Stede Bonnet's career as the "Gentleman Pirate" may represent the worst midlife crisis on record. In 1717, Bonnet, a retired British army major with a large sugar plantation in Barbados, abandoned his wife, children, land and fortune; bought a ship; and turned to piracy on the high seas. Though his crew and fellow pirates judged him to be an inept captain, Bonnet's adventures earned him the nickname "the Gentleman Pirate," and today his legend lingers in the annals of pirate history. But why did a man who seemed to have everything give it all up for a life of crime?

For a few years in the early 18th century, from about 1715 to 1720, piracy experienced a golden age. "Stede Bonnet was part of a gang of pirates operating in the Caribbean that are responsible for the images we have of pirates today," says historian Colin Woodard, author of The Republic of Pirates. The popular pirate, as known from Robert Louis Stevenson's Treasure Island to the recent Pirates of the Caribbean movie trilogy, was inspired by these buccaneers. But even during their lifetimes, pirates like Edward "Blackbeard" Thatch (or Teach) and Ann Bonny were romanticized. "They were folk heroes," says Woodard. Though the authorities characterized pirates as "devils and demons, enemies of all mankind," Woodard says, "many colonial citizens supported them. People saw pirates as Robin Hood figures, socking it to the man on their behalf."

Piracy was a lifestyle, a profession and a political cause in the early 18th century. Many of the men who turned to piracy off the American coast were escaped slaves and indentured servants or colonists who had failed to make a living on land. During this period, Woodard says, "ordinary people were upset about the growing gap between rich and poor, and the growing authoritarian power of the British empire." Though a hanging offense (unless one bribed officials), piracy was an attractive option for men in desperate circumstances with some knowledge of seafaring and a deep loathing for authority.

Stede Bonnet had no knowledge of seafaring, having sailed only as a passenger. Moreover, he had no apparent reason to rage against the establishment. Bonnet was born in the 1680s in Barbados and, according to the transcript of his 1718 trial, had "the advantage of liberal education." After retiring from the army with a rank of major, Bonnet bought an estate and settled in as a member of respectable society, where he spent a decade raising a family until he suffered some kind of mental break. A contemporary account of Bonnet's career suggested that "some Discomforts he found in the married state" led to "this Humour of going a-pyrating," but it seems unlikely that a nagging wife alone could be enough to drive a law-abiding gentleman to piracy.

"There have been a number of theories that it was something mental," says David Moore, an archaeologist and historian with the North Carolina Maritime Museum in Beaufort. Moore notes that, according to the legal record, Bonnet borrowed £1700 (about $400,000 today) around 1717. This suggests that he may have been having financial problems, perhaps due to a hurricane, drought or other natural disaster wiping out his sugar crop.

"Bonnet may have been unbalanced," says Woodard. "From the genealogical record we know that there had been disruptions in his life. One of his children had died." Woodard believes that Bonnet's conversion to piracy stemmed from a combination of personal pressures and politics. Though historians cannot be sure, Woodard says that Bonnet was probably a Jacobite, supporting James Stuart as King of England over the German-born George I. Whether out of loyalty to James or simply animosity toward authority, "most pirates at the time thought of themselves as in revolt against King George," says Woodard. "There was a lot of toasting to King James III."

Regardless of his motivation, Bonnet was determined to carry out his plan. Generally, anyone embarking on a career of piracy would begin by seizing a ship. Bonnet purchased his sloop legally. He armed it with ten cannons, hired a crew of 70 and named the ship Revenge. As Bonnet had no obvious enemy against which to revenge himself, it's likely he chose a name that sounded menacing and pirate-esque—indeed, many pirate ships used the name Revenge.

When Bonnet's Revenge was stocked and ready, he ran up a jolly roger and ordered the crew to sail to Virginia, where they would raid commercial vessels. The skill of Bonnet's crew, many of whom were experienced pirates, helped him quickly capture several ships, which were loaded down with the treasures of the trans-Atlantic trade.

After these early successes, Bonnet and his crew sailed south to Honduras, a well-known pirate hangout, to spend their booty. There, Bonnet met the most famous and feared pirate of his day: Blackbeard. Born in Bristol, England, Blackbeard had worked his way up from deckhand to captain of his own ship—the 40-gun Queen Anne's Revenge—and cultivated a reputation for wildness and unpredictability. Bonnet was thrilled to make Blackbeard's acquaintance, and the two pirate captains agreed to cruise together.

After they set sail, Blackbeard realized he was dealing with an amateur and decided to seize Bonnet's command. He kept Bonnet aboard Queen Anne's Revenge and sent his first mate to take over Bonnet's ship, with the consent of Bonnet's crew. The stout, upper-class Bonnet, Blackbeard explained, was not suited to be a pirate captain, and would do better to relax aboard the larger ship than suffer the trouble of commanding his own. Though nominally Blackbeard's guest, Bonnet was essentially his prisoner, and with bruised feelings Bonnet plotted revenge.

When Blackbeard docked his fleet in North Carolina, Bonnet went ashore and returned to find that Blackbeard had stripped and abandoned the Revenge and marooned some 25 crewmembers on a small island. Bonnet took his ship back, picked up the men, and resumed his piratical pursuits, this time with the goal of punishing Blackbeard. Unfortunately, Blackbeard had a head start, so Bonnet had to content himself with seizing merchant vessels. His skills had improved since he had first embarked, and by abusing his crew, killing prisoners and threatening civilians, Bonnet eventually gained a fearsome reputation of his own.

As word spread about the Gentleman Pirate, the governor of South Carolina commissioned Colonel William Rhett to capture him. In August of 1718, Rhett cornered Bonnet at the mouth of the Cape Fear River, and after a violent firefight he managed to arrest the pirates. Though the hotheaded Bonnet declared he would blow up himself and the ship before he would surrender, his men overruled him and gave themselves up as prisoners. In custody, Bonnet tried to take advantage of his upper-class background in appealing to the governor for mercy and blaming everything on Blackbeard. His trial dragged out long after his men had been hanged, and the trial transcript is "one of the most valuable historical records we have about Bonnet and Blackbeard," says David Moore. Finally convicted of piracy, Stede Bonnet was hanged on December 10, 1718, after less than two years of adventure on the high seas.

Bonnet's execution came a month after Blackbeard had met his own bloody end in battle with the British Royal Navy. By the 1720s, the golden age of piracy was over. Captain Bartholomew Roberts, a contemporary of Blackbeard and Bonnet, declared "a merry Life and a short one shall be my Motto," and, as it turned out, that's exactly what happened to most pirates. Though Bonnet's career was beset with misfortune and his life not always merry, he likely had more fun plundering ships than he would have had at home on his quiet plantation. Whatever his motives for becoming the Gentleman Pirate, Stede Bonnet's name would not live on today had he simply been a gentleman.