The Oak Island Mystery: 200 Years of Buried Secrets (Part 2)

As the mid-9th century unfolded, Oak Island’s mystery had already taken firm root in local folklore and whispered legend. The island had transitioned from a curious oddity to a magnet for treasure hunters across Nova Scotia and beyond. The curious pit at its center, known now in almost reverent tones as the Money Pit, had thwarted every attempt at excavation. And with each failed dig, each washed-out tunnel and lost investment, the air around the island began to change. The optimism of discovery gave way to something darker—an invisible weight pressing down upon the soil and the men who dared to disturb it.

It was around 1850 that the first murmurs of a curse began to echo through the coastal towns. These were not yet bold declarations of doom, but rather uncertain phrases: bad luck, a wicked place, a pit that swallows men whole. The names of those early treasure seekers, once spoken with admiration, now carried a tinge of pity or caution.

The most prominent group of this decade, known as the Truro Company, brought fresh energy and better tools. They arrived with steam-powered pumps and modern boring rigs—equipment far superior to what the earlier Onslow Company had decades earlier. Their plan was systematic and grounded in confidence. This was no ragtag bunch of treasure dreamers; these were engineers, landowners, and businessmen who believed the key to the mystery lay in precision and persistence.

They began by re-excavating the original Money Pit but found it dangerously unstable. Water infiltrated the shaft at the same familiar depth—a cold, unstoppable surge that seemed to rise from the earth itself. Their pumps were more powerful, but even those machines proved no match for the cleverly designed flood system buried beneath the island’s surface. The deeper they dug, the more the water came. And yet, the Truro men pushed onward.

They deployed a new technique: drilling core samples downward through the flooded pit. Their hollow drill, mounted on a platform and manned around the clock, extracted soil and fragments from depths over 100 feet. The samples were odd. One contained traces of cement; another pulled up what appeared to be oak wood and layers of soft clay. But it was the sample at approximately 154 feet that truly electrified the dig team. The drill brought up pieces of what they believed was parchment, fragile, darkened with age, and inscribed with microscopic writing. Alongside it were shards of what seemed to be gold chain links embedded in a strange cement-like substance.

Though small, these fragments were the first tangible evidence of something man-made—something hidden, perhaps even valuable, waiting far below. Theories exploded once more. Had the drill pierced a hidden vault? Was there a stone chamber filled with treasure, sealed in concrete and buried deep beyond reach?

Hope reignited, if only for a while. But the sea, ever faithful to its defense of Oak Island, responded in kind. The pit collapsed. Not only did the central shaft fail, but surrounding tunnels gave way as well. Water rushed in from multiple directions, erasing weeks of progress in mere hours. The heavy machinery groaned under the strain, and exhausted workers were forced to retreat. Some fell ill from gas exposure; others were injured during the collapse. None would find what they had come for.

It was during this time that stories of spectral visions and bad omens began to circulate among laborers. Workers swore they saw strange lights over the trees at night—flickering glows with no source. Tools vanished, only to reappear in different locations. A wooden beam fell from the pulley system without warning, injuring a crewman who swore he heard a whisper just before it hit. One foreman, according to letters from the time, refused to return to the island, calling it “a place cursed by old devils.”

Superstition grew as failure mounted. And then came death.

One cold October morning, a man named Maynard Kaiser was working on a recovery platform when a rope snapped. He fell into the pit, helpless, and drowned before he could be reached. His death was sudden and brutal, and it would not be the last.

With each tragedy, the tale of the island’s curse spread further. It was said in hushed tones that seven must die before the treasure would reveal itself. No one knew where this figure came from. No written record confirmed it. Yet the number echoed eerily through every account, passed from dig site to pub, from journals to newsprint. And still, they came.

By the end of the 1860s, two more companies had formed and dissolved. The failure rate was staggering. No one had surpassed the original 90 to 100-foot depth without flooding or collapse. The engineering complexity of the island’s traps continued to astound even the most learned geologists of the era. Some tried to tunnel horizontally from other parts of the island. Others attempted to block the flood tunnels at Smith’s Cove, filling trenches with clay and rock. A few even suggested detonating charges underground to collapse the mystery vault and retrieve the treasure once it was buried closer to the surface. But such plans were deemed too dangerous.

The pit had become a paradox. The deeper one dug, the farther the goal seemed to slip away. It mocked logic. Resisted force. It punished ambition.

At night, when the generators were quiet and the lanterns dimmed, men lay in their bunks staring at the beams above, listening to the faint trickle of seawater moving through the earth. Some swore they heard voices beneath the soil. Others said it was the island itself—breathing.

It was during these years that Oak Island’s identity shifted in the public imagination. It was no longer just a mystery—it had become a test. A living trial of man’s endurance, will, and belief. And it was only just beginning.

As the 1870s dawned, Oak Island stood as a quiet monument to failed ambition and costly obsession. The trees had been thinned, the shoreline scarred, and the Money Pit surrounded by makeshift structures, equipment remnants, and collapsed shafts. What had once been a natural wooded island was now the graveyard of engineering plans, abandoned machinery, and dreams.

But while some companies folded and investors walked away with heavy losses, others were just getting started. The mystery of Oak Island had taken firm hold of the public imagination. And for every man who left in defeat, there was another ready to take his place.

One of the key expeditions of this era was led by a group of businessmen and engineers who formed the Oak Island Association in the early-mid 1860s. They hoped to resume work on the Money Pit with improved drilling equipment and more capital. Learning from the failures of the Truro Company, they planned to construct more stable tunnels and increased pumping capabilities. However, their ambition would be met with all-too-familiar obstacles.

Shortly after breaking ground, the workers began experiencing erratic collapses. The main shaft began to give way under its own weight, and a secondary tunnel designed to skirt the flooded areas intersected with a natural cavern filled with water. In an attempt to reinforce their work, they installed timber cribbing—a lattice of wooden beams meant to prevent collapse. But it was no match for the pressurized floodwaters.

The deeper they dug, the more aggressive the water became, as if triggered by their actions. Each advancement seemed to provoke a counteraction. The Money Pit was not just flooding—it was resisting.

In 1866, a significant event occurred that would solidify Oak Island’s reputation as more than just a treasure site—it became a place of danger. As part of an attempt to clear debris and stabilize one of the flooded shafts, a boiler-powered pump was brought in. A platform was set, and teams worked around the clock.

Then, without warning, a chain reaction of collapses sent several men plummeting into the flooded earth. Two were killed instantly, their bodies never recovered. This tragedy brought the known death toll on Oak Island to four. The stories of the curse intensified.

Even newspapers that had previously treated Oak Island as a curious feature story began to adopt a more ominous tone. Articles described the pit as “insatiable,” a maw that devours fortune and flesh alike. Spiritualists and psychics claimed the island was haunted—by those who had buried the treasure or by those who had died looking for it.

Despite this darkening tone, exploration continued. In the late 1870s, yet another syndicate emerged, determined to locate the elusive vault believed to lie beneath the Money Pit. Their plan involved sinking a series of parallel shafts, hoping to bypass the booby-trap tunnel system and intercept the treasure from the side. It was an ambitious plan, and for a time, it seemed promising.

The men reached considerable depths without encountering significant flooding. Spirits were high. One afternoon, a test bore retrieved a sample of what was described as metallic material with a strange gleam, along with rotted wood and bits of what resembled leather. The crew was ecstatic. They believed they were close.

But on the following day, a muffled rumble shook the shaft. The timber supports groaned, and then the walls gave way. Water surged in like a living force, filling the newly dug shaft in a matter of minutes. A man named Edward Vaughn—descended from one of the original discoverers—was caught in the collapse. He survived, but barely, and he would never return to the island again.

These disasters weren’t just mechanical failures—they were psychological turning points. Men began to speak openly of a malevolent force guarding the island. Not metaphorically, but literally.

Dreams turned to nightmares. More than one laborer fled the island without collecting their pay, muttering about voices in the pit or the feeling of being watched. One chilling report came from a man named Frederick Nolan, an early surveyor who, during a mapping trip, claimed to find a series of boulders arranged in a strange pattern—like a cross, he said, too perfect to be natural. He believed it to be a marker, perhaps part of a coded map. But when he returned to the location weeks later, the stones had shifted or vanished.

Nolan would later go on to become a prominent figure in Oak Island’s history, but in the 1870s, he was dismissed as eccentric. Still, his observations lingered in the background of the island’s evolving legend.

During this time, a few explorers began to question the core assumption of treasure. What if the pit wasn’t meant to be discovered? What if it wasn’t guarding treasure at all, but something dangerous—a secret, a curse, a prison?

These fringe theories gained traction with each new failure, each collapse, each death. Books and periodicals began including Oak Island in collections of unexplained phenomena. It was placed alongside haunted castles, Bermuda Triangle accounts, and biblical mysteries. Some proposed it was a burial vault for ancient kings. Others thought it might be a depository of knowledge left by an earlier, advanced civilization.

The more absurd the theory, the more it seemed to match the absurd nature of the pit itself.