John "Calico Jack" Rackham is the quartermaster on the Ranger in the West Indies. He is in a relationship with Anne Bonny. Rackham's father was a tailor in Leeds whose business failed after an embargo was enacted.
During the events of Black Sails: Season 1 Episode 1 I. played by Toby Schmitz
As Gates is leaving Mosiah's hut, he is spotted by Rackham and Rackham goes and tells Singleton. Singleton confronts Mosiah, who is with Levi, and is upset that he is now going to back Captain Flint. As Mosiah and Levi are walking away, they are stopped by Rackham and Anne. Anne kills Levi and Captain Charles Vane steps out from the shadows. Later, Max tells Rackham that she has something that he might want to buy.
During the events of Black Sails: Season 1 Episode 2 II. played by Toby Schmitz
Rackham asks Anne where Vane is and after she shows him, she tells him that the Prizemaster is waiting in the tent. The Prizemaster counts out 5,000 pesos worth of pearls and hands the bag towards Rackham. Vane walks in and asks Rackham what he is up to. Rackham tells him about Flint's search for the location of the L'Urca de Lime. Vane criticizes Rackham's plan, and in turn, Rackham points out that Vane hasn't been getting any leads from Eleanor Guthrie lately. Frasier appraises the pearls for Max. Max agrees to the payment and tells Rackham to go to the Wrecks at sundown in order to receive the schedule.
Vane barges in and accuses Max of lying about the schedule and Rackham notices John Silver looking through the peephole and tells Vane. Rackham and Vane go to the Wrecks in the evening and an Old Man walks up to them and asks for the pearls. Vane yells that Silver will have to appear to them if he wants the pearls. Vane stabs the Old Man to death and Old Man 2 walks up and asks for the pearls. Billy Bones and Flint arrive at the Wastes and they all begin to chase Silver. While Rackham is searching for Silver he comes across a syphilis victim and stumbles backwards into the ocean, spilling the pearls.
During the events of Black Sails: Season 1 Episode 3 III. played by Toby Schmitz
Hamund and some other Ranger crew members threaten Rackham over him promising they would have a big score and also that they now are down 5,000 pesos. Hamund then tells Rackham to quickly make things right. Rackham sits down next to Gates and casts doubts in his mind about him being the captain of Captain Benjamin Hornigold's ship during the attack on the L'Urca. Rackham suggests to Vane that he join in the attack with Flint against the L'Urca and says the crew will get five million pieces of eight and it will make Vane look good in front of Eleanor. Eleanor, Rackham, Vane, Flint and Gates have a meeting and Flint immediately brings up that Vane killed Mosiah. After some haggling each party comes to an agreement on terms. As Vane and Rackham are walking back to their camp, a Ranger Crew Member tells Vane that Max is all his. Vane then tells Rackham to get Max on a boat so she can leave.
As Rackham is sneaking Max to the boat, he is stopped by Hamund who tells him that the crew will decide when Max leaves. Eleanor hears Max screaming and runs out of Vane's tent and sees Hamund raping Max. Eleanor declares that Vane's crew from now on will be cut off from the island and its resources unless they elect a new captain and join Flint. Anne starts to walk towards Flint, but Vane threatens her. Eleanor tries to comfort Max, but Max tells her that Eleanor is the cause of everything by not leaving with her. Max then walks to Vane and says she will stay until her debt is paid.
During the events of Black Sails: Season 1 Episode 4 IV. played by Toby Schmitz
Rackham finds Vane passed out in his tent from opium. Rackham then leaves after complaining about Vane's physical state. Rackham tries to have Gruenwald sell Vane's hauls as if it were his own, but Gruenwald is worried that if Eleanor find out then he would also be blacklisted. As Rackham and Anne are walking, Noonan calls out to Rackham. Noonan demands that Max be returned and threatens to come and get her by force.
During the events of Black Sails: Season 1 Episode 5 V. played by Toby Schmitz
Vane, Rackham and Anne go to the brothel. Rackham hands Mrs. Mapleton a piece of paper where Noonan has apparently handed over ownership of the brothel to Vane. Mrs. Mapleton tells Rackham that she knows something is afoot and agrees to it if she gets a raise. Hamund and some other pirates walk into the brothel and tells Rackham, Anne and Vane that Eleanor is finished. Hamund gets upset when neither Rackham or Vane offer to join him in harassing Eleanor and leaves. Rackham has Mrs. Mapleton tend to Max. Later, Rackham watches as Vane takes a boat and leaves the island.
During the events of Black Sails: Season 1 Episode 6 VI. played by Toby Schmitz
Hamund walks towards Max's tent and Anne stands in his way. Slade tells him that Anne doesn't want anyone touching Max anymore. Rackham tries to defuse the situation and Hamund snickers at Anne as he walks past her into Max's tent. Hamund and the rest of the Ranger crew break into a room where Rackham and Anne are and confront him. Hamund then points at Anne and says she must have stolen the pearls. Rackham denies it and Hamund shows him pearls he found in Rackham's tent. Anne and Rackham lead Hamund, Slade and the rest of the Ranger crew to where she says the pearls are hid and Hamund and the others are ambushed and killed. Anne tells Rackham that Vane isn't coming back.
During the events of Black Sails: Season 1 Episode 7 VII. played by Toby Schmitz
Anne is having sex with Rackham when she complains about his erectile dysfunction. Rackham tells her that he has a lot of things on his mind and that the brothel they own isn't making a profit. Anne then leaves Rackham naked, tied to the bed. Rackham tells Distressed Whore that she isn't making enough money and will have to leave. Distressed Whore starts to cry and Alice gives Rackham five pieces of coin. Max walks up to Alice and tells her that she knows Alice just serviced Captain Hallendale and he gave her more money. Alice argues with Max, who slaps her and then admits to Rackham that she was lying and will never do it again.
During the events of Black Sails: Season 1 Episode 8 VIII. played by Toby Schmitz
Rackham walks down the stairs to a table at the busy brothel. Mrs. Mapleton tells him that the bursar told her that she was no longer going to receive her part of the brothel's profits. He tells her that he is garnishing her wages for all the money she stole from the brothel. Mrs. Mapleton threatens to tell everyone what happened to Noonan. Rackham then fires her and Max brings up that none of the powerful merchants will care what Mrs. Mapleton tells them as they are all enjoying themselves at the brothel. Mrs. Mapleton angrily walks away and Rackham gives a cheers to Max. Anne gets upset with Rackham for firing Mrs. Mapleton. Later, Vane confronts Rackham with Mrs. Mapleton and accuses him of betrayal and says that he will tell everyone that he betrayed men for a woman.
During the events of Black Sails: Season 2 Episode 1 IX. played by Toby Schmitz
Rackham is using the toilet when Impatient Pirate starts banging on the door and complains that he has been waiting ten minutes to use it. Rackham walks out of the restroom and is confronted by Pirate Thug who calls him the Crew Killer and then has his friends beat Rackham up. Rackham goes to the brothel and Anne asks him what happened after seeing his broken nose. Anne asks who did it to him and he tells her that she can't kill all of their enemies. Eleanor has a meeting with Rackham, Max and Anne and complains to Rackham that Captain Hallendale failed to capture a ship, because he is spending too much time at the brothel. Max tells Eleanor that she sold the information to Ned and Eleanor warns her not to meddle in her affairs again. After the meeting, Anne angrily tells Rackham that either Max is turned into a prostitute again or Anne will deal with her.
During the events of Black Sails: Season 2 Episode 2 X. played by Toby Schmitz
As Anne and Max are talking, Rackham sees them. Rackham confronts Max about seducing Anne and Max tells him that there is nothing he can do about it. Anne wakes up in the middle of the night and goes to Max's bedroom and they have sex. Rackham catches them and offers a compromise that Max will provide all leads to him and then he and Anne will gather a crew and act on those leads.
During the events of Black Sails: Season 2 Episode 3 XI. played by Toby Schmitz
Rackham wakes up to an empty bed and asks Distressed Whore if Anne is still in Max's bedroom and then tells her to tell Anne that he has left. Rackham tries to recruit a crew, but fails. He tells Anne that Max is trying to get between them. Rackham and Anne return to the bordello and Vane asks Rackham and Anne to sit with him. Vane tells them that he wants to repair their reputations and he is doing it because of Max. Max whispers something to Vane and Vane shakes Rackham's hand publicly. Rackham celebrates with Anne about getting a crew and she invites him to have sex with her and Max.
During the events of Black Sails: Season 2 Episode 4 XII. played by Toby Schmitz
After Max, Rackham and Anne's threesome, Alice knocks on Max's door and tells her that she is needed. Rackham goes out to the balcony and notices the prostitutes are not working and Idelle tells him that a Spanish warship is anchored in the bay and rumor is that it belongs to Flint. Max tells Rackham that it is his fault for them being in competition over Anne. Max brings him to speak with Idelle, who tells him that Mr. Featherstone, the navigator on the Colonial Dawn is looking to find another captain and offers to get Featherstone to join Rackham. Anne reassures Rackham and tells him that she knows that Max is trying to play them against each other. Max walks over to Rackham and Anne and tells them that Featherstone tomorrow will join Rackham and Anne.
During the events of Black Sails: Season 2 Episode 5 XIII. played by Toby Schmitz
As Anne, Rackham and Max are having a threesome, Anne notices Max paying attention to Rackham. They are then interrupted by cannon ball explosions. Charlotte shows Rackham her design for his banner along with Idelle and Featherstone. Rackham rejects her design and Charlotte gets upset. Rackham tells Featherstone that he wants to set sail as soon as the bombardment stops. Featherstone starts to tell Rackham that the other pirates want some changes made to the ship agreements, but stops when Anne walks up. Anne wonders if Vane will survive the bombardment. Rackham asks Max if any of Flint's crew have gone to the brothel and Anne thinks that Flint's crew were told not to go to the brothel so they couldn't divulge a secret. They approach Charlotte and ask her if Logan has visited her and asks her to find out about the Urca gold. Idelle asks Rackham to come with her and brings him to her room and Featherstone tells Rackham that the crew has two problems with the articles, one is Max getting a cut of the spoils and Anne. Rackham walks up to Anne and tells her what Featherstone told him and that he plans on going without her for now, until he gains the crews' trust. After he tells her, Anne gets up and walks away.
During the events of Black Sails: Season 2 Episode 6 XIV. played by Toby Schmitz
Rackham smiles as he sails on his new ship and Featherstone tells him that they should be about to come upon the True North. Featherstone offers to help Rackham if he needs it during the True North's capture and tells him that he heard his post on the Ranger was a political one. The Lookout spots ship sails and Rackham gives the order to take the True North. The Lookout then yells that a ship is following from behind them. The True North Captain is tied to the mast and Linus Harcourt and his crew board the True North. Rackham introduces himself and Linus tells him that he has three options, their crews fight it out, Rackham and Linus fight, or they come to an agreement on splitting the spoils.
Linus tells Rackham that he knows that it must be Rackham's first day as a captain and Rackham becomes sensitive when Linus mentions his banner. Linus gives Rackham his idea of how things should be split, which is unequal. Rackham shows Featherstone the list of what Linus is willing to share and Featherstone thinks they should accept it. Rackham attacks Linus and manages to slice him in the neck. They fight and Linus starts to beat Rackham, but then dies from his wound. Rackham tells Linus' crew that Linus refused to make an equitable deal and has Mr. Haines release the crew from the True North. He then invites the Goliath's Quartermaster to come and make a more equitable deal.
During the events of Black Sails: Season 2 Episode 8 XVI. played by Toby Schmitz
Featherstone storms into the brothel and goes to Max's office and asks her and Rackham how he is supposed to gather that much gold and bring it back without anyone else knowing. He asks where they are going to put the gold once they get it. Max then tells Featherstone to continue what he is doing and the plan will work. Max notices Rackham is upset and he admits that he never really knew Anne. Featherstone, Rackham and Max come up with a plan to store the gold and Rackham comes up with the idea to store the gold in the fort. At the fort, Featherstone admits to Rackham that he is in love with Idelle. Rackham has the doors to the fort broken down and he and his men enter the fort and find it empty, except for a crucified Richard Guthrie.
During the events of Black Sails: Season 2 Episode 9 XVII. played by Toby Schmitz
Max tells Rackham to leave as soon as possible for the Urca gold. Anne returns to the island and speaks with Rackham. Rackham tells her that he thought he would never see her again and she warns him and Featherstone as they are about to be attacked by Pirate Thug and the other thug. Anne kills Pirate Thug and then kills the other thug. Rackham, Featherstone and Anne go to the brothel and Max tells them that Mr. Stayton and Mr. Atz are dead and tells them to leave as soon as possible.
During the events of Black Sails: Season 2 Episode 10 XVIII. played by Toby Schmitz
Featherstone finally tells the crew of their mission to get the Urca gold. Rackham asks Anne why she came back and she tells him that she realized that they are two-halves of one person. Street Kid Runner tells Max that Rackham is back and she and Idelle run to the beach where Rackham shows them all the gold they recovered.
During the events of Black Sails: Season 3 Episode 1 XIX. played by Toby Schmitz
Rackham is reading the Jamaica Courant from Wednesday, August 5, 1715, while Celeste plays the cello when Anne complains to him about work not being done on the fort. Anne asks him what his plan is and Vane walks in and yells Rackham's name. Vane accuses Rackham of knowingly sending him after a slave ship so they could use the slaves to rebuild the fort. Rackham complains that no one on Nassau wants to work and he has to use slaves. Vane watches as the slaves are forced to repair the fort and Rackham tells him that when he first saw all the gold, he thought he was going to make something great.
During the events of Black Sails: Season 3 Episode 2 XX. played by Toby Schmitz
Warren goes to Featherstone to get 500 pieces of gold. Rackham realizes that Warren was asking for 500 pieces two days ago and Warren tells him that he lost the last amount. Featherstone suggests to Warren that he withdraw a smaller amount due to his inability to keep track of his gold, but Warren asks for 500 pieces.
Max tells Rackham her idea of exchanging some of the gold for pearls. Rackham starts to complain that he rarely sees Anne and thinks that Anne will always choose to be with Max, but Max assures him that Anne will always choose Rackham in the end. Idelle drops a sack of gold coins in front of Rackham and tells him that she found it at the inn by the bar. She tells him that Warren left the last sack of gold in the privy. Vane and Blackbeard go to speak with Rackham and Blackbeard insults Rackham. Rackham explains their goal of defending Nassau, but Blackbeard asks him why they are determined to defend it.
Pirate Recruit 1 and Pirate Recruit 2 recognize Blackbeard and ask to join his crew. Blackbeard says that when he was young, if someone wanted to join a crew of repute they had to fight someone else to get on the crew. He then complains that now people think they can just ask please to join a crew. Pirate Recruit 1 and Pirate Recruit 2 walk away and Blackbeard says that by giving Nassau prosperity, Vane and Rackham have changed Nassau for the worse. Pirate Recruit 1 then walks back to Blackbeard after beating Pirate Recruit 2 in a fist fight. Rackham tells Max and Anne that he agrees with exchanging some of the gold for things of equal value and asks Max not to tell Vane or Flint.
During the events of Black Sails: Season 3 Episode 3 XXI. played by Toby Schmitz
Max tells Rackham, Vane and Featherstone about the incoming fleet and when they are expected to arrive. Rackham comes up with an idea to protect the bay with various crews including those belonging to Burgess, Woodall and the Cockrams. He continues that if they present a large show of force, the British may turn around and leave.
Captain Throckmorton and some other captains argue with Rackham about his plan to do a show of force when the English fleet arrives. Jacob Garrett says they need to have a plan if the bluff works and Vane gets upset with all the complaining. Rackham assure the captains that Flint will return and reminds them that they were given gold coins in assurance that they would defend Nassau. Blackbeard walks into the room and says that Flint was killed while being chased by Hornigold. Rackham figures out that Vane plans on leaving with Blackbeard and tells Anne.
Hornigold and Dufresne take a boat to Nassau. Hornigold gives a speech written by Woodes Rogers offering pardons to the pirates. He then continues that their is a bounty placed on Vane for 10,000 pounds. Throckmorton then walks up to Hornigold to receive his pardon as do other pirates.
During the events of Black Sails: Season 3 Episode 4 XXII. played by Toby Schmitz
A group of pirates including Knocking Pirate gather at the fort and demand that Rackham give them Vane. Rackham has the gate opened to the fort and then shoots Knocking Pirate dead before closing it again. Anne wonders why out of everyone, Vane was the only one that wasn't offered a pardon. Featherstone tells Rackham that their crew have voted and they and they want Vane removed from the fort as they think the new governor might let them keep the fort and the gold.
Warren sees Rackham and asks where he has been. Rackham tells Vane, Anne and Featherstone that he has set the explosives and they are about to go off. He tells Vane that he will cover Vane's escape, but he and the others plan on staying. Rackham's explosives go off and later, Rackham laments to Anne that they were so close to cementing their names in history.
During the events of Black Sails: Season 3 Episode 5 XXIII. played by Toby Schmitz
Rackham and Anne are escorting their share of the gold when Rackham tells Anne that he cannot make himself change his name and is going to return to Nassau to get his pardon.
During the events of Black Sails: Season 3 Episode 6 XXIV. played by Toby Schmitz
As Rackham is walking, he sees a wagon full of wood and asks Ex-Pirate 1 where it is going. Ex-Pirate 1 tells him it is going to the fort to fix it. Featherstone sees Rackham and wonders why he is back at Nassau. Rackham tells him that he is annoyed to see how easily Rogers has made everything work. The Pardon Clerk calls for the next in line and when Rackham tells him his name, he is surrounded by soldiers and told Rogers would like to speak with him.
Rackham is brought to Rogers' office and tells Rogers that he read his book. Rogers tells Rackham that he needs him to return all of the gold he took or they are all dead. Rogers tells Rackham that Spain knows about the gold being exchanged for other items. Rackham relates to Rogers of how he remembers as a boy the way men spoke of Henry Avery and wanted people to speak of his name in the same manner. Max is brought to Rackham and she tells him that everyone will know that it was Rackham that saved Nassau and Rackahm tells her that he sent word to Anne to take the cache and run. Rackham tells Max that either Rogers will realize he cannot win and leave Nassau or Spain will raze it to the ground and Nassau will be reborn again as a pirate haven and everyone will know that the new pirate haven was brought about by Rackham.
During the events of Black Sails: Season 3 Episode 7 XXV. played by Toby Schmitz
Rogers tells Rackham that he believes Anne will give up the remainder of the cache and says that the last thing he will allow is for himself to be cast as a villain. As Rogers is leaving Rackham's cell, Rackham warns him that Anne will be even more upset when she finds out that she was lied to, and Rackham was never tortured and that everyone is a villain in Nassau.
During the events of Black Sails: Season 3 Episode 8 XXVI. played by Toby Schmitz
Rackham is in his cell and feeds food scraps to a mouse and recommends it leave to see the rest of the world outside the prison. The cell door opens, and Rackham is brought in chains to a carriage where Rogers is sitting along with a chest with Anne's share of the cache. Rogers tells Rackham that he is being sent as a prisoner to the Spanish. Major Rollins tells Rogers that they are ready, and Rackham is surprised to hear that Anne is still alive.
Rogers assures Rackham that his execution will probably be quick. Rackham tells Rogers that as long as Anne is alive, there is a chance she will attempt to free Rackham. Rackham tells Rogers about his father and how his father became an alcoholic after his business failed. He tells Rogers that while Rogers had an easy life, he had to struggle, and yet still caught up to Rogers. Riders are seen approaching and Rackham tells an officer to engage the riders. Rackham tries to choke Rogers, but Rogers punches him unconscious. The riders kill Rogers' escort and shoot the wagon tire, causing the wagon to crash. Two of the riders reveal themselves to be Vane and Anne and Anne kisses Rackham. Flint and Billy grab the chest while Vane and Anne stay behind to try and free Rackham. Vane then has Anne ride away with Rackham. Rackham tells Flint that Vane was captured. Flint tells Billy to bring the cache to the ship while he goes back to save Vane. Rackham and Billy tell Flint that he must return with the cache and Billy says he will agitate the locals to try and prevent Vane from being hanged.
During the events of Black Sails: Season 3 Episode 9 XXVII. played by Toby Schmitz
Flint tells Rackham and Anne that they are not far from the Maroon island. He continues that Hornigold is not that far behind them, but Silver has come up with a plan that might help them make it to shore. Rackham tells Flint that everyone's sacrifices are dependent on the contents of the chest with the cache. Dooley tells Flint that it is time and Flint leaves the room. When they reach the island, the crew of The Walrus and the Maroons unload the supplies. During Mr. Scott's funeral, Rackham tells Flint that he would like to captain The Walrus while Flint leads the defense of the island.
During the events of Black Sails: Season 3 Episode 10 XXVIII. played by Toby Schmitz
Flint digs a hole to bury Rackham and Anne's treasure chest in. Silver asks Flint if he thinks it is a good idea to bury the chest without telling friends and Rackham agrees with Flint that it is best that The Maroon Queen doesn't know. Flint tells Silver that The Maroon Queen knows and she agreed to it as long as Silver knew where it was hidden. The battle begins and Rackham and Anne watch the battle from their ship and Rackham tells Anne of his plan to get a group of their men onboard one of the British ships to disrupt their line. Sails are spotted and De Groot tells them that six ships are heading their way and De Groot thinks they are British reinforcements. Rackham tells Lookout to describe the ships and Rackham realizes that it is the pirate armada.
Rackham and Anne go onto Blackbeard's ship and tell him of the British attack. Blackbeard tells them that Vane is dead and Rogers had him hung. Rackham then asks Blackbeard to join the fight with them. Blackbeard tells Rackham that he doesn't understand why Vane ever had faith in Rackham's ability. Blackbeard tells Ellers, who is disguised as a British Navy sailor along with Blackbeard's other men, to get his logbook. Rackham suggests to Blackbeard that they try to appear to be horribly incompetent, so Captain Chamberlain underestimates them. Blackbeard then follows his advice and raises his pirate flag.
Chamberlain orders his ships to fire upon Blackbeard's ships and Anne and a small group of pirates jump into the water under cover of smoke. Hornigold's Boatswain has his men continue to fire upon Blackbeard's ship, but is then boarded by Anne and the pirates who kill him and his crew. Anne has the pirates on Hornigold's ship fire upon the British Navy ships. Chamberlain then retreats.