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“Teach’s flag depicted a skeleton spearing a heart,
while toasting the devil.
It was designed to intimidate enemies.”

Ri-i-ight. And Jack Sparrow actually existed, too.

Note the date on the illustration in your post. It is dated 1736. Teach died almost 20 years earlier (1718). And that image, along with all of the various pirate “flags” were created in London by engravers trying to please publishers with books to sell.

They could come up with any flag they could think of, and who was going to say boo about the accuracy? And frankly, they did. I have seen what you claimed to be Teach’s flag as Bartholomew Robert’s flag and Charles Vane’s flag depending on the book — and often varying from edition to edition of the book. (I am talking about 18th century books, or modern facsimile reproductions of those books.)

A few years back I decide to do some research on pirate flags to determine what designs were authentic. The fancy pirate flags you see in 19th-, 20th-, and 21st-century books on piracy were all taken from 18th century books written 10 to 50 years after the end of the Golden Age of Piracy (which ended in 1721 or 22, although some pirates lingered on until 1730).

I could not find description in contemporaneous newspaper accounts (1700-1722), although that does not signify since not many are available. So I actually dug up Admiralty court records from that era (back in the early 1800s someone collected court proceedings from piracy trials into some books, and I obtained copies). After plowing through these source, I found no reference to skeletons, skulls-and-crossed bones, or any of the other devices frequently put forward as pirate flags. When flags were referred to the pirates were claimed to have been flying “a black banner” or “a red banner,” which I inferred to be a flag of solid black or solid red. After all, today when someone flies a white flag, it is a solid white flag. This makes a sense to me as having a skull-and-crossbones flag (or similarly-marked flag that could be associated with a pirate flag) aboard your ship would be evidence that your ship was a pirate ship and that you were a pirate. Back in the early 1700s it could not easily be explained away as a joke if you were caught with one in a law-abiding port (and even pirates went to law-abiding ports). On the other hand, every ship had bolts of red, black, white, blue, yellow, etc cloth aboard, and your solid black or red banner could be fairly easily explained away. For that matter, pirates today don’t bother with flags, and I suspect most pirates throughout history did not.

I am not saying it could not have happened, but until I see a contemporaneous official report from a naval captain of an encounter or capture of a pirate than describes one of the so-called pirate flags (other than as a “black banner”) or a Admiralty Court proceedings of a piracy trial from the period 1700-1725 describing such flags, I will believe that all of these fancy pirate flags were the product of Fleet Street circa 1730-60, with subsequent appearances on the high seas being borrowings from these books.