TDQ Investigates: Inconceivable Plot Hole In “The Princess Bride”

The Dread Pirate Roberts

Toy manufacturers, known for their impeccable safety records, noticed the potential problem and took action.


When soon-to-be-Princess Buttercup is told the truth about her fiance Westley’s “death” as the two of them are traipsing through the Fire Swamp in the 1987 Rob Reiner classic, “The Princess Bride,” part of that truth was that Westley was not killed by Dread Pirate Roberts after his ship had been attacked when he left Buttercup five years earlier. He wasn’t killed, but did learn that there’d been two other Dread Pirate Roberts since the original one, who’d been retired fifteen years and was living quite comfortably in Patagonia. And the Dread Pirate Roberts who captured Westley was so enamored with him, that he bequeathed the Dread Pirate Roberts moniker to Westley himself.

When now-alive-and-well Westley asked Buttercup why she didn’t put her entire life on hold for that five years and agreed to marry Prince Humperdinck, Buttercup answered that, well, Westley was dead. Westley responded, “Death can not stop true love. All it can do is delay it for a while.”

Well, can true love help overlook the fact that Westley became an infamous, murdering, thieving pirate?

It completely gets swept under the rug that Westley himself played Dread Pirate Roberts for two of the five years he was missing, admittedly amassing his own fortune carrying on the name of the pirate who never takes prisoners. Nobody has a problem with this? Buttercup is fine that her handsome, obedient farm boy became a blood-thirsty, lying, pillaging pirate? It’s inconceivable.

Now, we’re all for true love. Heck, we’re all for this movie. We love “The Princess Bride,” almost every part of it. We love the sword fights, we love Andre the Giant, we love Miracle Max. We even love the love story, unlike Fred Savage’s character. But we just. Can’t. Get. Past. The fact that he’s a pirate! And nobody else seems to care.

Vizzini, kidnapper of Buttercup, berater of Andre the Giant and would-be war-instigator, he dies. Count Rugen, a major bad guy, dies, allowing Inigo to get his sweet revenge on him 20 years hence. Prince Humperdinck gets to live a long life alone with his cowardice; the guy who deserves to die at the hands of a pirate gets to live.

Those justices are all fine and good, and clearly, the message is that Westley is a “Pirate-With-A-Heart-Of-Gold.” But like Long John Silver (the literary character, not the restaurant), PWAHOGs still can’t be going around killing innocent people on the high seas without suffering the consequences.

And don’t tell us that the torture machine that killed Westley makes it all right. He suffered a few minutes then died. Not buying it. Two years of piracy and murder don’t get absolved by a few minutes of extreme agony before death. And he was brought back to life a few hours later. Come on!

We want answers. We want the truth. How can an oversight such as still not be addressed 25 years after the movie came out? Rob Reiner? S. Morganstern? Fred Savage? Little help?

Maybe we’ll go straight to the PWAHOG himself, Cary Elwes, the very talented actor who played Westley. Maybe he can explain to us how piracy and murder are not a big deal. But not likely.


You are now informed. Go and do likewise.

2 thoughts on “TDQ Investigates: Inconceivable Plot Hole In “The Princess Bride”

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