Q: Does the Captain’s Hat protect me from being Plundered, like the Cutlass or Pistol?

A: The short answer is yes, you can’t Plunder the Captain’s Hat itself, but you can Plunder anything else from the Captain (unless he has the Cutlass or the Pistol).

Think of it this way: while the Captain outranks the owners of both the Cutlass and Pistol when Plundering from them, it is not, in fact a weapon which protects the Captain’s own Keepers.