The pirate theory is where Oak Island begins. Not as history, but as a story people believed in enough to start digging. When Daniel McGinnis found that depression in the ground in 1795, the name on everyone's lips was Captain Kidd. More than two centuries later, the question of whether pirates could have built the Money Pit remains open. It is the oldest theory, the most popular, and in many ways the hardest to kill.
The Legend That Started It All
The original story, first recorded in print in 1863, tells of a dying sailor from the crew of Captain Kidd who confessed that treasure worth two million pounds had been buried on an island "east of Boston." The tale had been circulating among New England settlers for decades before McGinnis ever set foot on Oak Island. When he found that circular depression beneath an old oak tree, with a ship's tackle block hanging from one of the branches, it was the Kidd legend he thought of first. That assumption shaped everything that followed. The Onslow Company, the Truro Company, and every early expedition dug with pirates in mind. The Money Pit was, from its very first excavation, understood as a pirate vault.
Captain Kidd and the Hidden Maps→
Pirate Country
The pirate theory rests on geography as much as legend. Mahone Bay, where Oak Island sits among more than 360 islands, was ideally suited to piracy. The bay takes its name from the French word "mahonne," a type of low-lying barge used by pirates who frequented these waters. Natural mountain barriers shielded the bay by land, while the Tancook Islands at its mouth offered shelter from the open Atlantic. Anyone docking on the south shore of Oak Island would have been invisible from the bay's entrance, hidden behind a dense canopy of oak trees that gave the island its name.
During the Golden Age of Piracy, roughly 1690 to 1730, Nova Scotia was largely unsettled by Europeans but heavily trafficked by ships. The coastline offered hundreds of hidden coves and deep harbours where a vessel could anchor without being seen. The rich fishing grounds off Newfoundland and Nova Scotia drew thousands of fishermen and sailors every summer, and historian Dan Conlin has noted that pirate crews regularly visited these waters to recruit from the fishing fleets and stock up on food and supplies before heading south as cold weather arrived. The region was one of four areas central to the Golden Age, valued less for what could be taken from it than for what it could provide.
Documented pirate activity in and near Nova Scotia confirms the pattern. Peter Easton operated a fleet of up to 40 ships from Harbour Grace, Newfoundland, as early as 1612, raiding European fishing fleets along the coast. In 1720, the pirate Ned Low terrorised fishing fleets at Shelburne. That same year, Bartholomew Roberts raided Canso and captured ships around Cape Breton before attacking the harbour at Trepassey, Newfoundland, where he seized 22 merchant vessels and 150 fishing ships. By the mid-1720s, the governor of Fortress Louisbourg was so alarmed by the ongoing pirate threat that he requested additional naval protection from France. For more than a century, pirates and privateers treated Nova Scotia's coastline as a place to recruit, resupply, careen their ships, and disappear.
The Pirates
Captain William Kidd is the most famous name attached to the Oak Island story and the one whose legend started the digging. His confirmed burial of treasure on Gardiners Island in 1699 proves that at least one pirate did hide valuables along the Atlantic coast. Henry Every, the "King of Pirates," pulled off the richest pirate raid in history when he seized the Mughal ship Ganj-i-Sawai in 1695 and then vanished completely. His treasure was never recovered, and 17th century Yemeni coins consistent with his plunder have since turned up at sites across Rhode Island and Massachusetts, proving his crew passed through New England waters. One version of the theory places Kidd and Every as partners in a communal bank on Oak Island, hiding their combined riches in a shared vault.
The communal bank theory extends further. Beginning around 1625 and spanning into the 1700s, pirates operating out of Port Royal, Jamaica, including Sir Henry Morgan, Jean Levasseur, and Bartholomew Sharp, may have used Oak Island as a collective stash over decades. Edward Teach, better known as Blackbeard, adds another thread through his famous boast that he buried his treasure "where none but Satan and myself can find it." Peter Easton, arguably the wealthiest and most powerful pirate of the early 17th century, operated from Newfoundland with a fleet large enough to rival a navy. Marty Lagina has named Easton as the most likely pirate candidate for Oak Island.
Peter Easton, the Pirate Admiral→
Blackbeard, the Devil's Bargain→
La Buse and the Unsolved Cryptogram→
Sailors, Soldiers, and Specialists
The standard objection to the pirate theory is engineering. The Money Pit, with its precisely layered platforms, its fills of charcoal, putty, and coconut fibre, and its apparent flood tunnel system, required skills that most pirate crews did not possess. Pirates were sailors and fighters, not civil engineers. The objection holds if "pirate" means a disorganised crew between raids, but the line between pirate and privateer was thin and frequently crossed. Privateer crews, operating under government commission, routinely included former naval officers, experienced navigators, military engineers, and tradesmen drawn from merchant and military backgrounds. Peter Easton held a royal commission before turning pirate. William Kidd sailed under letters of marque from the King of England. Blackbeard served as a privateer during Queen Anne's War.
Among ordinary crew, skills varied widely. The Cornish miner's pick recovered from 127 feet during William Chappell's 1931 excavation has drawn attention from pirate theorists who note that Henry Every was known to recruit west countrymen, many of whom would have had experience working the tin mines of Cornwall. A privateer crew with access to military engineers, carpenters, and miners could command a broader range of construction skills than the popular image of piracy suggests.
The Case Against
Scale remains the strongest argument against the pirate theory. A shaft over a hundred feet deep, with layered oak platforms, imported coconut fibre from the tropics, and a flood tunnel system engineered to protect it, represents months of organised labour by a large workforce. The coconut fibre alone, found in large quantities at Smith's Cove, implies supply chains reaching into tropical latitudes, a level of logistics beyond anything documented in pirate operations. And a project of this size would have been difficult to keep secret. Pirates drank, talked, and moved between crews. Beyond the dying sailor legend, no confession, rumour, or boast connecting a specific pirate crew to Oak Island has ever surfaced.
The Simplest Explanation
The pirate theory persists because it answers the most basic question about Oak Island: why there? Small, wooded, uninhabited, sheltered in a bay already known to pirates, accessible by sea but invisible from the mainland. The geography fits, and the timeline works. Carbon dating of wood and other materials recovered from the pit has returned dates ranging from the early 1600s to the mid-1700s, a window that encompasses the careers of Easton, Kidd, Every, Blackbeard, and dozens of other pirates operating in Atlantic waters. The pirate theory is the oldest explanation for Oak Island, and whatever lies beneath the island, the pirates got there first in the imagination.
