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Singleton is a pirate on The Walrus in the West Indies.

During the events of Black Sails: Season 1 Episode 1 I. played by Anthony Bishop

A merchant ship is being attacked by the Walrus. The Walrus catches up to the merchant ship and most of the remaining sailors on the merchant ship are killed. Captain Parrish shoots at Singleton, but instead kills his own man and as Singleton is about to kill Parrish, Captain Flint stops him. Singleton makes a speech to the captured sailors telling them that their true enemy is Parrish. Singleton is about to torture Parrish when Gates pulls him away and Flint asks Parrish where the schedule is. The pirates land at Nassau on New Providence Island and 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 Flint. As Mosiah and Levi are walking away, they are stopped by Rackham and Anne Bonny. Anne kills Levi and Captain Charles Vane steps out from the shadows. Back on The Walrus, Flint speaks to the crew that includes Morley and apologizes for their small hauls and tells them the truth of what they have been chasing. He says that a crew member discovered their plans and betrayed them and accuses Singleton of being that person. Gates tells Singleton that he has a choice, a trial or combat and Singleton chooses combat. Flint and Singleton fight and Flint ends up beating Singleton to death.