|Status||Deceased (killed by Hornigold)|
|Portrayed by||Richard Lothian|
During his months crewing with Captain Flint, Dobbs becomes a member of the vanguard. During a raid, however, amidst the war against civilisation, he loses his footing, which Flint interprets as him losing his nerve. Once they return to the Walrus and Flint demands he gets replaced. Billy Bones tells Flint that he just lost his footing and doesn't think it had anything to do with his nerve, but Flint orders he be replaced. John Silver reluctantly convinces Dobbs to quit his position as the vanguard, telling him that his skill in the rig is too valuable. He later informs Flint of this.
Flint sails the crew through a storm in order to escape Benjamin Hornigold, who has become a pirate hunter for the Royal Navy, refusing to surrender in exchange for pardons. Dobbs is part of the deck crew and mans one of the ropes. However, they are unable to raise their t'gallants and the wind nearly capsizes the ship, and the men on deck are thrown around by the waves. Flint is eventually forced to cut away the t'gallants of the main and foremast, righting the ship. Billy then advocates that they weigh anchor and ride out the storm below, but Flint says that Hornigold will be looking for them when it dies out. Billy orders Dobbs and Palmer to man the starboard braces while Flint ties himself to the helm and tries to steer them through the storm. The crew survives, but they are becalmed in the Sargasso Sea with little food or water.
The crew spends over three weeks in the Doldrums surviving on minimal rations and what little they can catch with the eel nets. During this time, two crewmen accuse each other of stealing rations. Silver tries to deliberate, but gets nowhere and Flint executes the two. As supplies dwindle even further, Silver and Flint row out to a whale carcass to try and salvage its meat but it is too far rotten for consumption. However, they catch several sharks to feed the crew. Shortly thereafter, the wind returns, and they sail to an uncharted island.
The crew is captured upon arrival at the Maroon Island. The Maroons lead them to their camp upriver, where they are imprisoned. Several of the crew are chosen to be tortured and interrogated before being killed. The crew spends several days imprisoned in cages preparing to be worked to death. However, Flint is able to negotiate a partnership with the Maroon Queen and her husband Mr. Scott where they will join forces to retake Nassau and then launch a rebellion of pirates and slaves to end colonial rule in the New World.
The crew takes on a number of Maroons and sails to Ocracoke Island to try and reclaim the Pirate Fleet. While they sail to Ocracoke , the crew works on repairing the fore and main masts, which were damaged in the storm. As they try and haul a spar up to the tops of the masts, the lashing becomes undone and the spar comes crashing down to the deck. Dobbs becomes angry after barely dodging the falling wood, and rushes towards the Maroon, calling him an idiot and saying that if he can’t tie a rope he shouldn’t be on a ship. Flint, Billy Bones and Kofi then step in to prevent things from escalating.
Flint asks what happened and Dobbs explains that the Maroon’s lashing came undone, which he had showed him how to do it ten minutes ago. Dobbs also adds that someone could have been killed. Flint replies that Dobbs showed the Maroon incorrectly. Dobbs is irritated by this, and says he knows how to tie a lashing. Flint repeats that if the Maroon tied it wrong, then Dobbs instructed him incorrectly. Flint then pulls him close and emphasizes how they persuaded the Maroons that they need the pirates, but the pirates certainly need the Maroons. With that, everyone continues their work.
Later, Dobbs takes revenge on one of the ex-slaves, by mutilating him. Quartermaster John Silver eventually brought the Maroon Queen’s daughter, Madi, into the fold. Madi swallowed her pride to maintain the alliance, and released her man with orders to say nothing. On Silver’s part, he had his men pin Dobbs in his bunk with a blanket and beaten.
However, to redeem himself, Silver gave Dobbs a key role in the battle when overwhelming English force attack the island. After clearing the beach, Dobbs seemed to betray the pirates. He leads the English into an ambush, where Flint’s concealed men began slaughtering them. In the ensuing chaos, Benjamin Hornigold killed Dobbs.
“I sailed with that crew for months. Then they take the side of those fucking savages over a man who was supposed to have been their brother. Truth is, they didn't give a shit about me except that I did their bidding, so now I'm ready to see it end, and I can help you end it” Dobbs to Hornigold.