When modern people hear the word pilot they naturally assume one is talking about an individual who handles an aircraft of one kind or another. Just 100 years ago, and certainly before that, the word would have brought something different to mind. Different and yet oddly similar.
A pilot, from the early sea peoples through Viking days and on into the ages of the buccaneers, pirates and privateers, had the specific job of keeping the ship safe and on course near land. Out in open water navigation was done with the aid of the heavens and the compass but near land, particularly in times when accurate charts were a relative rarity, you needed someone who knew the coastal waters like the back of their hand.
In established waterways, a local pilot could be hired. This was a person, usually designated by whatever navy had control of the coast, river road, delta etc., who was an expert on the shoals, bars, sandbanks, coral reefs and so on that might cause harm to a ship. He would not only know the best routes of navigation in the area, but also which specific ways were clear for deeper draft ships such as frigates or men-of-war. As an example the station known as the Balize, at the conjunction of the Mississippi River and the Gulf of Mexico, has had a Master Pilot since the French established the territory, and probably before. His job being to see ships safely in and out of the river. A pilot's fair way was a body of water designated as impassable without the help of a pilot. The fee paid a pilot was known as a pilotage.
The hiring of a pilot was not, however, reserved only to "legal" waterways. Pilots worked the harbors of Tortuga in buccaneering days and Port Royal, Nassau, Charleston and the Outer Banks of the Carolinas during the Golden Age of piracy. The Laffite brothers employed local sailors at their bases in Barataria where the pass between the islands of Grand Terre and Grande Isle can be treacherous, and Galveston where the bar is so high and the pass so narrow that only one ship could enter or leave the harbor at a time.
Independent freebooters who had no steady base might pay a resident fisherman or even kidnap a native of the area to pilot their ship for them. Doubtless this thankless and nerve racking situation would leave the pilot in question shaken if he succeeded and dead if he did not.
Pilots had to be clear headed and knowledgeable and, particularly in the case of the smuggling operations that supported the pirate and privateering industries, prepared to encounter the aggression of the authorities. At least the task was not thankless. A good pilot, like a good surgeon, was highly regarded by seafaring men.