Behind the Scenes | Treasure Island Episode 2

If Episode 1 was about isolation, cold winds, empty inns, and blood on the floorboards, then Episode 2 is the moment the world cracks open. A Crew of Rogues shifts the tone, the pace, and the scope. New characters flood in. New dangers. New temptations. Jim has left the safety (such as it was) of the Admiral Benbow, and now he’s adrift in a city full of shadows, schemes, and charmers with silver tongues.

And so we faced a fresh set of challenges. Let's dive into the behind the scenes of Treasure Island.

The Puzzle

One thing we knew we wanted to fix was the map.

In Stevenson’s original novel, the mutineers’ journey toward the treasure is often clumsy and uncertain — they don’t really know where they’re going half the time. That works in a book aimed at young readers, but it doesn’t fly in a series pitched with HBO-level ambition. We needed the treasure hunt to feel sharper. Smarter. More earned.

So we built in a puzzle.

We introduced something we affectionately called The Dead Man’s Chest, a literal code, tattooed in Roman numerals across Billy Bones’ torso. Jim, having spent time with Billy before his death, is the only one who’s even halfway equipped to decode it. This gave us a chance to tie Jim more directly to the mystery, not just as a witness or a stowaway, but as a necessary player in the quest.

It also let Billy’s ghost echo through the story. Even in death, he's still shaping events, pushing pieces on the board. That mattered to us.

The Conman

The second major challenge? Making Silver work.

Everyone knows he’s going to end up on the crew. Everyone knows he’s dangerous. So the question wasn’t what happens, but how it happens and, more importantly, why Jim would ever trust him.

We had to thread a very fine needle: Silver couldn’t just be charming. He had to be vital. So we asked ourselves, what kind of situation would make Jim need Silver?

We landed on temptation.

Jim's grown up in a sleepy coastal hamlet. Bristol is something else entirely; loud, lawless, full of edges he doesn’t yet know how to navigate. So we gave him a stumble: he’s lured away by a prostitute, distracted just long enough for Black Dog to swipe his bag of guineas. Then the guards arrive. Jim’s in real trouble.

Enter Silver.

He steps in, smooth as you like, returns the money to Trelawney, and gets Jim off the hook. It’s a classic con, but one Jim isn’t equipped to see coming. And in that moment, Silver becomes a savior. A mentor. A rogue with a heart of gold, if only for a scene or two. It’s all carefully engineered, of course, but Jim doesn’t know that. Not yet.

A New World: Behind the scenes of Treasure Island

This episode was also about opening the door wider. The world had to feel suddenly bigger, more layered, more dangerous, more alive. It’s Jim’s first taste of the kind of chaos that’s coming. The kinds of people he’ll have to deal with. The kinds of lies he’ll have to see through.

From the bustling dockside to the murmurs of mutiny already brewing below the surface, A Crew of Rogues is where the game really begins. It sets Silver in motion, gives Jim a glimpse of how far he’s in over his head, and anchors the treasure hunt in something sharper than just “X marks the spot.”

It also lets us have fun with the format; con games, chases, backroom deals. It’s messy, fast, and full of bad decisions. The kind of episode where everybody's lying, and you’re never quite sure who’s playing who.

And that’s exactly the point.

Next Time

We’ll be back with a deep dive into Episode 3: Under a Black Flag and explore how we wrote the mutiny itself - the tipping point where all those careful tensions finally explode.

The OutWrd Team

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