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"Sail with Old Pew" comes from "Every man jack could ha' sailed with Old Pew"; line 54 of "Derelict - Cap'tn Billy Bones his song", written by Young Ewing Allision, and published in "Treasure Island" from Robert Louis Stevenson.
In "Treasure Island" the evil and murderous David 'Old' Pew seems to be the blind leader of the gang of pirates, which had sailed with him under command of Captain Flint and who are after the treasure map of their former captain. He gives the Black Spot, a death verdict, to his former defected crewmate Billy Bones, which had stolen the map from them.
So concluded by contexts about Old Pew, Captain Flint, and Long John Silver; beeing able to "Sail with Old Pew" means that someone is morally highly corrupted and a fearsome, murderous pirates.
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