People: Fly in the Ointment

Today's Golden Age pirate is famous, not for plunder, seamanship, or success, but because of his actions prior to his execution. He is mentioned briefly in Captain Johnson’s History of Pyrates, dwelled on at length in Marcus Rediker’s Villains of All Nations and written about by Cotton Mather. As is so often the case, we know next to nothing about William Fly’s background, but his death made a splash that resonates into our own time.


Fly, according to Johnson, was born to “very obscure parents” probably around the turn of the 17th to the 18th century. By 1726 he was bosun aboard Captain John Green’s brig Elizabeth headed out from New England for the coast of West Africa. Many who have written about Fly assume that Elizabeth was one of those ships involved in the so called “triangle trade” carrying rum to Africa where it would be traded for slaves. There is nothing specific in the record to confirm this, but it is certainly a possibility. What we do know for sure is that Elizabeth was involved in some sort of merchant endeavor and that Green did not run a happy ship.

Before the ship left for blue water to cross the Atlantic, Fly and his captain were butting heads. At his trial, and even before, Fly complained bitterly of the “bad usage” suffered under Captain Green by him and his mates. Fly’s comments are in line with the classic argument as to why merchant seamen turned pirate. Small crews, low wages, grueling schedules, unreasonable discipline, poor food and a host of other trials sent men over the edge to desertion, mutiny and even murder.

Fed up from virtually the start of Elizabeth’s cruise, William Fly organized a mutiny. One night in the spring of 1726, he and fellow crewman Alexander Mitchell pulled Captain Green out of his cot, dragged him up on deck and subjected him to a beating. When he was half-unconscious, they and others tossed Green over the ship’s side. Still prepared to fight for his life, Green caught part of the rigging and held on tight. One of the mutineers grabbed an ax, several of which would have been kept handy to cut away rigging in foul weather, and chopped off his captain’s hand. The first mate, Thomas Jenkins, followed the captain over the side. The final target of the men’s ire, an unnamed surgeon, was spared as “they might find him useful”. He was shackled in bilboes instead.

Fly was quickly chosen as the new captain of Elizabeth. He immediately changed her name to Fame’s Revenge and he and his men set out a-pirating. They took five prizes in all and each one appears to have been a poorly laden merchant. Fly made it his signature move to torture or in other ways punish the captains he took hostage. He notoriously whipped Captain John Fulker of the John & Hannah so viciously that the man nearly died.

It seems that William Fly was no more popular as captain than Green had been. A group of his men, possibly those pressed into service from prize vessels, rose up and took Fly’s ship. They turned it over to the authorities of Boston in June of 1726. Fly and a dozen of his crew were incarcerated and set to be tried for piracy and murder on the high seas.

At this point, the notorious Puritan minister Cotton Mather enters the picture. Sent by the judge in the case to exact confessions and guide penitence in the pirates, Mather ran into a man that he himself called “a most uncommon and amazing instance of impenitence and stupidity and what spectacles of obduration the wicked will be” in William Fly. Mather writes that, when confronted with the crimes of mutiny and murder, Fly would, no pun intended, fly into an uncontrollable rage. At one point the pirate ranted that he “… would not own myself guilty of any murder, our captain and his mate used us barbarously…” While Fly does not list specific actions, he laments that “… poor men can’t have justice done us…” no matter how badly they are treated by their nominal betters.

Fly continued his obduration straight up until his conviction and execution. While others convicted with him stood on the gallows and “preached” to the crowd – as Mather had hoped – the ills of drink and rebellion, Fly did exactly the opposite. He came to face death with a “smiling aspect” and eyed the crowd “unconcerned”.

Fly even went so far as to chastise the hangman for “not understanding his trade” and stepped forward to retie the noose with which he would be killed. He then addressed the crowd as he had Reverend Mather, saying frankly that he had “wronged no man”. He went on to say that he wanted those who commanded vessels to “… take warning by the fate of [our] captain… and to pay sailors their wages when due, and to treat them better”. It was an ominous warning from a man who had taken the ultimate step in eliminating his tormenter and was facing death because of it.

Some writers and historians, notably Rediker, have used Fly as an example of the underlying reason for piracy as a life pursuit. In this scenario, William Fly and his fellows stand as anti-heroes bucking the “barbarous” establishment. As this post at Executed Today puts it “… the radical doomed sphere of resistance pirates offered to the enormous cruelty of the developing Atlantic economy…” To my mind, this is overstating the case. From Barbary to the buccaneers, through the Golden Age and into the last days of the privateers, most of the men who went out seeking prizes on the high seas were no more freedom fighters than modern day drug dealers. They were in it for the simple reward of cash. While some men may have had good intentions, it is important to note that Fly’s short career as a sea captain turned out to be no more glorious than that of the commander he killed.

Fly’s body and those of his compatriots were gibbeted on the little island in Boston Harbor known as Nix’s Mate as a “warning to other seamen”. To this day, stories of strange lights around the island – particularly on summer nights – lead some to believe that his ghost still haunts the rocky outcropping. While that, too, is probably overstating the case it is a possibility worth imagining.

Header: Engraving from The Pirate's Own Book