#004 | Raise The Jolly Roger

Jake Shillue
5 Minute Dispatch
Published in
10 min readSep 8, 2018
English privateer Anne Trelawney is tasked with taking down Blackbeard, one of the most feared pirates of all time. With an unlikely group of allies at her side, will she be up to the task?

It was the height of the golden age of piracy. The Marlin was comprised of Captain Anne Trelawney, first mate James Robinson, and a handpicked crew of one hundred able-bodied men. Anne had been commissioned by England to track down the ruthless pirate, Edward Teach, or Blackbeard as he was known.

The Marlin had departed from England three months prior, and made her way down to the Caribbean. Trelawney’s knowledge of naval warfare, matched with the undying respect Robinson had earned amongst the Royal Navy made them a fearsome duo. Trelawney’s usual ship, the Leviathan, was too well-known amongst the pirate underworld and as a result, Anne was given the Marlin for this mission, a newly commissioned warship.

The Marlin stopped in Port Royal, Jamaica. During a recent stop in Florida, Anne and James rendezvoused with a confidant from England. He told the pair that Commodore Duncan Townsend, of Her Majesty’s Royal Service, had sent Nelson Aldrich, an English spy, on a mission to join Blackbeard’s crew by any means necessary. He was instructed to learn the routes of the Queen Anne’s Revenge, Blackbeard’s ship, and relay the information to an undercover English merchant vessel, who would then set up a takedown of Blackbeard. Should Aldrich become compromised, he was to deny any connection to England, and vice-versa.

However, Teach became wise to Aldrich’s intentions and tortured him for three days, before throwing him overboard. By sheer luck, a barrel from a recently sunk ship floated by, and Aldrich held on for two days before he was rescued by a passing fisherman. Rumor had it that Aldrich fled to hide out in Port Royal.

Trelawney and Robinson intended to learn as much as they could from Aldrich, if they could find him. With the boat secure and the men on watch, the two of them went ashore. They entered the first bar they came across, The Rusty Anchor. A dimly lit, yet bustling little shanty, Anne and James scanned the bar. They both locked onto a man seated at the bar, slouched over a pint of ale, his face covered in scars. Robinson and Trelawney approached Aldrich from opposite sides.

“Nelson Aldrich?” Anne asked.

“Nope, you got the wrong guy,” he said, and didn’t take his eyes off his drink.

“I’ve been told you have information,” Trelawney continued, unfazed by his response.

“Unless you’re looking for trouble, walk away,” Aldrich said.

“That isn’t going to work for us.” Robinson said, as he grabbed Nelson by the shoulder to spin him around. As he did, Aldrich grabbed his mug, smashed it into the side of Robinson’s head, and pushed Anne away. He bolted for the door, but barely made it two steps outside before he was met with a swift right hook that caught him across the jaw. Henry Barlow, the ship’s bosun on the Marlin, had been waiting outside in case Aldrich decided to make a run for it.

Anne and James ran outside and saw Nelson lying face up on the ground, out cold, with Henry standing over him with a big, stupid grin on his face.

“Jesus, Henry, I told you to stop him, not lay him out,” Anne said.

“Exactly!” Henry was standing with his hands on his hips, chest puffed out.

James picked up an unconscious Nelson Aldrich and carried him towards the Marlin.

“Let’s go,” Anne started. “Try your best not to knock out any more unsuspecting citizens,” she said pointing at Henry.

After they got some food and drink in him, and had thoroughly convinced Aldrich they were not Blackbeard’s henchmen, Trelawney and Robinson sat the former down with a map of the Caribbean and instructed him to point out the latter’s whereabouts and planned routes.

“According to the original plan, he has spent the last month around Nassau. But in the coming week, the largest treasure fleet in the Spanish Navy will be headed towards Havana, loaded with gold,” Nelson said. “You can be sure that’s where he’s headed next.”

“He intends to take down an entire fleet?” Robinson exclaimed. “He may be Blackbeard, but even Blackbeard can’t take down an entire fleet by himself.”

“Well, Mr. Robinson, that’s cause he’s enlisted the help of Charles Vane and Bartholomew Roberts. All in all? Twenty million Spanish reals will be in that fleet. And if you intend to dance with the devil, you better be prepared to go to hell and back.”

Not only did Trelawney have to contend with Blackbeard, but now she had to worry about Charles Vane and Bartholomew Roberts as well, both master tacticians on the open seas by their own right.

Anne dismissed Nelson from her quarters and kept Robinson, her dear friend and trusted first mate, behind.

“This is a suicide mission, ma’am,” Robinson said. “By himself, Blackbeard is a near unstoppable foe. But with Vane and Roberts…” his voice trailed off.

Anne paced around her desk, arms folded, deep in thought.

“Our only hope is to sail for Tortuga, and pray there is someone who is willing to help. We are facing a juggernaut here and we will need all the firepower we can get.”

Following many drunken nights of discussion in Tortuga, Trelawney and Roberts somehow coerced two captains to accompany them on the trip to take down, “The Devil’s Three,” as they had taken to calling them.

After three days of restocking supplies and filling all three boats with as much armament as possible, the three new comrades left Tortuga and set sail for Havana. The Marlin was flanked by Captain Samuel Morgan of the Intrepid, and Captain William Flint of the Corinthian.

— — — —

With clear skies and a strong wind, Trelawney and company neared Havana in record time. At high noon on the second day, with a stiff wind at their backs and their heading northwest, the lookout on the Marlin shouted, “Four ships, Captain! Two o’clock starboard side!” James Robinson threw a telescope to Captain Trelawney, who fixed the ships in her sights. Four massive Spanish treasure ships. Blackbeard, Vane, and Roberts’ ships were not in sight.

“Full sail!” Anne cried out, and the Intrepid and the Corinthian followed suit, as their sails corralled the wind and throttled towards the Spanish armada. At the center of the armada was the La Luna Azul, The Blue Moon, the largest treasure ship in the world.

As they neared the armada, the lookout on the Intrepid called out a faint outline of a ship on the horizon. Then another, and finally a third. “The Devil’s Three” had arrived. Trelawney gave the call to open the cannon hatches and prepare for battle. Three 30-cannon ships would scare off just about every single pirate on the high seas, but Blackbeard was no ordinary pirate. The Queen Anne’s Revenge alone had 44 cannons, and being flanked by the fearless Charles Vane and “Black Bart” Bartholomew Roberts meant she was virtually unbeatable.

The Marlin, Intrepid, and Corinthian broke formation and moved to form a semi-circle around the enemy. The Marlin beared down on the Queen Anne’s Revenge. Blackbeard appeared to show little concern for the three ships, and understandably so; no sane person would dare attempt direct conflict with him. However, Charles Vane, ever the volatile captain, did not share the same sentiment, and broke off to engage the Corinthian.

Captain Flint gave the order to fire on the Ranger, and the Corinthian unleashed a volley of cannon fire at Vane, with over a dozen cannonballs hitting their mark. Black Bart moved to engage the Intrepid. He charged the Royal Fortune, a massive 40-gun ship, straight at Flint’s broadside. He fired off two shots, one from the long nine gun situated on the bow, and a chain shot round that fractured, but did not cripple, the Intrepid’s mizzen mast.

Trelawney knew she would be hard-pressed to win a direct battle with Blackbeard; she had to get crafty. She handed a dozen incendiary bombs to her men and they climbed up to hide amongst the sails and the crow’s nest. She brought the Marlin around the stern of the ship and aimed the cannons directly at the back of the Queen Anne’s Revenge. On her command, the men rained incendiary bombs down on the Blackbeard’s deck. His crew ducked for cover and abandoned their posts. She gave the order to fire and a dozen cannons opened fire, which splintered the hull and damaged the deck.

The crew on the Marlin cheered in triumph at the hit, and prepared for another pass at Blackbeard’s ship. That spark of excitement was extinguished in a moment, however. Without warning, Blackbeard ordered his men to drop the starboard anchor, which swung the stern of the ship to port side. That slight tactic lined up the Marlin directly in the path of the Queen Anne’s Revenge, at which point, Blackbeard gave the order to open fire. All 40 guns ignited and tore the Marlin to shreds, which eliminated nearly half of Trelawney’s crew, and effectively immobilized the warship.

— — — —

The Corinthian moved to re-engage Vane and his men. Flint steered the ship in close enough for his crew to gain an effective shot not only with cannons, but with rifles as well. The Corinthian and the Ranger were no more than 20 yards apart when both ships opened fire on one another. The firepower left a path of bloodshed and destruction on both captains’ ships. Flint looked around and surveyed the chaos, and tried to regain his bearing. He looked across the deck to see a series of grappling hooks being deployed from the Ranger; they were being boarded.

“To arms, men! To arms!” Flint stood up, drew his sword and shouted as Captain Charles Vane led a boarding party onto the Corinthian.

Vane and Flint engaged in a vicious sword battle, as a bloodbath amongst the two crews developed around them. Pound for pound, Flint was a stronger man, while Vane was the cunning aggressor. Both men clashed swords and landed punches, in a duel for their very lives. In the scuffle, one of Flint’s men bumped into him and threw him off balance. Vane seized his opportunity and sliced clean across Flint’s thighs, and followed it up with a vicious punch to the side of the head, which dropped him to the deck. Just as he was about to deliver the killing blow, a shot rang out and Vane looked down to see blood pooling on his white shirt. He dropped his sword and fell to one knee. He looked up just in time to see Flint drive a sword through his chest. The crew of the Corinthian shouted in victory and continued to thin out the boarding party from the Ranger.

— — — —

The Intrepid and the Royal Fortune continued to circle one another, as the cannons fired away. Both ships had sustained heavy damage, while neither ship gained a clear advantage over the other. Roberts’s ship clearly outmatched Samuel Morgan’s; he very easily could’ve simply outgunned the Intrepid but seemed to be holding back, as if to toy with Morgan.

With a sudden gust of wind, Roberts let down all sail and swung his ship around to directly face the Intrepid and charged, a massive steel battering ram affixed to the bow.

“Open fire!” Morgan shouted to his crew. The men let loose with every gun on board, but the cannonballs seemed to glance off the bow of the Royal Fortune. Roberts slammed his ship into the starboard side of the Intrepid, while his crew unloaded musket fire and fire bombs on Morgan’s crew. The Royal Fortune swung to port side, and unleashed a volley from the cannons, reloaded, and fired again.

Almost nothing was left of the Intrepid. Morgan’s crew had been vanquished at the hands of Black Bart, and a key ally was lost in the battle against “The Devil’s Three.”

— — — —

Anne Trelawney pumped her arms and legs as hard as she could. Her vision was going black, as air seeped from her lungs. With one final push she launched herself above the waterline, and gulped in oxygen. All around her lay the bodies of her crew, including Nelson Aldrich. Her first mate and best friend, James Robinson, was nowhere to be seen. She looked up to see a broken and battered Marlin. The aft sail was crippled, and there appeared to be no movement onboard. She yelled to anyone that could hear her to get back to the ship.

Anne clambered back on to the Marlin, along with a dozen others. She looked up to see the accompanying ships of La Luna Azul had met a similar fate as the Marlin. Blackbeard neared Spain’s flagship and all the treasures she carried.

“Another ship, captain, starboard side” the ship’s bosun, Henry Barlow, called out.

Trelawney raised the telescope to her eye and saw that three ships were sailing headlong towards Blackbeard.

“It’s the Leviathan,” she called out, unable to believe her eyes. She scanned the deck and her eyes landed on Stede Bonnet, an English privateer, looking back at her through his telescope. He tipped his cap towards the Marlin.

It seemed England had realized the mission Trelawney had undertaken, and sent Bonnet down for more firepower. He was accompanied by two other ships, and the trio aimed to create a buffer between Blackbeard and La Luna Azul. The combined firepower from the trio was enough to drive Blackbeard off course.

All of a sudden, James Robinson climbed up the side of the Marlin and collapsed on the deck, spitting up water.

Trelawney pulled her friend to his feet and shouted to the crew to swing the ship to port side; they still had enough control over the boat for one more volley of cannon fire.

With the cannons fully loaded, the Marlin sent a volley of cannon fire exploding out of her, delivering a perfect broadside hit on Blackbeard’s ship. With the combined firepower from the Leviathan, the Corinthian, and the two new ships, Blackbeard and his crew were soon overtaken. Bartholomew Roberts, who sensed the unwinnable situation, turned tail and fled for Nassau. The La Luna Azul escaped with only minor damage done, and continued on for Havana.

Bonnet picked up Trelawney and the remaining crew on the Marlin, and welcomed them aboard the Leviathan.

“Looks like we got here just in time,” Bonnet said, as he eyed the damaged ships strewn about the ocean.

“We knew what was ahead of us when we took on this mission,” Anne said, solemnly.

“Well Captain Trelawney, I believe this is your ship and this,” Bonnet said as he pointed to a handcuffed Blackbeard, “is your prisoner.”

Anne walked over to Blackbeard and knelt down, looking him dead in the eye.

“Well, Mr. Teach. Looks like you and I have some place to be,” Anne said.

With that, Trelawney threw Blackbeard in the brig, and set sail for England. They were bruised and bloodied, but they had their prize.

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Jake Shillue
5 Minute Dispatch

Founder of 42Seventy | Author of 5-Minute Dispatch | Storyteller by trade and traveler by nature