belly shaking. But his gaze stayed sharp. "Just surprised a Bolton would trust a bastard smuggler with valuable cargo. Your house has always been... particular about loyalty."

The unspoken question hung heavy: What are you really doing?

Castor met his gaze steadily. "I'm particular about competence. Jeren has both skills and motivation."

"Motivation being gold, I assume?"

"What else motivates men?"

Wyman smiled, but it didn't reach his eyes. "Indeed. Well, I wish your venture success, Lord Bolton. And perhaps—if it proves profitable—we might discuss longer arrangements? Harbor facilities for Bolton ships, reduced fees..."

He wants a piece. Or he wants leverage. Standard corporate partnership overture that's really about control.

"Perhaps," Castor said noncommittally. "After the first voyage proves itself."

"Of course, of course." Wyman gestured at the food. "Eat, drink. You're my guest."

The meal dragged on with small talk and careful probing. Castor gave nothing substantial, deflecting inquiries with vague answers about trade goods and profit margins.

When he finally left, full dark had fallen.

Wyman suspects something unusual. Doesn't know what, but he's too clever to completely believe the merchant story.

Can't stop him asking questions, but I can be gone before he finds answers. Once Jeren sails, Manderly's eyes can't follow across the Narrow Sea.

And if Wyman dug too deep afterward, well—a mysterious trade voyage that never returned was hardly uncommon. Ships were lost in autumn storms all the time.

***

The night before departure, Castor found Jeren on the Blood-Red Tide.

The ship floated at anchor, fully fitted now. Black hull gleamed in moonlight, mast rigging swaying gentle. Water lapped against the docks, and distant city sounds echoed across the harbor.

Jeren stood at the bow, hands on the rail, staring east toward the Narrow Sea via the Shivering Sea. He turned when Castor boarded, and bowed his head in respect.

"M'lord."

"Ready?"

"As I'll ever be." Jeren's voice was steady. "Ship's sound, crew's manageable, supplies loaded. Weather looks fair for crossing."

Castor moved beside him, both men watching moonlight ripple on dark water. Silence stretched comfortable—the silence of men who'd worked together long enough that words weren't always necessary.

This is the moment. After dawn, he's gone for a year.

Maybe more.

Maybe forever.

In my previous life, I delegated constantly. Sent people on business trips, overseas assignments. Never thought twice about it.

Here, sending someone across the Narrow Sea feels different.

More permanent. More final.

Can I trust him completely?

No.

Never trust anyone completely. But I can trust him enough. And building anything requires calculated risks.

"If it goes wrong," Castor said quietly, "you're a rogue merchant. No connection to me. You die clean or disappear."

"I know." Jeren didn't look away from the water. "My family's provided for either way."

"They are."

More silence. Wind whispered through rigging.

"And if I find something unexpected?" Jeren asked. "Intelligence that changes things?"

"Use your judgment. You'll be too far away for ravens to help in time." Castor pulled out a sealed letter, handed it over. "Emergency codes if you need extraction or support. Burn it when memorized."

Jeren pocketed it carefully.

"The girl comes first," Castor said. "Then the eggs. Everything else—including your life—is secondary."

Most men would've flinched at that. Jeren just nodded. "Understood, m'lord."

He accepts it.

Good.

People who understand their expendability paradoxically last longer—they don't take stupid risks thinking they're irreplaceable. Same principle that kept field operatives alive longer than glory-seekers.

Castor clasped his forearm briefly—Northern gesture, respect between men. "Dawn. Don't be late."

"Wouldn't dream of it, m'lord."

Castor left the ship, boots thudding hollow on dock planks. Behind him, the Blood-Red Tide waited dark against darker water.

One year. An entire year where this gambit plays out beyond my control, beyond my sight. In my old life, I hated delegating long-term projects. Always wanted updates, metrics, control.

Here, I have no choice. The distance is too great, communication too slow. I've given him the mission parameters.

While I wait, the gold keeps flowing. The army keeps training. The animal networks keep growing. And across the sea, Jeren hunts a girl who might wake dragons.

Piece by piece.

Layer by layer.

Building something that won't crumble when everything goes to hell.

He walked back through White Harbor's sleeping streets, cold wind carrying the taste of salt and vast distance.

By dawn, the ship would be gone.

And Castor would do what he always did.

Plan. Build. Prepare.

And wait for the pieces to fall into place.

***

CHAPTER END

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