Questions Remain: How Many Did Wesley Kill as Dread Pirate Roberts?

Sure, the masked man is the good guy and the prince is the bad guy

By now, we’re all familiar with the story of Wesley, the daring farm boy who returned from certain death to save his true love from being murdered by the treacherous Prince Humperdinck. It’s a very nice story: the rustic, innocent lovers reuniting and triumphing over the wicked monarch — what’s not to like? It’s all so neat and tidy. At least, that is, if you take the tale at face value.

What do we really know about Wesley, though? Where exactly has he been all these years? Credible reports had him dead at the hands of pirates soon after he set to sea in the first place. When he reappeared, Wesley had a convenient alibi to explain his reputed death: the famous Dread Pirate Roberts had made an exception of him, in stark contrast to his unyieldingly strict reputation. 

That detail alone should be enough to raise suspicion. Are we certain that this supposed revenant was actually Wesley? Would it not make more sense that Buttercup’s first thought was correct, and the masked man was actually Roberts himself? After all, he only “revealed” his identity after Buttercup managed to assault him and escape his custody.

In this matter, we have no choice but to accept the Princess’s revised testimony that the mysterious figure actually was her long lost love. She is the only living person who knew this simple farm boy before his disappearance. Of course, if we believe Wesley’s story, that only incriminates him further. He says that he somehow managed to be promoted to captaincy and assumed the role of the Dread Pirate himself. 

Now, some of you may wonder why he did not reject the offer so that he could return to his dear Buttercup before her engagement to the duplicitous Humperdinck, which is a fair question. Wesley impugned the Princess’s faithfulness for accepting another’s proposal when, by all accounts, he was dead. Why would he think it was okay for him to go pleasure cruising around the world while his love languished at home? At best, he’s a massive hypocrite.

I, however, have a darker query. In none of his testimony does Wesley dispute the fact that the Dread Pirate Roberts kills all of his captives — with himself being the notable sole exception. He has never once claimed that he changed this policy during his time holding the title of Dread Pirate. He even uses this reputation to his advantage while storming the castle gates to rescue Buttercup, implying that he has, indeed, carried on this violent tradition.

How many innocent lives has Wesley taken? How much blood has he spilled while the woman he claims to love mourned for him? He certainly didn’t become a master swordsman, formidable wrestler, or deft poisoner by showing mercy. Did he really rescue his true love from a miserable life, or did he come ashore for amorous plunder, leaving a trail of bloodshed in his wake? We may never know.