The Mystery of Oak Island

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On Oak Island, everybody gets up early. By dawn, with the fog turning into a drizzle, the crew is hard at work. I’ve taken refuge inside the rusted hulk of an old tank car, where I can take notes without the ink smearing. Up the hill, men cluster around a drilling rig that is pounding its way into the island’s interior. Shouts and curses echo through the fog. “Sand!” someone yells. “We’re in sand, damn it!”

All around me lies the evidence of the hunt: big Ingersoll-Rand air compressors, enormous pump heads, piles of steel casing, acetylene tanks, strange infernal machines, and bright aluminum ducts snaking their way across the ground. The chill September rain is slowly coating them all.

In 1909, a young law clerk named Franklin Delano Roosevelt trod this very ground with pick, shovel, and high hopes. Admiral Richard Byrd, Errol Flynn, and Vincent Astor all at one time or another took an interest.

Here in Mahone Bay, about forty miles southwest of Halifax, Nova Scotia, I am at the site of the most intensive treasure hunt in history, a hunt that has lasted 193 years, cost millions of dollars, and killed six men. The raison d’être for it all is a narrow, water-filled shaft called the Money Pit—and what may be hidden in its muddy depths. To date, not one penny of treasure has been recovered. Nor does anyone know what might be buried here, who buried it, or why. The island stubbornly refuses to yield anything but the most tantalizing and infuriatingly ambiguous clues.

But the Oak Island mystery may soon be solved. Triton Alliance Ltd., a group of Canadian and American investors, is making the biggest assault yet on the Money Pit. They are digging a shaft of gargantuan proportions twenty stories into the very heart of the island. In doing so, Triton will either find treasure and uncover an important archaeological site, or they will have burned up $10 million digging an empty hole.

The mystery of Oak Island began in the summer of 1795, when a teenage farm boy named Daniel McGinnis decided to do a little exploring. He rowed out to Oak Island, tied up his boat, and started poking around. His story, along with those of the many who have followed, goes something like this:

At the seaward end of the island, the thick forest of red oaks suddenly gave way to an old clearing, dotted with a few rotted stumps. In the center stood an ancient oak with a sawed-off limb. The limb showed evidence of rope burns and, in some versions of the tale, had an old ship’s tackle hanging from it. Directly underneath, the ground had subsided into a shallow depression. From this, a young boy could draw only one conclusion: buried pirate treasure.

McGinnis returned the next day with two friends, Anthony Vaughan and John Smith, and they began digging. At two feet they struck a tier of flagstones. On pulling these up, they found themselves digging in what appeared to be an old shaft excavated in the hard glacial till, a mixture of clay, sand, gravel, and rocks. The shaft had been filled with loose dirt and they could see old pick marks in the walls.

At about ten feet they hit a platform of rotten logs, the ends embedded in the clay. They eagerly ripped these up and kept going. At twenty feet they struck another platform, and yet another at thirty. With no end in sight, and no doubt their chores seriously in arrears, the three boys gave up—but only for the time being. Both McGinnis and Smith later bought land on the island, hoping eventually to reach the vast treasure that they were sure must lie at the bottom of the pit.

When a well-to-do man named Simeon Lynds heard the story, he enlisted workers, including the three young men, in a new assault. Work began in 1803. At forty feet they struck another log platform. They continued to hit platforms at regular intervals, and they also encountered a layer of charcoal, a layer of putty, and a layer of fibrous material that was later identified as coconut fiber.

At ninety feet they found something really exciting—a flat stone inscribed with mysterious figures. They quickly tore up the platform beneath it. Soon, water began seeping into the pit and they found themselves bailing as much as digging. As night came on, they probed the muck at the bottom of the pit with a crowbar and struck something hard at the ninety-eight-foot level.

“Some supposed it was wood,” one researcher wrote later, “and others called it a chest. This circumstance put them all in good spirits and during the evening a good deal of discussion arose as to who should have the largest share of the treasure.”

There would be no sharing of treasure. The next day the diggers arose to find the pit sixty feet deep in water—salt water. Bailing proved to be as futile as bailing out the ocean.

This first, failed effort was only the beginning. Syndicate after syndicate was floated to get to the bottom of the pit. They dug, pumped, excavated, drilled, dynamited, trenched, cribbed, bulldozed, and blasted the island, turning the eastern end into a cratered wasteland. At some point in the early nineteenth century the original hole was nicknamed the “Money Pit,” although the only direction money seemed to go was into the pit, not out of it.

In 1849 diggers built a platform over the Money Pit and cored down with a pod auger, a primitive type of drill. The drilling engineer, Jotham B. McCully, later stated that the drill struck wood at ninety-eight feet, dropped through twelve inches of space, then rattled through “twenty-two inches of metal in pieces,” struck more wood, another twenty-two inches of metal, then wood, then soil. The auger failed to bring up any metal except three links of a gold chain which, McCully theorized, “had apparently been forced from an epaulette.”

Around this time, treasure hunters made another curious discovery. One day a workman was sitting alongside the cobbled beach at Smith’s Cove, a small cove five hundred feet east of the Money Pit. He noticed that as the tide ebbed, the beach “gulched forth water like a sponge being squeezed.” The crew immediately built a cofferdam around the spot and excavated the beach. To their astonishment, they discovered that the beach was a fake—that is, it had been made to look like a beach but was in fact a giant filtering and drainage system. Underneath the cobbles they found thick layers of eel grass and coconut fiber lying on top of an elaborate system of box drains. The drains led, like the five fingers of a hand, to a point opposite the Money Pit. They were, apparently, the head of a “flood trap” designed to keep the pit filled with water.

The reader may well wonder how the original diggers intended to retrieve their treasures from such a death trap. Current theories, for which there is yet no evidence, are convincingly simple. Once the pirates—let us call them that for the moment—had dug the Money Pit sufficiently deep, they would have started side shafts that sloped gently back toward the surface. Treasures would have been hidden in the ends of these side tunnels, three hundred to five hundred feet away from the Money Pit but perhaps only thirty feet below the surface. The pirates would have known the direction and distance from the Money Pit, left highly visible as a decoy, to each of the treasure troves and it would have been a simple matter to dig them up.

In 1897, drillers brought up more strange clues. From the 155-foot level, the drill bit carried up a half-inch-square piece of parchment with two letters written on it with a quill pen. In another hole the drill was stopped cold at 126 feet by what seemed to be an iron plate. A magnet was raked through grit brought up from the hole and it pulled out thousands of iron filings. A year later, dye dumped into the pit emerged from the seabed at Smith’s Cove, providing more evidence of a tunnel connection. But it also emerged from the South Shore Cove, establishing the existence of two flood tunnels, thus making things more complicated.

Everyone assumed that whoever would go to that much trouble must have buried an enormous treasure. Around the turn of the century, fortune hunters estimated it at $10 million; by the 1930s, this had doubled; by the sixties, some people were talking about $100 million or more. Today it is pegged at $500 million to “several billion.”

So what has been the problem? Why in the world hasn’t someone been able to get to the bottom of the Money Pit?

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Excerpted from The Lost Tomb by Douglas Preston. Copyright © 2023 by Splendide Mendax, Inc. Reprinted with permission of Grand Central Publishing. All rights reserved.

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