The whole crew are taken at gun point, through a trap infested forest, to a large settlement and imprisoned. Silver immediately refuses, but watches helplessly as Flint accepts the deal, offering himself as guarantor.

During a trip to investigate a dead whale, Silver uses his smarts, and reveals how he deceived Flint and stole the Urca gold. Woodes Rogers, Benjamin Hornigold, Dufresne However, Silver turns his silver-tongue on him; rather than betray him to the enemy of his pirate brethren, Silver thinks he knows someone who owes him money … Max. He weasels his way onto Captain Flint’s crew to save his own hide when they attack his merchant ship. All hope seems lost until Julius and his army show up, forcing the Spanish to retreat. Hornigold follows the Walrus back to the Maroons Island, where Flint and Silver pull a daring move to turn the ships broadside on Hornigold.

Not much is known about John Silver's past. Since this is a story that blends reality and story, I like the idea that before joining the Walrus, Silver existed in whatever vague awful void it is that legendary fictional characters live before they’re invented, and then he walked into the story to take his role as “the man from nowhere”. When Max questions why Silver would help her cover up the death of his own crew member, Silver just says that things in Nassau are complicated enough; though it is probably as much in return for how badly their plot with the Urca schedule turned out for Max. With Eleanor still holding the fort, Silver agrees to exchange Max for twenty pirate prisoners. During the battle, a scuffle between Silver and the cook began over an item that had fallen from the cook's grasp. Dragging him unceremoniously back to his shack, Hands intends to turn-in Silver for the bounty. Captain Berringer, however, had his men follow Max to the parley, and his redcoats suddenly arrive at their camp.

Silver continues to support Flint, even as Hornigold turns against him when Flint proposes calling off the attack on the fortress, in exchange for the hostage Abigail Ashe.

As a crewmember aboard Parrish's vessel, Silver witnessed the attack of the pirate ship Walrus. While his morality has always been complicated, over Season Two he gradually becomes loyal to the crew rather than just himself, and they him electing him Quartermaster.

As Rackham’s ship leaves the inlet, Rogers is waiting, and Flint orders him rammed. He chains up Billy in a hut, and tries to convince him that Flint is doing the right thing.

They are interrupted by a large force of well-armed ex-slaves. While there, Silver tries to recruit new men, by warning the pardoned pirates to rejoin Flint or else.

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