Rackham
Background
John "Calico Jack" Rackham is the quartermaster on the Ranger in the West Indies. He is in a relationship with Anne Bonny.
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.