Captain Frankie

How about Running the Gauntlet (notably used in the Royal Navy as a punishment for minor theft)... The condemned was prevented from rushing by the master-at-arms with a cutlass and pushed forward by a corporal, while being beaten with rope yarns that were plaited into so-called "knittles" (a word for a string; possibly sound-associated with nettles), which looked like smaller, improvised versions of the cat o' nine tails . The condemned could also receive a dozen lashes from the cat o' nine tails beforehand, so that blows received while running the gauntlet would aggravate the lacerations on his back. An example (alas, not from the right period):

And here be the Pirates of the Saskatchewan (with an EverQuest clip): (Sorry about the triple-post, but it's a maximum of one clip per post)

Here be a song 'bout good ol' Captain Hook (obviously, before he got the hook): http://www.youtube.com/watch?v=hPoymsmSXlU

Here be a fun sailor's song (with a World of Warcraft clip):

Only 6 more months....

And then there is non-food:

No; you shouldn't use the rebel flag; it was just provided for a wolf's head example... Using the second head, here is a quick design (minus the wings), of what it might look like (I found a one-file version of PSP):

Since I don't have a properly-working graphics-program anymore (other than Windows Paint), I'm afraid I can't be of all that much use at the moment... What kind of wolf's head are you looking for? Here are some examples: As for the crossed blades; something like this?

How about an 'Ambachts Roestbikkertje' (Ambacht being my home port, and the rest could be translated as 'Little Rust-Chipper' ), a local herbal liqueur...

Here's a freightening thought: Captain Jack is trying to find the Fountain of Youth (since he wants to be immortal)... What if he finds it, jumps in, and actually becomes younger? Then, the role of Jack Sparrow might be taken over by.... YEP!!!