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While crewing a pirate ship alone in a battle with another vessel, Flintlocke ends up in the water, and while lamenting his misfortune is visited by Nadakhan. Two ill-conceived wishes land him first in a burning desert, and then in the freezing Arctic menaced by a Treehorn Queen. When at last Flintlocke wishes to be aboard a pirate ship again, his wish is granted by his induction into the crew of Misfortune's Keep.
Doubloon, a thief with a fast-running mouth, runs into the crew of Misfortune's Keep after escaping from prison. He manages to open a lock aboard ship but is caught, and questions whether there would be an opening for him on the crew. Nadkhan, surprisingly, agrees, but punishes Doubloon's insolence by cursing him. Left with two faces and no voice, Doubloon finds himself bound to the service of Nadakhan.
Dogshank, an ambitious young athlete, fails to excel despite her willingness to cheat, and thus accepts an offer from Nadakhan. Transformed into a hulking brute, she becomes stronger than ever before, and willingly joins the crew of Misfortune's Keep.
Monk, a skilled ship's mechanic, is one day plagued by the appearance of an inquisitive monkey just as Nadakhan comes looking for his services. Monk wishes to become the fastest mechanic alive, with skill that makes it seem as though he and his tools are one, and for the elimination of the irritating primate. Nadakhan grants his wishes by merging Monk and the monkey into a mechanical primate, who soon grants Nadkhan's wish by building Misfortune's Keep.
Sqiffy and Bucko, overly excitable sailors, are fired from their job aboard a steamboat after angering the captain once too often. Their attempts to find other work end with similar failure, as they manage to annoy both Master Chen and Cyrus Borg. Upon spotting a couple of pirates aboard Misfortune's Keep, they begin mocking them, only to be cornered by an irritated Nadakhan. However, the Djinn decides that the pair can be of use, and puts them to work aboard ship.
As a young Serpentine, Clancee had ambitions of being a pirate, despite suffering numerous mishaps as a result of his own inability. However, he was able to join the crew of Misfortune's Keep after accidentally taking the place of another pirate.
Despite the fact that the various Sky Pirates were recruited in Ninjago's "ancient" past, several of the videos feature modern settings and/or characters:
Dogshank is seen competing in modern sporting events in modern clothing alongside other present day people.
Monk, before becoming Monkey Wretch, uses modern tools and also wears modern clothing. He is also seen working on the Destiny's Bounty.
Clancee is shown wearing modern-day human clothing, being cared for by Selma, and in modern buildings such as Darkley's Boarding School for Bad Boys. He is shown as a student of Darkley's, but is also shown being kicked out.
Sqiffy and Bucko's video is in direct contradiction to their introduction in the animated series.