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Question:

what is the term pirates use or would have used to raise a flag?

like if in the olden days pirates wanted to sail the jolly roger.. what would have been some terms or quotes they would have used to sail it?

Answer:

'Hoist' or 'run up' the Jolly Roger. Indeed 'sail' is absolutely the wrong word. You 'sail' a ship.
Hoist the Jolly Roger
Hoist the colors!

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