Lefty, the Pirate

Boatswain of the Sea Wyvern, Faithful Cohort to the Gang of Five


“Arr! Save a little for Lefty, Chairman!”

Description: “Lefty” was introduced to the Gang of Five as a conscript pirate under the banner of the Crimson Fleet, lead by “Slipknot” Peet. The severely beaten Lefty – so called because his right hand has been replaced by a hook – looked the part of a pirate, with his scraggly beard, tanned skin, and a wiry frame. He inconsistently wore an eyepatch and frequently switched the eye it covered. Lean and lanky, Lefty was known for equal parts cowardice and bravery, frequently entering combat through a ceaseless string of “SHITSHITSHITSHITSHITSHITSHITSHIT!” While not dapper, per se, Lefty cut a classic figure in his pirate garb. Affable, friendly, and almost comically timid, Lefty was frequently seen as the group’s comic relief, a man for whom adventuring most certainly found him.

The Abyss, however, breaks boys and makes men, and as boatswain of the Sea Wyvern, Lefty has become a good deal tougher and less foppish than he was when he first met his friends. His demeanor is that of the ideal sidekick: willing to offer comic relief at times, steadfast and loyal, competent, and fearless. While in the Abyss, Lefty regained the presence of his missing right hand, thanks to Lirith, and while he revealed that his real name was ‘Virgil’, to those who know him best he’ll always be ‘Lefty’.


Biography: Lefty was one of Slipknot Peet’s men, nominally, and one of the pirates engaged in the sacking of Farshore when the group at last arrived. Attempting to get one over on the Fleet, Peet ordered his ragtag group of pirates to sack and burn Farshore in order to loot it before the Fleet arrived. Lefty alone survived the raid, being taken as prisoner, and helpfully volunteered knowledge of the Fleet’s plans to attack Farshore after the party spoke to him and plied him with promises of clemency for his crimes. In order to prove himself, the Gang of Five provisionally took Lefty on as a sort of valet in their travels about the isle. A competent sailor and fighter, Lefty lacks much in terms of magical ability, and it was almost out of enjoyment of his company alone that Dorian decided to take the pirate on as his personal cohort.

Lefty proved invaluable in recovering and repairing the Sea Wyvern, and showed his steel as a trustworthy and steadfast ally to the group, following them – against the promptings of his spirit – to Golismorga and Thanaclan. Completely foregoing Peet and the fleet at large, Lefty eventually told his story in part, stating that he had served as a deck hand on various pirate vessels for years, starting back when he was a boy with no skills and just an ample love of the sea. His vessel, a privateer ship bound for the west, was boarded and claimed as booty by Peet on behalf of the Crimson Fleet, and Lefty was permitted to live after swearing fealty to the fleet. From there on, Lefty occupied the role of abused mascot of the crew at Rat’s End, Peet’s base, until being dragged along for the raid on Farshore, where he was captured.

On his trips to Sasserine, Lefty tended to spend all his time at The Golden Hind, the casino and bordello owned by Moxie, guild leader of the Black Roses. It was here that Lefty began something more than business and something less than a relationship with Zelda, the madame of the house, a relationship which, to hear it from him, has blossomed into actual love.

Almost always good for a laugh, Lefty’s darkest hour nevertheless came when the group resolved to travel to Scuttlecove to rescue the kidnapped Lavinia. Holing up in the hold of the Hellfish, the party’s skiff claimed from the Rat’s End raiders, Lefty drank himself stupid for nearly two straight weeks in the hopes he wouldn’t have to think about the coming voyage. It was apparent something was drastically wrong.

After being magically forced into sobriety and pressed by his friends, Lefty at last admitted the truth: Scuttlecove was known well to him, and due to certain ugly dealings there, it was a place he hoped never to return. Eventually he was persuaded to make the trip with the promise that he would remain disguised and safe, but shortly after their arrival, it became apparent that Scuttlecove had not forgotten Lefty, either.

Years prior, Lefty’s travels had taken him to Scuttlecove. Believing it to be the fabled “pirate’s paradise” he’d heard about, what he instead found was a cuththroat, salt-caked hell that threatened to end his life with every day he spent there. Desperate to leave, he accepted a job given to him by Scuttlecove’s most powerful drug pusher, a wizard named Kedward Bone. Tasked with ensuring the safety of a supply of drugs worth tens of thousands of gold, Lefty steered a tiny raft loaded with cargo through the treacherous waters of the cove, and failed. The sea claimed the freight, and Kedward, for Lefty’s failure, claimed his life, putting him on “the Hooks” at the Plaza of Hanging Ruin.

It’s here that Lefty’s story would have ended, had he not, in his delirious and weakened state, been rescued by “a beautiful woman with black angel wings”. After resting up to regain his strength, Lefty took the risk of stowing away on a vessel bound for Sasserine, and it’s there, on that vessel five years prior, that he had been shanghaied by Peet and taken into the Crimson Fleet.

As it happens, Lefty was right to be nervous to be back in Scuttlecove. He’d been in the city for hardly a few hours when agents of Kedward Bone approached him and told him to visit the gangster’s tower, lest he be killed in the streets. Reluctantly, Lefty agreed, and tried to visit alone, though he was stopped by his friends, who swore that his burdens would be theirs. Kedward Bone, rather than seek vengeance on the man who escaped his punishment, saw in the group an opportunity to resolve a problem that had been bothering him: in exchange for Lefty’s debt, the party would infiltrate the Porphyry House brothel and rid him of an up-and-coming competitor in the Scuttlecove drug trade.

During the course of the next few nights, the party cracked the case and managed to stop the production of a potent and demonic narcotic. It was further revealed that Lefty’s savior, the black-winged angel, was a woman named Tyralandi, a half-succubus, half-nymph who orchestrated the downfall of the brothel’s drug pushers from within. Lefty, near mental collapse, asked why she had saved him all those years ago, and was given a cryptic response from the demon, who alluded that not only was she aware of the events that would transpire that day and that her rescuing him from the Hooks was to prepare for that, but that on an even larger game board, Lefty had been saved, had worked for Kedward Bone, had come to Scuttlecove, and had began sailing in the first place all in keeping with some grand plan that he was not to be privy to, and even more unsettling, that the grand plan Lefty’s entire life was orchestrated to serve was implemented solely so that Lefty would end up with the Gang of Five, and serve an important function within their ranks. It was a deeply unsettling thought with terrifying implications for everyone involved.

As the sun set on Farshore and the group prepared to set sail for the Abyss, Dorian offered Lefty the opportunity to remain behind, and perhaps start a life with his lady love.

Proving that he has no quality so great as his loyalty, and proving that loyalty greater than most men capable, Lefty gritted his jaw and told Dorian he would follow him even to hell.

While Lefty has formally retired from combat duty as Dorian’s cohort, he captained the Sea Wyvern through the waters of the Abyss itself, caring for the boat while the Gang of Five was on land and, in a surprising turn, leading the defense of the ship and her crew with competence, determination, and most of all, courage.

As the Sea Wyvern and her crew returned to the Prime, Lefty exalted in their collective victory and sailed them to Farshore, and then returned with the other members of the Gang of Five to Sasserine, where he was reunited with his lover, Zelda. Perhaps taken by the moment, Moxie, Zelda’s guild mistress and employer, encouraged the woman to seek her happiness with Lefty should that be what she wanted, and equally ecstatic, Zelda took her boss up on the offer, becoming a permanent resident of the Sea Wyvern alongside her man.

Leaving the Abyss was the last thing Lefty needed to have a perfect life. And now that he has, Lefty finds himself in the enviable position of having exactly what he wanted from the time he was a little boy: he sails the open seas, cares for a magnificent ship, travels the world, and spends his time in the company of his closest friends and the woman he loves.

Lefty, the Pirate

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