Pyrate: Black Flag

2024 Young Or Golden Writer
Manuscript Type
Logline or Premise
Tagged with killing a Spanish Viceroy and the heist of King Philip’s doubloons, Captain Connachan learns of an imminent Spanish invasion of her base on Isla Tortuga. She’s compelled to marshal precious resources and rally detested rival pyrates, including her archenemy, to defend their rebel island.
First 10 Pages

Author’s Note

This is the fourth novel in my Pyrate Series. If it’s the first one you’ve picked up to read, you may be wanting more backstory, to put the players and events in context. Unfortunately, doing that would drag out the pace of this novel for those who’ve already read the previous three. As a result, I’ve consciously attempted to minimize filling in the backstory. But…you can always buy the first three novels to catch up.

“If you must look back, do so forgivingly…”

Maya Angelou


…The jagged rocks rose behind crashing water and exploding mist, as if cast out by the demons of the Caribbean Sea. They disappeared with the water’s rush, then reemerged as inanimate soldiers threatening to rip open a ship’s hull and let the waves toss ashore the remnants of its carcass.

“The Spanish call it Isla del Diablo,” shouted Master’s Mate Drago above the howling wind and thundering waves. “A sailor’s worst nightmare.” I did not need his explanation.

With Pandora’s sails trimmed and anchors at the ready, our crew looked on in anxious silence, mesmerized by the deathly images. I could see it in their eyes—the sense that Captain Garret Connachan had lost her mind. Even I questioned her sensibility.

“Steady as she goes,” Garret bellowed above the clamor.

“Mother of Satan,” Drago swore.

Pandora continued on, bearing lethal cargo we sought to unload—cargo of the most vile form.

- Kat’s log book 17 May 1601


The hulking, dark-skinned pyrate sat knees-bent amid the damp stench of the cargo-hold, where water beaded and dripped like a ship’s sweat. Pandora’s extreme pitch and roll caused his rusting shackles to etch bloody furrows on his wrists and ankles. The wrist-manacles did the most damage, not having been designed for a man with such massive forearms. Yauggan De Graaf didn’t notice the sting. His body already bore the scars of a man who devoured pain for a living. His Black half softened the visual impact of the ghastly wounds that his Dutch half would have emphasized.

“Damn varmint!” he swore at the oversized rat who took a piece of him. He kicked and missed as it retreated.

De Graaf expected a merciless fate at the hands of Captain Connachan. She’d proven herself to be the witch he’d always sensed she was.

Despite the presence onboard of a known executioner—the behemoth Musa—De Graaf doubted beheading was the Witch’s preference. ‘Too quick a death,’ he thought. Connachan would want him to suffer at length. Being thrown overboard in chains would yield a slower, more miserable death. Still, there was only momentary exhibition in that. Hanging was more likely. Besides taking longer, it offered the spectacle of a jerking body and the shame of defecation.

The worst possibility, he thought, was keelhauling—scraping his body around and under the ship’s hull. He himself had once meted out that punishment. But he doubted Connachan had the stomach for watching a slab of bloody flesh and organs drip all over Pandora’s deck at the finish. That sight had left many of his own hardened crew retching out their innards.

‘Whatever she chooses,’ De Graaf thought, ‘I shall die with honor.’…just as the most feared pyrate in the Caribbean should. Having burned brightly, being snuffed out within minutes seemed far better than growing old, dissolving like a crumbled ember in a wasting fire.


The architecture and vivid colors of Cartageña never failed to enchant first-time visitors to Spain’s Caribbean jewel. But in this moment, there was no charm in Governor Acuña’s opulent office. He and General Serezo stood on either side of the long, gold-embossed ebony table where the two men had often planned activities requiring military support, including construction of the city’s fortress wall, various military installations, and even the Governor’s still-unfinished palace.

Despite their past collaborations, Governor Acuña was now furious with Serezo. Together, they’d planned the exchange of doubloons for Viceroy Valdez, a close friend of now-deceased King Philip II. Valdez was said to have been kidnapped by an English pyrate known as The Witch. General Serezo had assured the Governor his men would secure the Viceroy’s safe return. But now here he was, delivering news of abject failure—the loss of the doubloons and drowning of the Viceroy. That news threatened Governor Acuña’s recall by the current King—Philip III. Acuña’s dreams of his new palace were dissolving into the nightmare of a walled prison cell.

“I gave you complete control and unlimited resources, General,” he screamed. “Only sheer incompetence could have produced such a result.” His spittle showered between them, falling harmlessly on the tabletop.

Serezo remained stone-faced and stone-bodied, offering no defense. Acuña sensed the General had expected his anger.

The Governor sat, looking away and pondering his next steps. There was no reversing the damage. Although Connachan, the English pyrate, bore primary responsibility, he also needed a scapegoat on his own side. It couldn’t be Serezo; that would not sit well with the military.

He thought to blame someone who’d participated in the abortive exchange and perished in the effort…thereby unable to mount a defense. The best alternative was Felipe De Heredia y Ortega, a wealthy and prominent financier in Cartageña. The Viceroy’s captors had reached out to Ortega for aid in transmitting their ransom request to King Philip. Ortega had no defenders; most merchants in the city resented his frequently besting them in their business dealings. The man would be perfect to take the fall. Nonetheless, General Serezo required suitable punishment—perhaps a short imprisonment. He was confident Serezo would accept that since he ultimately needed the Governor on his side if he were to continue in his current role.

Finally, Acuña rose. “Guards,” he called. Two soldiers entered momentarily. “Escort the General to the penitenciario. He is to be held there pending further word from me.”

Serezo unsheathed his cutlass with his left hand, offering it up to Acuña pommel first. “As you wish, Governor. I shall await your call.” He bowed before turning to exit with the guards.

As the men left, Acuña sat back down, knowing that the most difficult news to deliver to King Philip III would be the Viceroy’s drowning rather than the loss of the doubloons. He needed to flesh out the narrative pointing to Ortega’s fault in the failed exchange…and the primary participation of the English pyrate—Connachan.


‘No one in his right mind would choose to land on this God-forsaken island,’ I thought, glancing at the disjointed remains of a few skeletons lingering on the shore. They were likely to be De Graaf’s only form of human companionship while living out his remaining days here.

William and I stood next to Garret, flanked by six other crew members, all with pistols drawn and aimed in De Graaf’s direction. Others of our crew finished unloading a barrel of water, some food supplies, a knife, an empty pistol, gunpowder, a long-coat, a sheet of canvas and a variety of small tools. One of them dropped a roped canvas bag containing pistol balls some fifty yards away, near the far end of the narrow, pebble-strewn beach.

Garret pointed her pistol toward De Graaf’s feet. “You shall make your final peace here,” she yelled above the pounding surf. “Fair punishment for brutally slaying Viceroy Valdez.”

“That bastard was still alive when I left him,” De Graaf shouted back.

“His death was imminent,” Garret countered.

“So you claim.” De Graaf directed a wad of spit her way.

De Graaf couldn’t have known Garret had been forced to take Valdez’ life herself, to end his misery. She’d earlier confided to me that she wanted this virtual killer of her former lover to suffer a long, lonely existence on this isolated speck of land, enduring maximum pain—both physical and mental.

“This place is the Devil’s hunting ground,” she shouted to De Graaf. “You shall meet him here in good time, but not before daily regretting your actions.”

“God damn you…and all your ancestors, Witch!” he replied

“God is not at your calling,” she yelled back. “He will have no mercy on your rotting soul.”

De Graaf looked around, taking in the foreboding sights of this miserable island. His reality seemed to be setting in. “My men shall not take kindly to your actions here,” he said. “I can already see them ravaging you like rabid wolves craving female flesh.”

William drew his cutlass quickly and stepped forward, as if to slice a few more scars on De Graaf’s corpus…soon-to-be corpse.

“No,” shouted Garret, extending her arm. “Leave him be. He is not deserving of a quick release.”

William hesitated before resheathing his sword. I think he took De Graaf’s words personally, because he fancies Garret.

De Graaf taunted him, “You are a sorry want of a man.”

William could not constrain himself. He redrew his sword and darted toward De Graaf. But Garret jabbed out her leg, tripping him. He fell forward, scraping on the pebbles. De Graaf roared with laughter.

William rose, glaring back at Garret. “Damn you.”

“Stand down, William. This is not your call.” Garret turned to walk away. De Graaf laughed in his gravelly voice, spitting in William’s direction. William returned the spit and turned to follow Garret. The others backed up, keeping their pistols pointed at De Graaf.

“Shoot me,” De Graaf challenged. “Shoot me now.”

No one did. But then he took an aggressive step toward us. Three pistols fired nervously. Two shots whizzed past him. The third bit the top of his shoulder. He stumbled momentarily but grinned in defiance. “You are all cowards,” he bellowed.

I and others continued walking backward, training our pistols on the wounded beast. He shouted once more at Garret, “You shall regret this, Witch. Be certain of that.”

One of our men fired a warning shot in the air as we proceeded to the longboat. De Graaf threw up his right fist. “Damn you all, you bastards. When I get off this island, you are all dead men,” he excalimed. Despite the circumstances, his words sent chills up my spine.

- Kat’s Logbook

William trailed Garret as they neared the longboat. “You realize there is no assurance De Graaf will die here,” he grumbled.

Garret stopped and turned to face him. “Leave it be, William. The deed is done. God will have his way with the beast.” She turned back and continued walking.

After several paces, William continued, “I do worry about his crew. We can expect them to react with force.”

“They won’t even know what has become of him,” replied Garret, “or that we played a role in his disappearance. His only men who witnessed our ambush were with him at the time. And they’re all gone…as far as we know.”

“Except the Jew.”

“I trust Yosel implicitly. It was he who first informed me of De Graaf’s scheme.”

“Which makes him a traitor to his former captain. Who is to say he will not betray us?”

“Leave it be, William.”

“You realize you are assuming there was no one from his campsite who may have remained behind in the jungle, observing our ambush.”

Garret paused. It was a fair point. “Perhaps careful vigilance on Tortuga is in order.”

William accepted her concession and altered course, “I am anxious to be back there…mostly for the food.”

Garret nodded. “I, too, am famished.” She stopped for a moment and leaned in close, whispering in his ear to avoid being overheard, “Before we get there, we must settle on the distribution of the King’s doubloons among the crew.”

“And where to secure our own,” William whispered back. They shared a common concern…Pandora was not the ideal location to hide their portion of King Philip’s doubloons. “No doubt we shall need them when the English Navy comes after us for firing on the Mercilus. Or worse yet, the Spanish Navy.”


De Graaf sat on the pebbled shore, pressing his hand hard against his shoulder to stem the bleeding. “Damn that witch,” he mumbled.

He thought back to the night of his assault on Pandora, in an effort to capture Viceroy Valdez from Connachan and kill her to boot. She’d just confirmed Valdez died in the process. But at least he’d escaped with the Viceroy’s ear and ring, to convince the King Valdez was still alive. It prompted Philip III to send forty thousand doubloons for his release. First Mate Stevens, posing as the Viceroy, had drowned during the exchange. Still, his pyrates had secured the coins, which Connachan had then stolen in an ambush…no doubt relying on information from one of his own men. ‘If I ever get off this damned island,’ he thought, ‘I will rain bloody hell on the Witch, her partner Tovery, and the traitor in my own crew.’


“Buenos dias su excelencia.” As Tesorero Sanchez was saying it, Governor Acuña pointed to a chair.

“Thank you for coming, Tesorero.” Acuña drew back the chair behind his polished Brazilian hardwood desk—one free of clutter, aside from a folded parchment. He sat. “I presume you know why I summoned you.”

“I imagine to share news of the exchange. I trust it went well.”

“I am afraid not. Not at all.” Acuña looked down at the parchment while his aide poured French port into each of their silver goblets. “Only General Serezo has survived. He informed me that the Viceroy’s captors initiated fire, which his men then returned. The Viceroy jumped overboard in the ensuing chaos. The General entered the water to save him but was unsuccessful. He then watched as the pyrates slayed everyone in the boat and took the doubloons.” He reached for his goblet. “Tis an unmitigated disaster,” he lamented, before sipping his port.

Sanchez sipped from his own goblet, his thoughts immediately turning to his good friend, Yosel. Not wishing to risk the Tesorero’s life by having him participate in the exchange, the Governor had insisted Yosel take his place as official bearer of the doubloons. Though Yosel was a relative newcomer to Cartagena, Sanchez’ friendship with him was fast forged by their common love for the wizardry of numbers. The Jew intended to establish a trading business in this bustling city. He’d invited Sanchez to partner with him in that endeavor, suggesting it would be an excellent way for the Tesorero to dip into the flow of capital coursing through Cartageña like molten gold floodwaters. Concern for his would-be partner forced a question, “What news of Yosel, the Jew?”

“The General said he was among the first to exit the boat. That was the last he saw of him.”

Sanchez shook his head, imagining Yosel had drowned. ‘Most unfortunate,’ he thought. ‘He was a good man; he deserved better.’

Governor Acuña continued his summary of the events, “Señor Ortega was shot in the face by the lead pyrate.”

Sanchez knew Ortega as the foremost financier and deal maker in Cartageña. No commerce occurred in the city without his being at the dark center of it. As the primary middleman between the pyrates and King Philip, Ortega had accompanied General Serezo to assure the pyrates the exchange would be uncontested.

“One odd item about that,” Acuña added. “The General tells me that, just before he was shot, Señor Ortega smiled at his killer…as though they were friends. If so, that would confirm my suspicion that Ortega was more than a mere messenger; he may well have been the mastermind of the ransom scheme.”

Sanchez was wide-eyed.

Governor Acuña went on, “I believe we must take General Serezo’s observation as credible. I am therefore authorizing you to seize control of Ortega’s residence, financial affairs and assets…at least until we can determine the man’s guilt or innocence.”

“I shall inform the bank and serve notice to the merchant community that any open transactions with Señor Ortega must henceforth flow through me,” Sanchez nodded, “…as your representative, of course.”

“We must also have someone investigate whatever evidence may be available.”

“Someone deeply familiar with financial matters,” specified Sanchez. He sipped his port and returned his goblet to the desk. “Were Yosel still with us, he would be my recommendation. Let me give the matter further thought.”

“Just so, Tesorero. Please keep me informed.” Acuña paused. “If you do find something in Señor Ortega’s dealings that may point to his guilt in this matter, I shall expect you to let me know immediately. In person, if you please.”

“Of course, Your Excellency.”

The Governor rose from his chair. “Thank you for coming. I must now attend to the rather sad task of composing my message to King Philip. He will not be pleased.”

Sanchez left Governor Acuna’s residence with mixed emotions—honored to be asked to oversee Señor Ortega’s affairs but saddened by the likelihood that his friend Yosel was no longer among the living. He had no idea Yosel had been rescued by De Graaf and his men following their encounter with the Governor’s boat. More importantly, he was unaware of just how intricate Yosel’s network was. Secretly a member of De Graaf’s crew, he was also the pyrate’s personal counsel regarding the ransom scheme. What’s more, the Jew had been Garret Connachan’s informant, in return for her having previously saved his life. The man was a virtual treasure chest of surprises.

Following Sanchez’ departure, Governor Acuña picked up the folded parchment on his desk…from King Philip. He opened it once again, hoping he’d misread the King’s message the first time around. He hadn’t.


Reid Linney Sat, 03/02/2024 - 19:50

Since this novel is a continuation of my already-published trilogy, some of the content in the first 3,000 words is intended to provide context from the previous novels, all three of which were named Page Turner Award Writing Finalists in prior years--Pyrate Rising, Pirate Assassin and Pyrate Crossover. The last of these three was longlisted. I'm submitting the trilogy separately for the Book Award in the Series subcategory.

I should also point out that my chosen spelling, P-Y-R-A-T-E, is the original English spelling of the word.

Finally, my selected pen name for this series is Reidr Daniels. 'Reidr' was a nickname given to me by friends at a very young age. 'Daniels' pays homage to my grandfather, a WWI veteran of the British Army.

Thanks for your time and consideration. It's much appreciated.