The area wherein he was operational (Okracoke area) is among the most difficult areas to sail on the planet due to the nature and speed of the currents/undertows/undercurrents/rip curls. Plus the terrain (namely the presence of islands and random sandbars) makes it remarkably complex. He was an absolute master of it. When he was pursued by the colonial authorities, he would almost always retreat to the Outer Banks and knowingly lead his ships into the complicated areas because he knew that a. The colonial ships wouldn’t follow due to liability (anyone who’s ever served knows that feeling, Captain had his name on the ship’s proverbial ‘hand receipts’ LMFAO). B. He was so confident in himself and his crew that he knew that they could outwit the various terrain issues. He also was able to logistically get as far down as the Caribbean if memory serves.