Rackham
Background
John "Calico Jack" Rackham is the captain of a pirate ship 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.