Dooley is a pirate on The Walrus in the West Indies.
During the events of Black Sails: Season 2 Episode 1 IX. played by Laudo Liebenberg
Captain Flint starts to tell The Walrus crew his plan. Logan angrily yells that they should be cutting Flint's lying tongue from his head and Dufresne tells the crew to listen to Flint. Flint suggests they steal the warship and then take the gold. He continues to tell his plan of sending two people to kill any sentries on the ship while the rest of the crew readies an assault. De Groot gets upset with listening to Flint's plan and Flint volunteers to be one of the men to kill the sentries and John Silver volunteers to be the other. Later, Ranking Spanish Sailor looks towards the water and Joji shoots him in the head. Joshua breaks the door down where Flint and Silver are hiding and he and the rest of The Walrus crew kill the remaining Spanish crew. They then manage to steal the Spanish ship and escape.
During the events of Black Sails: Season 2 Episode 2 X. played by Laudo Liebenberg
On his fourth goings on, John Silver tells the crew that Dooley defecated and used his hand to wipe himself. Dooley gets up, punches Silver and then wipes his hand on his face. He then tells the crew about Palmer having sex with the milk goat. Palmer punches Silver, but is then punched by Joshua. A ship is spotted and Logan tells Dufresne that it is flying English colors. Dufresne then decides to attack it. Dufresne manages to take the English ship without a fight. Dufresne and part of The Walrus crew board the English ship and the Merchant Captain whistles and a fight breaks out. Joji kills the Merchant Captain, but the pirates and Dufresne are forced to retreat back to The Walrus. De Groot tells Dufresne that they must retreat and Dufresne freezes once again. Flint tells Dufresne that they have to sink the English ship or no one will ever surrender to Flint's flag again and then Flint starts giving out orders. The English ship is then sunk.
During the events of Black Sails: Season 2 Episode 3 XI. played by Laudo Liebenberg
During Silver's going on, he tells the crew that Joji has been masturbating onto the figurehead. He then tells the crew that they will be anchoring a mile from Nassau so they won't be seen. Dooley says he wants to vote on the matter. Silver reminds him that they are sailing a Spanish warship and would more than likely be fired upon by Captain Benjamin Hornigold's fort. Dooley still insists he get a vote and Logan diffuses the situation. Later, Flint tells the crew that he will tell Captain Charles Vane that he and his men must leave by sunrise tomorrow or they will attack the fort.
During the events of Black Sails: Season 2 Episode 4 XII. played by Laudo Liebenberg
Flint walks to his and Hornigold's crew and tells them to fire on the fort.
During the events of Black Sails: Season 2 Episode 5 XIII. played by Laudo Liebenberg
Flint tells his crew to cease fire and De Groot repeats the order. Flint then orders his crew to prepare to move ashore.
During the events of Black Sails: Season 2 Episode 8 XVI. played by Laudo Liebenberg
Silver tells the crew a story of when he was on a merchant vessel and when he first saw Charles Town. He continues about how he and the rest of the crew saw the execution of Solomon Little. Silver ends his story by telling the pirates that the entire population of Charles Town is eager to see them dead.
During the events of Black Sails: Season 2 Episode 9 XVII. played by Laudo Liebenberg
Mr. Scott sees Dooley staring into the water and Dooley tells him that he saw something in the water. Billy Bones sees Vane's men climb onto the deck and warns his fellow pirates. A battle erupts and during it, Vane kills Joshua and then fights Billy. The battle ends and Jenks tells Vane that the Man-'o' War is secure. The Boat Captain tells Vane and his men that Peter Ashe has a message for them, Flint has violated Peter's trust and he will be placed under arrest. Flint will be put on trial and hung and if the pirate ship remains, it will be sunk. Vane gets free of Vincent and brings Vincent and Silver on deck. Vane tells his crew that Nassau is strongest when it is feared and suggests they free Flint.
During the events of Black Sails: Season 2 Episode 10 XVIII. played by Laudo Liebenberg
Yardley has Baymen Lieutenant grab Silver and Flint's crew stand up to block them from leaving with Silver. Billy headbutts Yardley and a fight breaks out, but Silver is dragged away. As Jenks is about to slit Silver's throat, Flint's crew storm into the room and Billy kills Jenks while Yardley and Baymen Lieutenant are also killed. De Groot tells the crew to raise the sails and Mr. Scott tells them to get ready to sail. Billy has the crew fire upon the blockade ships. Flint and Vane get into a boat and start to row towards the Man-o'War and are fired upon by William Rhett and some militia men. The Man-o'-War opens fire on Rhett and kills him. Flint has Vane's men released and has the ship continue to fire upon Charles Town.
During the events of Black Sails: Season 3 Episode 1 XIX. played by Laudo Liebenberg
Hallendale's ship is spotted floating in the water. De Groot tells Silver and Billy that maybe the ship was abandoned. Dooley thinks they should check the ship out in case the crew needs help and Silver agrees, but Flint thinks it is a bad idea. Flint goes onto Hallendale's ship with Billy, Joji, Dooley and a few other crew members. They find it empty except for the body of Hallendale chained to his desk. They look through his logbook and find the last few pages with We All Die Alone written over and over. Billy says that Hallendale was marooned and Flint notes the only water left for Hallendale was sea water. Flint realizes it is a trap and they return to The Walrus. A ship appears and Flint notes that the ship is under British colors and is a pirate hunter. The ship pulls up next to The Walrus and Hornigold tells the crew that he will give them pardons if they surrender. Flint tells his crew that he could never surrender to England after they have taken so much from him. He says that England must be afraid of them if they are offering them all pardons. Flint then tells the crew that they are going to sail into the nearby storm. As Hornigold's ship is about to fire on The Walrus, Flint has the crew sail towards the storm and Hornigold follows him.
During the events of Black Sails: Season 3 Episode 2 XX. played by Laudo Liebenberg
Flint sees Hornigold turn back and orders the topgallants to be taken down. Billy asks Rogelio if the halyard is free and Murtaugh tells him that it is stuck. Murtaugh climbs to the top of the mast to cut the halyard and the ship is hit by a knockdown wave. Some of the men are knocked overboard and De Groot tells Flint that they must take the topgallant in. Flint cuts a rope and part of the mast breaks away and goes flying away with Murtaugh. Flint tells Billy to have everyone go down below while Flint stays on deck to steer the ship. Dooley goes to the bottom of the ship and finds Silver staring the body of Muldoon.
During the events of Black Sails: Season 3 Episode 3 XXI. played by Laudo Liebenberg
On day 18 on The Walrus, Dooley pulls up a basket full of eels from the ocean. Palmer and Oates are accused of stealing rations. Silver holds a trial to figure out which one of them stole the rations. Oates insists he would never steal from the crew. Palmer says that during everything that has happened, he has never complained. Flint walks up and shoots Palmer in the head and then starts to reload his gun. Flint then shoots Oates in the head.
On day 21, Billy tells Flint that they spotted a whale carcass. De Groot says that whale's float after they rot, but Silver insists they go after it and tells Flint he is coming also. Silver and Flint bring a shark back to the ship and feed the crew with it. After the wind returns, the crew of The Walrus arrive at an island and go ashore.
During the events of Black Sails: Season 3 Episode 4 XXII. played by Laudo Liebenberg
The pirates from The Walrus are gathering water and food on the island while also making camp. A group of Maroons capture the rest of The Walrus crew. As they are being brought to the Maroon camp, Dooley wonders if the Maroons will be less harsh on them due to them fleeing a few slaves, but Billy reminds him that they sold more than they freed. Silver's leg goes out from under him and Twitchy Pirate tries to escape. Flint and his crew are brought to a village where they meet The Maroon Queen who demands to know who their captain is. She asks Flint what his name is and then asks who their quartermaster is. Silver steps forward and The Maroon Queen asks him how they found the island and who else knew where they were. She asks him if he was in her position if he would take the word of a pirate and then has one of the crew taken away while the rest of them are placed inside a cage. Dooley asks Flint what is going to happen to them and Ben Gunn tells him that those who survive the initial purge will then be forced to do hard labor.
During the events of Black Sails: Season 3 Episode 5 XXIII. played by Laudo Liebenberg
A group of maroons carry Mr. Scott ashore on a stretcher and Billy, who can't see who it is, asks Silver who is on the stretcher. Ben tells them that Mr. Scott is the king of the maroons. Later, Flint tells his crew about Mr. Scott's idea, but first he must convince The Maroon Queen to agree to the plan. He tells them that if he feels The Maroon Queen will not agree to the idea, then he will take The Maroon Queen hostage and force her to release his crew. Flint is brought before The Maroon Queen and Dr. Howell shows Billy the knife Flint was supposed to use to take The Maroon Queen hostage left on the ground. Afterwards, Billy and the rest of the crew are freed by Kofi.
During the events of Black Sails: Season 3 Episode 6 XXIV. played by Laudo Liebenberg
Dobbs starts yelling at a Maroon when a piece of the mast almost falls on a crew member. Flint asks what is the matter and Dobbs tells him that the Maroon's lashing came undone even though he just showed him how to do it. An island is spotted and De Groot hands Flint a spyglass and he looks out at Ocracoke Island. Flint and his crew land on the beach and are greeted by Blackbeard. Later, Blackbeard challenges Flint to fight with pistols and then swords over who shall claim the fleet.
Dooley and Ellers prepare Flint and Blackbeard's pistols. The Referee Pirate gives the rules of the engagement which includes no quarter given. In the first round, Flint manages to shoot Blackbeard in the temple, but Blackbeard manages to get up and attacks Flint with his sword. Blackbeard beats Flint in sword-fighting and as he is about to kill Flint, Vane steps in and forces Blackbeard back. Blackbeard then walks up to Flint and tells him take Vane with him and leave.
During the events of Black Sails: Season 3 Episode 7 XXV. played by Laudo Liebenberg
De Groot tells Flint that Nassau has been spotted. Silver goes to a tavern with Billy, Dooley and Joji and walks over to the desk holding the pardon books. He warns the former pirates inside that they have betrayed Flint. Tavern Bystander says that Flint is dead. Silver tells the people in the tavern that everyone whose name is in the pardon book originally pledged to defend Nassau and then takes the book. He says that anyone who meets them on the beach will be accepted back, while those who don't rejoin will face consequences. Dufresne stands up and calls Silver half a man and calls Flint's threat weak. He walks up to Silver and calls him an invalid and Silver hits Dufresne in the face with a tankard and then crushes his head with his stump. Once they are back on the ship word spreads among the crew about what Silver did to Dufresne. The next morning, De Groot calls to Flint. Flint looks to the beach and sees Woodes Rogers in a tent on the beach. Flint takes a boat to the beach and sits down in front of Rogers. Vane and Anne Bonny board The Walrus and explain their plan to Flint of getting Rackham back.
During the events of Black Sails: Season 3 Episode 8 XXVI. played by Laudo Liebenberg
Dooley tells Silver that he needs to speak with him and takes Silver to the cargo hold where Dobbs, Joji, and Wayne are standing over Chidi, who has been beaten up and has his hands tied. Dobbs says that in the Maroon camp they killed Parker, Louis, Graves, and Simon and Chidi was the one who chose them to be killed. Dooley suggests they either kill Chidi or let him kill Dobbs, but Silver decides to tell Madi what has happened. Madi is brought to see Chidi and Silver tells her that Dobbs is the one responsible and he will be punished. Madi cuts Chidi loose and tells Silver that Chidi will tell the others that he offended Madi and was punished by Kofi. Later, while Dobbs is sleeping, he is beaten by Dooley and a few other pirates.
During the events of Black Sails: Season 3 Episode 9 XXVII. played by Laudo Liebenberg
The Royal Lion continues to chase The Walrus. Dooley tells Flint that it is time while he is talking with Rackham and Anne and Flint leaves the room. Leadsman calls out the surface depths to Dooley who then repeats it to De Groot. The Leadsman continues to yell out depths and De Groot tells Flint that both anchors are ready. Flint tells Mr. Williamson to hard to port and to drop the anchors and The Walrus turns to face the Royal Lion. The crew of The Walrus and the Maroons then unload the supplies.
During the events of Black Sails: Season 3 Episode 10 XXVIII. played by Laudo Liebenberg
The British troops land on the island and the pirates and Maroons begin firing at them. Flint orders his men to concentrate their fire on the artillery mortars. The mortars start to fire on the island defenses and Dooley suggests they retreat, but Flint eventually tells his men to retreat. Later, Hornigold's men and the British troops start firing upon the Maroon camp. The pirates and Maroons ambush Hornigold and Major Rollins' men and start to slaughter them. Flint yells at the retreating British to tell Rogers that he is coming.