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Pirate Flag Images and Symbols:
Cemeteries and Graveyards were often the inspiration for the morbid imagery such as skulls and skeletons used on pirate flags. Emmanuel Wynne is said to started this trend with his skull and cross bones over an hourglass; this message was that time to surrender was running out. Fearlessness in the face of death was shown with a cup raised in a toast.
A heart pierced with a sword or knife symbolized a merciless death. A spear or dart showed a violent death. A heart leaking drops of blood showed a drawn out and torturous death. An empty fist or cutlass in hand spoke of a swift death. Maybe you can see the theme of death here.
Blackbeard's Flag Meaning
Blackbeard apparently tried to incorporate most all of these symbols. His flag showed a skeleton with horns holding an spear in one hand and hourglass in the other that is pointing to a heart dripping three blood drops.
( An entry in his journal reveals that some felt the Blackbeard flag should show the skeleton with scary tattoos, a black leather jacket, and a Harley to ride, but he felt that was overkill. )