Sir Francis Drake was a privateer with papers from the British crown allowing him to plunder on the high seas as long as the crown got a cut of the 'booty.' Being a privateer he would have flown the flag of his home country, in this case Britain. At no time did he work as a regular pirate, though the French of that time would certainly have disagreed, so he would not have flown under any type of Jolly Roger.
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