Jolly Roger
Pirate Steve
American Heritage dictionary says "origin unknown" Maybe someone knows?
AdSumADS
Webster's isn't much clearer: Jolly Roger, but there probably isn't much to it etymologically, anyway. The "jolly" is the ironic, gallows-humor accompanying the English pirate tradition, and the English also have a pattern of using such proper names in their slang (the verb, "to roger," [meaning to bone, to use America slang] in particular).
AdSumADS
I found a refrence to one of the slang uses of "Roger" at that time for "beggar."
Lewis Joplin II
JOLLY ROGER - "French buccaneers may have flown a flag called the 'joli rouge' (pretty red) and this term may have been corrupted to 'Jolly Roger' by English pirates when they transferred it to their black flag. 'Jolly Roger' could, however, derive from the 17th-century English word 'roger,' meaning 'rogue or devil.' Or it may come from the widely use Tamil title Ali Raja, meaning 'king of the sea' - English pirates at first pronouncing 'Ali Raja' as 'Ally Roger,' then 'Olly Roger' and finally, 'Jolly Roger.'" From "Encyclopedia of Word and Phrase Origins" by Robert Hendrickson (Facts on File, New York, 1997)
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