Well, as a Canadian , I have to throw my lot in with Peter Easton! Though not well known, he was likely THE most successful pirate. He is a folk hero in Newfoundland, and very famous in the Maritimes, though interestingly, not so much in the rest of Canada.
to whit:
from Wikipedia, because I am too lazy to write a whole biography, though I likelyy will later:
Peter Easton (c. 1570 – 1620 or after) was a pirate in the early 17th century who operated along the Newfoundland coastline between Harbour Grace and Ferryland from 1611 to 1614. Perhaps one of the most successful of all pirates he controlled such seapower that no sovereign or state could afford to ignore him and he was never overtaken or captured by any fleet commissioned to hunt him down.