Lawsuits Are What Bring Us Together: "The Princess Bride" and the Law (Part 1)

September 16, 2026

–Article

Lawsuits Are What Bring Us Together: "The Princess Bride" and the Law (Part 1)

First, a crucial clarification. While The Princess Bride (the wonderful movie) has the frame narrative of a grandfather who reads the book to his grandson, The Princess Bride (the wonderful book) has the frame narrative of a man whose father read it to him, and who wants to share it with his own son. The book is out of print, and the man sends his lawyer to a used bookstore during a blizzard. Although it’s always heartwarming when the lawyer is the hero of a favorite story… Clients: I esteem you; I cherish you; scavenger hunts during snowstorms are outside the scope of my litigation and employment practice. Please call the mergers and acquisitions team.

Can Buttercup recover emotional distress damages from Ryan (a/k/a the Dread Pirate Roberts)?

Promptly after Buttercup and Westley declared their mutual love, Westley was kidnapped by pirates and presumed murdered. Buttercup “never loved again” and “died that day.” In Massachusetts (and this article makes the common-sense assumption that Florin and the Commonwealth have largely identical legal systems), individuals can sometimes recover damages for their own emotional pain because of harm against a loved one.

This type of claim depends on a close, preexisting relationship with the victim. Immediate family counts; Massachusetts is not very clear on which other relationships count. On the one hand, Westley had been working on Buttercup’s family farm for quite some time; they were in love, and he left to earn money for their marriage. On the other hand, for almost its entire length, their relationship consisted of demands for assorted manual tasks and repeated acquiescence.

There might be some room for argument either way—at least at the time that Westley’s ship was captured. But these emotional distress claims are limited to certain relationships because of principles of foreseeability, and abstract questions about errands and “as you wish” became much less important when Westley begged for his life by putting the pirate on actual knowledge that true love was waiting for him at home. Once Ryan knew that Buttercup existed and had a vested interest in Westley’s well-being, Ryan couldn’t have been surprised that Buttercup was perturbed. Yet he spent the next three (3) years keeping Westley as a prisoner and threatening to kill him in the morning.

The bigger issue for Buttercup’s lawsuit is that, to recover emotional distress damages, the loved one typically must have witnessed the harm or its immediate aftermath. By the time Buttercup was reunited with Westley, he wasn’t just not captured, but a thriving, rock-climbing small-business owner.

But Inigo could sue the Six-Fingered Man for murdering his father in front of him, right?

Oh, definitely.

Did Westley tortiously interfere with Vizzini’s business deal with Humperdinck?

Prince Humperdinck hired Vizzini’s gang to frame a rival country for the abduction and murder of Princess Buttercup, thus smoothing the road to war. Westley (now a/k/a the Dread Pirate Roberts) hunted the kidnappers and blocked Vizzini from holding up his end of this deal. In Massachusetts, interference with someone else’s contractual or business relationship is not legally actionable unless the interferer acted with “improper means or motive.” There’s no improper motive here. True love is a passable motive. Not as good as mutton, lettuce, and tomato, but on the sunny side of the law.

Westley’s means are more questionable. At first, Westley merely followed Vizzini and the gang. Then he drew blood from Inigo and knocked both Fezzik and Inigo unconscious. Still, the facts are on Westley’s side. Violence would typically count as “improper means,” but before Westley put his left hand to his sword, Inigo had already provided a useful disclosure that he was planning to kill him. So far, so defensible. But then, as Vezzik was poised to kill Buttercup, Westley counter-offered a battle of wits to the death. Now, Massachusetts jurisprudence does not offer many contractual interference cases centered on iocane powder. But I expect a jury would likely think that the man who out-dueled Inigo and out-wrestled Fezzik, yet left them both alive, could have rescued Buttercup without killing Vizzini. Quite plausibly, Westley wanted to kill the mastermind with a knife to his true love’s throat. Westley’s means are balanced precariously on lightning sand.

That said, a person is liable for interfering with a contract only if he knows or should have known about it. Did Westley know Humperdinck was behind it? I think so. In the book, when Humperdinck introduces Buttercup to Florin, of the people gathered to see her, “three of them were planning to murder her,” and “in the farthest corner of the Great Square——in the highest building in the land——deep in the deepest shadow——the man in black stood waiting.” We don’t know the details (that’s what depositions are for), but Westley did not just happen to see a boat with a captured princess. He knew there were dark plots—dark contracts—against her.

But in the end: No, Westley is not liable for tortious interference. An agreement to murder a princess to incite a war is illegal, illegal contracts are void, and there is no liability for interfering with a void contract. For a similar reason, Prince Humperdinck can’t sue Vizzini (well, Vizzini’s estate) for breach of contract.

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Lawsuits Are What Bring Us Together: "The Princess Bride" and the Law (Part 1)

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