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At the beginning of The Princess Bride, the only thing known concerning the Dread Pirate Roberts is that he never leaves captives alive.
It is revealed during the course of the story that Roberts is not one man, but a series of individuals who periodically pass the name and reputation to a chosen successor. Everyone except the successor and the former Roberts is then released at a convenient port, and a new crew is hired. The former Roberts stays aboard as first mate, referring to his successor as "Captain Roberts", and thereby establishing the new Roberts' persona. After the crew is convinced, the former Roberts leaves the ship and retires on his earnings.
Westley, the hero of The Princess Bride, is on a voyage to seek his fortune when his ship is captured by the Dread Pirate. While the other passengers are weeping and offering bribery for their lives, Westley simply asks Roberts to please not kill him. The "please" arousing his interest, Roberts asks, "Why should I make an exception of Westley then explains his mission to get enough money to reunite himself with Buttercup. Westley's description of Buttercup's beauty intrigues Roberts to the point that he hires Westley as a personal attendant. While Roberts is continually impressed with Westley's work, he continues to keep Westley's future in doubt by saying each night "Good night, Westley. Good work. Sleep well. I'll most likely kill you in the morning." After about three years, Roberts and Westley have grown close, and Roberts promotes Westley to his second-in-command. Shortly after that, Roberts reveals to Westley that the guise of the "Dread Pirate Roberts" is merely a nom de guerre that he has inherited. In the film adaptation, Westley relates Roberts's confession to Buttercup as they travel to the Fire Swamp:
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