While pirate life is often depicted as free spirited and easy going, the reality aboard a pirate ship was terrifying for many in the early 18th century: pirate captives. Pirate crews were constantly looking for new recruits. They regularly took young men off captured ships and forced them, often at gunpoint, to sail with their crew. When taken aboard, these captives faced a terrible dilemma. They could refuse to join the pirates and suffer countless whippings and beatings for their defiance, forced into months of shipboard labor like cooking, carpentry, manning sails, and standing cold, nighttime watches. Or captives could sign on as members of the pirate crew and improve their situations aboard ship – but risk being tried and hanged if the crew was ever captured by authorities. It was almost impossible to walk the fine line between these two violent extremes.

A year in the life of a young sailor named William Phillips, who was captured in the summer of 1723, underscores the perilous situation these men encountered. Phillips was one of four members of a pirate crew that tried unsuccessfully to escape from the pirate ship in February 1724. Phillips himself had no part in the planned escape, but he was led by a brutal man named Samuel Ferne, who had been an original member of the pirate crew but was now desperate to get away. Having taken over a captured ship, the men spent three days trying to sail away from the pirate crew, only to be recaptured and brought alongside. Ferne fired his pistol across the water at his “completely despotic” captain, but missed. The pirates returned fire with a blast of one of their heavy guns, sending the four deserters below deck running for cover.

Hiding below deck, Ferne told the young William Phillips to go back up to talk to the enraged pirate captain. It was a fateful decision for Phillips, who had been taken captive by the pirates four months earlier while sailing aboard a vessel bound for the Portuguese island of Madeira. Phillips had initially refused to sign the ship’s articles and join the pirate crew, but he eventually did because, as he claimed at his trial several months later, the pirates threatened to “blow his brains out” at gunpoint. When Phillips reemerged from below decks during the standoff, the pirates looking over at him could only assume he was now aligned with the mutinous Ferne. One of the pirates immediately fired with a pistol. The shot struck Phillips’ left leg, and within a matter of days his wounded limb had to be sawed off. He was luckier than Ferne, who was killed only moments later when the enraged pirate captain attacked him with a sword.

The frightening turn of events in February 1724 reveal the terrible dilemma in which pirate captives found themselves. Phillips was one of hundreds of young men who were forced aboard pirate ships during this era. While whippings at the mast and threats at the point of a gun were often used to compel captives to join a crew, other young men taken captive during this era were lured by the more comfortable lifestyle and “airy notions of riches” that the pirates described. John Brown, a 29-year old sailor from England, was captured by Edward Low’s pirate crew near the Cape Verde Islands in October of 1722. The pirates “beat him black and blue to make him sign the articles,” he later claimed. But it’s hard to know the truth, because Brown soon told another sailor he “had rather be in a tight vessel than a leaky one, and that he was not forced.” Some young men claimed their decisions to join the pirates were clouded by alcohol. William White, who joined a pirate crew led by the captain John Phillips in 1723, testified at his trial that “he is sorry he should commit such a sin, that he was in drink when he went away with” the pirates.

Authorities were highly skeptical of claims by young sailors that they were forced aboard a pirate ship. “The plea of constraint, or force (in the mouth of every pirate) can be of no avail to them,” said John Valentine, the advocate general who prosecuted the case against members of Low’s crew in 1723. “For if that would justify or excuse, no pirate would ever be convicted.” And courts convicted both Brown and White at their trials – they were soon hanged in celebrated public executions. This proved to be nearly fatal for William Phillips. At a trial held in Boston in May 1724, Phillips told the court he was forced to sign the pirates’ articles at gunpoint. But Phillips knew that he would be presumed guilty. After his left leg was cut off, the pirates tried to send him back to shore with a fishing schooner captured by the pirates near southern Nova Scotia. But Phillips refused to go, “saying if he should they would hang him.”

Indeed, even though several of Phillips’ crewmates testified that he was a forced man, he was narrowly convicted by a plurality of the judges, even as six other captives were unanimously acquitted. Phillips then heard the fateful judgment of the court: “You, William Phillips, are to go from hence to the place whence you come and from thence to the place of execution, and there you are to be hanged by the neck until you are dead, and God of His Infinite Mercy save your Soul.”

Yet at the last moment, Williams and one of the other convicted pirates were granted a reprieve, and Governor William Dummer wrote to London asking for a royal pardon of the two pirates. The pardon was granted a year later.