The Oak Island Mystery: 200 Years of Buried Secrets (Part 3)

As the 20th century dawned, Oak Island stood weathered but unyielding. Dozens of shafts scarred the earth like veins. Rusted equipment lay tangled near the shoreline, and the haunting silence of failure blanketed the island like fog. The island had resisted everything—hope, manpower, strategy, and brute force—but it had not been forgotten.

In fact, the new century brought something the 19th could not: innovation. While steam pumps and cribbing had failed in the past, the next wave of treasure hunters believed that modern engineering would finally conquer the Money Pit. The world was changing. Skyscrapers pierced the sky in New York. Ships crossed the Atlantic in record time. Electricity hummed through cities once ruled by candlelight. Why couldn’t the same ingenuity finally unlock Oak Island’s secret?

In the early 1900s, a group led by William Chappell—a contractor with a mind for design and a passion for history—formed a new syndicate and began operations on the island. Chappell wasn’t a wild dreamer. He was careful, methodical, and invested in facts. He reviewed every previous expedition’s notes and maps and approached the dig with renewed logic.

His team didn’t immediately return to the original Money Pit, which was now too unstable to excavate. Instead, they focused on areas nearby, hoping to intercept the elusive treasure vault from a side angle. It was a new tactic, rooted in the theory that the real treasure chamber had been missed entirely due to earlier collapses and water intrusion.

Their strategy paid off—at least initially. In 1909, while boring near what was believed to be the original pit location, Chappell’s drill struck something hard at around 160 feet. What came up in the core sample stunned the crew: a piece of cement, followed by a small iron artifact resembling a hand-forged nail, and a fragment of parchment. The writing on the parchment appeared faded but deliberate—a single letter, possibly a “V” or “W.”

To outsiders, this may have seemed like little more than debris. But to those who had studied Oak Island for years, it was monumental: cement, iron, and parchment—all in a single sample buried more than 150 feet underground. It was proof—however faint—of something man-made, something hidden, something intentional.

But again, just as excitement began to rise, the island retaliated. Flooding returned. Boreholes collapsed. Despite their best efforts, the team was unable to recover anything else from the same area. The elusive vault had slipped through their fingers once more.

Yet Chappell’s discoveries would leave a lasting impression—so much so that they caught the attention of a young man named Franklin Delano Roosevelt, then just 27 years old. Years before he would become President of the United States, Roosevelt was fascinated by Oak Island. The mystery, the history, and the enduring human obsession all captivated him.

He became part of a financing syndicate with ties to Chappell’s operation and even visited the island personally. Though he never returned, he followed developments on Oak Island for decades afterward, reportedly requesting updates from associates while he was in the White House.

The Roosevelt connection was just one example of how Oak Island’s legend had begun to stretch beyond Nova Scotia. It had entered the public consciousness in a new way. This wasn’t just a local treasure hunt anymore—it was a national fascination.

Encouraged by Chappell’s partial success, another syndicate formed: the Old Gold Salvage and Wrecking Company. This group, too, included Roosevelt and other investors who pooled funds to resume digging. Their method was more aggressive—larger shafts, heavier machinery, and increased use of steam pumps.

But Oak Island held firm. As shafts collapsed and financial losses mounted, even Roosevelt’s enthusiasm waned. The 1910s passed with little success. World War I shifted global attention, and Oak Island sat mostly dormant for the next decade.

But the 1920s brought new life. A man named William Blair formed yet another company—the Oak Island Treasure Company—and resumed boring near the Money Pit. Blair believed he could improve upon past failures by incorporating updated drill rigs and concrete reinforcements.

His team managed to extract samples similar to those recovered in 1909: traces of cement, small wood shavings, and the ever-elusive fragments of parchment. They pressed deeper.

Then a new mystery emerged.

At roughly 170 feet, a drill struck a cavity—a hollow space. As the drill bit descended into it, it made several soft contacts. The team believed it had struck chests—possibly multiple—resting in a sealed stone room. Echo tests and pressure readings suggested an open chamber roughly six feet tall, with hard walls and soft materials stacked within.

It was the closest anyone had come to confirming the presence of a vault.

But what came next was all too familiar.

As workers prepared to widen the borehole and lower a retrieval device, disaster struck. Water began to rise from below—not from Smith’s Cove, but from deeper underground. It surged into the borehole and caused a total collapse. The chamber was lost again.

Some claimed that the chamber had been deliberately flooded—a second trap set to destroy it if tampered with. Others believed it had already decayed naturally, its contents destroyed by centuries underground. Either way, the opportunity was gone.

By the end of the 1920s, Oak Island had seen over a dozen separate companies, dozens of shafts, and hundreds of thousands of dollars spent—and not one ounce of treasure had been retrieved.

Still, they came.

The 1930s brought with it the era of deep core drilling and seismic analysis. These technologies—though in their infancy—offered new hope. Teams began using soundwave equipment to measure anomalies underground. While the results were inconclusive, many pointed to areas of unnatural density that could indicate chambers, vaults, or metallic contents.

Once again, drills were deployed. Once again, the evidence was promising—a cavity here, a strange metal resonance there. But the pit remained sealed in its stubborn silence.

Then came the Great Depression.

As financial markets crashed and investment dried up across the globe, Oak Island grew quiet. Work slowed to a crawl, and the mystery returned to sleep beneath the earth. The once-bustling campgrounds were empty. Machinery rusted in the salt air. The Money Pit was filled with nothing but silence and memory.

But not everyone had given up.

In the 1930s, a retired naval engineer named Gilbert Hedden visited the island after reading about it in a magazine. Unlike many who came before, Hedden wasn’t seeking adventure or fame. He was a man of logic—and what he read fascinated him.

He pored over every diagram and journal he could find. Something about the measurements, the artifacts, and the engineering convinced him the island was hiding something real. He bought land on Oak Island. He purchased equipment. He dug.

In 1936, Hedden’s team uncovered a stone tunnel running east to west, roughly 100 feet inland from Smith’s Cove. It was dry—a rarity—and carefully laid with flat stones. Some believed it could be a feeder tunnel, or perhaps a transport route for moving items between shafts.

Hedden believed he was on the verge of a breakthrough. But just as before, a collapse followed. The tunnel caved in. A secondary shaft filled with water. Hedden, like so many before, ran out of funds before he could finish his work.

Yet his legacy lingered. He had brought methodical engineering back to Oak Island. He had reminded the world that there was still more to be found. And perhaps most importantly, he reignited the obsession for a new generation.

As the 1940s arrived and war once again consumed the world’s attention, Oak Island returned to its natural state—quiet, forested, and undisturbed. But beneath its soil, the legend remained intact and patient.

By 1950, the island had seen half a century of technological advancement—and half a century of failure. The tools had changed. The men had changed. The outcome had not. The Money Pit remained undefeated.

The 1930s brought a new wave of ambition to Oak Island. Despite decades of disappointment and financial ruin, the legend of the Money Pit remained alive in the hearts of dreamers, engineers, and wealthy investors. The belief that the treasure was real—and perhaps closer than ever to being discovered—fueled yet another chapter in this relentless saga.

Among the new generation of seekers was a man named Gilbert Hedden, steel industrialist and former superintendent of public works in New Jersey. He first encountered the Oak Island story in a 1928 edition of the New York Times Magazine. The article recounted the history of the island’s mysterious shafts, booby trap tunnels, and failed excavations.

Hedden—a practical and educated man—was immediately intrigued. He immersed himself in research, collecting every document, map, and article he could find. The more he read, the more obsessed he became.

Unlike some who had come before him, Hedden had the financial means to take immediate action. In 1934, he purchased a significant portion of Oak Island and assembled a team to begin a new round of exploration.

Hedden’s approach was unique for the time. He emphasized planning, documentation, and caution. His team used advanced boring techniques newly available from mining industries and began investigating areas adjacent to the original Money Pit. They also conducted one of the first comprehensive surveys of Smith’s Cove, suspecting it still held clues about the ingenious flood tunnel system.

What they found was compelling.

At Smith’s Cove, Hedden’s workers uncovered a U-shaped wooden structure buried beneath layers of clay and beach gravel. Carefully excavated, it revealed evidence of purposeful construction—interlocked timbers, layered platforms, and traces of coconut fiber—once again confirming the presence of non-native materials.

These discoveries reinforced the theory that Smith’s Cove was indeed the source of the flooding system engineered to protect whatever lay deep in the Money Pit.

Excited by these findings, Hedden hired divers to investigate underwater passages. Their work, though limited by the technology of the time, confirmed the presence of subterranean channels connecting the sea to the island’s interior. This added weight to the belief that the island had been engineered with remarkable sophistication.

Hedden also conducted drilling operations, focusing on several promising sites near the Money Pit. While no treasure was recovered, core samples again revealed oak wood, cement-like material, and soft metal shavings. The story of a hidden vault beneath the island refused to die.

Even more curiously, Hedden found what he believed to be a carved stone with strange symbols etched into its surface. Some theorists connected this stone to the infamous inscribed tablet said to have been found by the Truro Company in the 1800s, which had vanished decades earlier. Although its authenticity was never confirmed, it became yet another thread in the growing tapestry of clues.

But as with every expedition before his, Hedden’s work was met with obstacles. Heavy rains flooded shafts. Equipment failed. Funds began to dwindle.

Though he had made progress in mapping the island and confirming several earlier discoveries, he was ultimately unable to reach the chamber he believed was real. Still, his efforts were not in vain. He had reignited interest in the mystery and brought new legitimacy to the legend through methodical work and professional documentation.

Even as he withdrew from active exploration in 1939, Hedden’s influence lingered. His records would guide future treasure hunters.