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Westley as the Dread Pirate Roberts.

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 is then released at a convenient port, a new crew hired, and the former Roberts stays aboard as first mate. The constant reference to "Captain Roberts" establishes the new Roberts' persona. After the crew is convinced, the former Roberts leaves the ship and retires on his earnings.

Equipped with a holocaust cloak and a wheel barrow, Fezzik impersonates the Dread Pirate Roberts to frighten the guards away from the castle during the wedding.

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 to kill him. The "please" arousing his interest, Roberts asks, "Why should I make an exception of you?" 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' confession to Buttercup as they travel to the Fire Swamp:

Well, Roberts had grown so rich, he wanted to retire. He took me to his cabin and he told me his secret. 'I am not the Dread Pirate Roberts', he said. 'My name is Ryan; I inherited the ship from the previous Dread Pirate Roberts, just as you will inherit it from me. The man I inherited it from is not the real Dread Pirate Roberts either. His name was Cummerbund. The real Roberts has been retired fifteen years and living like a king in Patagonia.'

Westley goes on to explain that the method works because Roberts' notorious reputation inspires overwhelming fear in sailors. Ships immediately capitulate and surrender their wealth rather than be captured, a fate they imagine to be certain death. A pirate operating under his own name rather than Roberts' is said to be incapable of such infamy: "No one would surrender to the Dread Pirate Westley."

In both the movie and the novel, Westley indicates that he plans to retire after reuniting with Buttercup. In the movie, he suggests that Inigo Montoya might succeed him. However, in the novel, no mention is made as to who is to succeed Westley as the Dread Pirate Roberts. Ironically, at their first meeting, Inigo Montoya tells Roberts that "There's not a lot of money in revenge," but Roberts' ship is named Revenge, and it is that ship which makes him rich. In the first chapter of Buttercup's Baby (the supposed sequel to the novel), which is included in the 25th anniversary edition of the book, Goldman refers to 'Pierre', who is in charge of the pirate ship Revenge during Westley's absence and next in line to become the Dread Pirate Roberts. By the end of the chapter, Westley and his companions leave the ship again, presumably leaving Pierre once again in charge; but no mention is made of an official transfer of the title of Dread Pirate Roberts.

Holders of the title[]

When Inigo expresses uncertainty about his life now that his revenge is complete, Westley asks him if he has considered piracy, as he would would make an excellent Dread Pirate Roberts.

Holders of the title Dread Pirate Roberts include:

  • The original Roberts, retired fifteen years in Patagonia at the time Ryan picked Westley to be the next Dread Pirate Roberts
  • Clooney, the original Roberts' first mate
  • Cummerbund
  • Ryan
  • Westley, who presumably retires shortly following the end of the novel.
  • Inigo Montoya, who presumably inherits the title from Westley after the end of the movie.
  • Pierre, who is in line to assume the title after Westley in the novel.