After an attack on the ship he was aboard, Edward found himself stranded on a deserted island with an Assassin.
- Crewman: Hold fast! She's on us!
- Edward: Can you see her?
Edward looked at the ship and saw an Assassin casually walking on the ledge of the ship.
- Edward: Man the cannons!
- Bramah: Our helmsman's dead! Someone take the wheel! Kenway! Take the bloody wheel!
Edward took the wheel and attacked the enemy ships.
- Bramah: Uncork the cannons, lad!
Unload all the shot we have!
Fire on those bastards!
We'll give a good broadside. Ready!
A lightning strike struck the ship, and made it vulnerable.
- Bramah: Bring us in close, Kenway! We can scuttle her!
Edward got in close to the ship, and sank the HMS Intrigue.
As the crew were celebrating, the magazine was lighting on fire.
- Crewman: The magazine! It's going up!
- Bramah: Douse the flames! Get in there, you mongrel!
The Assassin appeared and air assassinated Captain Abel Bramah, with Edward the only one seeing him, stare down. However, Edward and the Assassin were blown overboard by the magazine explosion, to which Edward fell into unconsciousness. The memory turned several years back.
- Caroline: Is it dangerous? Edward?
- Edward: Hm?
- Caroline: Privateering. Is it dangerous?
- Edward: Wouldn't pay so nice if it weren't.
- Caroline: Why not sail with the king's navy? Earn a proper wage. Sail under gentlemen.
- Edward: Sod the navy's gentlemen. For every shilling I'd earn, the captain'd get six hundred. That's no way to earn a fortune.
- Caroline: We don't need a fortune.
- Edward: It's not about need, Caroline. I want food that don't make me sick. I want walls that hold back the wind. I want a decent life.
- Caroline: H-how long would you be gone with these privateers?
- Edward: A year, I reckon. Two at the most.
- Caroline: All right. No more than two... promise me...
Edward woke up in the water in the present and swam towards a beach, where the Assassin followed him, injured.
- Edward: Was it good for you as well?
- Walpole: Havana... I must get to Havana.
- Edward: Well, I'll just build us another ship, will I?
- Walpole: I can pay you. Isn't that the sound you pirates like best? One hundred escudos.
- Edward: Keep talking.
- Walpole: Will you or won't you?!
- Edward: You don't have that gold on you now, do you?
- Walpole: Bloody fucking pirates!
The man attempted to shoot Edward with a flintlock pistol, but failed as the gunpowder was wet.
- Edward: I am on to you, sneaksby!
The man ran off into the jungle, and Edward gave chase.
- Edward: Come on, mate! We're off to a bad start!
It's a hundred leagues or more to Havana! Will you walk that distance?
- Edward: Posh git. Where's he running to?
- Walpole: Follow and I'll kill you!
- Edward: We could work together on this!
- Walpole: Keep your distance!
- Letter: (Mr. Duncan Walpole). I accept your most generous offer, and await your arrival with eagerness. If you truly possess the information we desire, we have the means to reward you handsomely. Though I would not know your face by sight, I believe I can recognize the costume made infamous by your secret order. Therefore, come to Havana in haste... And trust that you shall be welcomed as a brother. (Your most humble servant, Governor Laureano Torres y Ayala.)
Edward donned Walpole's robes.
- Edward: Mr. Walpole... let's collect your reward.
Edward heard shots in the distance, and proceeded to investigate, leading him to a ship.
- Edward: That schooner'll do me just fine...
- Soldier 1: The Commodore's gone ahead to Kingston. We're to commandeer this lubber's ship and follow.
- Bonnet: S-sorry, uh, Kingston? No, no... our destination is Havana. I'm just a merchant–
- Soldier 2: Quiet, you bleedin' pirate! You'll hang for the mess you made out there.
- Bonnet: Sir, I had nothing to do with this attack. My crew and I had merely anchored to water and resupply!
Some of the crewmen attempted to escape.
- Soldier 1: Hold it! Stop them!
The crewmen were shot by soldiers.
- Soldier 1: Give me one reason I shouldn't vent your skull.
- Bonnet: Take my sugar! Take anything you like!
I'll pay you! Anything you like!
Oh God. Oooooh God!
Edward killed the British soldiers and rescued Stede Bonnet.
- Bonnet: By God's grace, sir, you saved me. A profusion of thanks!
- Edward: Is that yours?
- Bonnet: It is my vessel, yes. But, ah... here lies its poor captain. And I have no art for sailing.
- Edward: I can pilot her myself. No mind.
- Bonnet: You don't mean to abscond with my ship, do you?
- Edward: I'm Duncan. What's your name, friend?
- Bonnet: Stede. Stede Bonnet.
- Edward: Well Mister Bonnet, let this stay 'twixt us... but I am on a secret errand for His Majesty the King, God save him, and I must get to Havana with speed.
- Bonnet: Ah... that is a relief, sir. Havana is also my destination. Our ways lie together!
- Edward: Natural allies then.
- Bonnet: Oh, you put me at ease, sir. To think I took you for a pirate when you first appeared.
- Edward: Did you?
- Bonnet: Yes! You have an... uncommon way of handling yourself. Quick and easy, if I may say. Gave me quite a fright! But all things considered, I think it's turned out to be a rather fortuitous day, hasn't it?
Edward started swimming towards the ship.
- Bonnet: Lacking a rowboat, I'm afraid we'll have to swim to my ship.
- Edward: Hardly the worst thing to happen.
- Bonnet: Oh... Oh, this is difficult. I should have taken the coat off!
Edward took the wheel of the ship.
- Bonnet: Welcome aboard, Duncan. She's a modest schooner but well-suited to my purpose. Trafficking cargo from my plantation and such.
- Edward: She'll do fine. There's a strong wind now. Let's strike to full, shall we?
- Bonnet: Ah, there's a tug of the wind at my hair! I find a bracing comfort in the feel and smell of the ocean. The raw stink of... of possibility!
- Edward: That's a top way of seeing it, mate.
Edward sailed out of the bay.
- Bonnet: We've really opened it up now, haven't we! Those sailors were quite animated by the idea of pirates roaming these waters. Is it a real danger, do you suppose?
- Edward: A possibility. But most pirates stalk the windward passage between Cuba and Hispaniola.
- Bonnet: Oh, I see. Yes, that is a bustling strait. But I shouldn't worry about being waylaid by pirates, truth be told. My ship is small and I have nothing of immense value. Sugarcane and its yields, molasses, rum, that sort of thing.
- Edward: There's not a pirate living who'd turn his back on a keg of rum.
- Bonnet: Well, yes... yes, I suppose that's true. You're a natural sailor, Duncan.
- Edward: I did a decent trick at the helm some time ago. Two years before the mast as a privateer.
- Bonnet: Dash my buttons! Your life seems a grand one, if I may say. So full of adventure! How marvelous.
- Edward: I have seen my share of strangeness, aye.
Edward assumed the identity of Duncan Walpole, rescued Stede Bonnet and sailed for Havana.
- If the memory was replayed while Edward wore the shark hunter outfit, it would show him wearing Hidden Blades even when he technically had not retrieved them from Duncan Walpole's body yet.