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Behind the Scenes: Treasure Island Episode 5

Pirates run through a dark jungle with swords and lanterns. Text reads "Treasure Island, New Episodes Every Monday." Moody and intense.

Episode 5 of Treasure Island, The Devil’s Apprentice, marks a pivotal turning point in Jim Hawkins’ journey — not just as a character, but as a young man being shaped by a world far darker than he anticipated. This is the episode where he learns to survive not by clinging to morality, but by adapting to the ruthless logic of the men around him. And the man closest to him now is Long John Silver.


Apprenticed to a Pirate


In this chapter, Jim falls under Silver’s wing. Under Silver’s tutelage, Jim learns how to shoot and how to fight with a sword. But the lessons go far beyond combat. Jim is forced to witness the cruelty and chaos of the mutineers up close, seeing acts of violence and betrayal that are far removed from the boyish adventures he once dreamed of.


Yet somehow, he holds his nerve. Why? Because of Livesey. His promise to rescue Jim, whispered across enemy lines, becomes a kind of lifeline - the one thread of hope that allows Jim to maintain a sense of self while walking among monsters.


Behind the Scenes: Staying Faithful to Stevenson ...


While we took creative liberties in this episode, many key elements remain rooted in Stevenson’s original Treasure Island. Livesey and Ben Gunn working together to regain control of the stockade and outmaneuver the mutineers is pure classic adventure storytelling. Their calculated plan, using Morgan as a wedge to divide Silver’s crew, plays out with familiar beats, but with new consequences. Morgan’s eventual takeover of the mutineers, wresting control from Silver, mirrors the idea that in a world run by pirates, power is temporary and betrayal is currency.


... and Breaking Away


Back view of a woman in period clothing with raindrops, overlaid text "THE DEVIL'S APPRENTICE V" and "TREASURE ISLAND," OUTWRD logo.

One of the boldest additions in this episode is the flash forward, a window into what happens after the island. We learn that Captain Smollett was dishonourably discharged from the Navy, and that Jim himself was arrested. The twist? His arrest comes as a result of Eliza and Hunter striking a deal with the Crown.


In an earlier draft, Eliza didn’t live that long, originally killed by Morgan at the end of episode two. That version cast her death as a warning for Jim, a reminder of the price of disobedience. But as the story evolved, it became clear Eliza still had a role to play. Her survival gave us an opportunity to explore an alternative path — someone who could replace Jim in the eyes of the authorities. She had spent as much time with Billy Bones as Jim had, and thus knew everything he did - including the coordinates to the island. With Hunter’s knowledge to complete the puzzle, the Crown no longer needed Jim… or Trelawney. Both were discarded, their reputations burned.


To enrich the island’s atmosphere, we introduced a small but important addition: Flint’s decaying cabin. It serves as more than a mere relic, it’s a suggestion that this place once meant something. It wasn’t just where Flint hid his treasure; it was where he lived. In doing so, we started to build a kind of spectral lineage — the sense that these pirates didn’t just bury gold here; they buried their pasts. The weight of history clings to the island, even as new blood spills on its soil.


Bargaining with the Devil


At its heart, this episode is about Jim making a deal with the Devil, or at least, with the Devil he knows. Silver becomes a guide and a threat, a father figure and a tormentor. By aligning with Silver, Jim survives. But survival comes with a cost: when he finally returns home, he’s punished not by pirates, but by the people who were supposed to protect him.


Silver’s world may be ruthless, but at least it’s honest. The world of the Crown is far more duplicitous and ready to discard Jim the moment he becomes inconvenient.


Who Survives?


If you’ve been paying attention, you’ll have noticed that some familiar names are conspicuously absent in the present-day segments. This is deliberate. Each episode functions like a puzzle, inviting you to play detective. Who made it off the island? Who didn’t? What alliances fractured, and who paid the ultimate price?

As Treasure Island barrels toward its climax, that growing sense of dread will only deepen.


In our next behind the scenes blog, we’ll be diving into Episode 6: Dogs and Murderers, where Silver’s manipulations grow more complex and Jim’s loyalty to the pirate begins to come at a higher price. Stay tuned — the waters are getting bloodier.


The OutWrd Team

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Listen to Treasure Island on OutWrd+ and get access to other projects like Broderick: Murder on the Amalfi Coast, At the Crossing and more.

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