In Part 1 of this series, we covered how the Oak Island legend began, a suspicious depression in the ground, three names now inseparable from Nova Scotia folklore, and a shaft that flooded the moment early diggers got close to whatever lay at the bottom. What followed over the next 170 years is one of the strangest patterns in the history of treasure hunting: company after company arriving with more money, more equipment, and more confidence than the last, only to run into the same wall and, on one catastrophic day in 1965, to pay for it with their lives.
What Are the Oak Island Flood Tunnels?
The core mystery of Oak Island isn't really the pit itself, it's what keeps filling it with water. Beginning with the Truro Company's excavation in 1849 and 1850, searchers came to believe the Money Pit was connected to the nearby shoreline at Smith's Cove by a network of engineered drains, sometimes described as "finger drains," designed to funnel seawater directly into the shaft the moment it was dug past a certain depth. The theory held that whoever built the original pit had also built its defense system, timed to trigger automatically no matter how carefully searchers tried to avoid it.
It's a genuinely compelling piece of speculative engineering and also one of the most contested claims in the entire case. Some searchers over the decades reported finding physical evidence of constructed drains at Smith's Cove, including layers of coconut fiber believed to have functioned as a natural filter. Others, including later scientific investigators, found the physical evidence far less convincing than the legend suggests, a tension this series will return to directly in Part 3.
How Did the Search Turn Deadly?
The first fatality came in 1861, during an attempt by the Oak Island Association to succeed where the Truro Company had failed. While pumping water from the shaft, a boiler on one of the steam pumps burst, killing one worker. That same excavation saw the bottom of the pit collapse into what may have been a natural cavity beneath the shaft, whether that collapse was a structural failure, a natural sinkhole, or evidence of the treasure chamber itself giving way has never been resolved. The Oak Island Association ran out of money and abandoned the site a few years later, worn down by the same flooding that had defeated every company before it.
The 1866 Eldorado Company, later known as the Halifax Company, focused specifically on stopping the suspected flood tunnels at their source, attempting to seal off Smith's Cove directly. It didn't work; the tides broke through regardless, and the company gave up in 1867 having spent a considerable sum with nothing to show for it.
Progress, of a sort, resumed in the 1890s under Frederick Blair's Oak Island Treasure Company, which became one of the most consequential expeditions in the island's history. Drilling operations recovered a tiny fragment of what appeared to be sheepskin parchment bearing a few handwritten letters in India ink, a discovery searchers found tantalizing precisely because it suggested the buried structure held something worth writing on, not just raw treasure. Blair's team also confirmed what they believed was a second flood tunnel, this one running from the island's south shore rather than Smith's Cove, meaning that even if searchers found and blocked the first tunnel, a second one had apparently been built to keep the pit flooded regardless. It was during this same period, in March 1897, that a worker named Maynard Kaiser fell to his death in one of the shafts, becoming the excavation's second fatality.
Blair's company ran out of money in 1900, but Blair himself never gave up on the mystery. He spent the next several decades securing treasure rights and advising the searchers who came after him, remaining personally convinced the treasure was real until his death in 1951, a fifty-year commitment to a mystery he never got to see solved.
What Happened in 1965?
The deadliest chapter of the Oak Island story unfolded across a single day in August 1965. Robert Restall, who had been excavating the site with his family since 1959, was attempting to seal what his team believed was an old storm drain at Smith's Cove. While working in a shaft roughly 27 feet deep, Restall was suddenly overcome by hydrogen sulfide gas, an invisible and highly toxic byproduct of decomposing organic material that can accumulate in confined excavations. His son Bobbie climbed down to help him and was overcome by the same fumes within moments. Two more men, Karl Graeser and Cyril Hiltz, rushed in to attempt a rescue and suffered the identical fate. A fifth man, Andy DeMont, was pulled out alive by a bystander who lowered himself into the shaft on a rope; Restall, his son, Graeser, and Hiltz all died.
That single afternoon accounts for four of the six deaths connected to Oak Island across its entire 230-year history, and it remains the clearest evidence that whatever draws people to this island, the danger involved has never been exaggerated for effect. It's also the origin of the island's grimmest piece of folklore, the belief that the treasure won't surface until seven men have died searching for it, a number the 1965 tragedy pushed uncomfortably close to.
Did Later Searchers Ever Find Solid Evidence?
Following the Restall tragedy, geologist Robert Dunfield leased the site and brought in dramatically more aggressive equipment than any previous searcher, including a 70-ton crane, to excavate a massive open pit rather than a narrow shaft. Dunfield's dig destroyed much of the original shaft's structure and context in the process, and to this day, the precise location of the true original Money Pit is no longer known with certainty, one of the more frustrating ironies in a case already full of them. Dunfield himself examined the surrounding walls closely during his excavation and reported finding no physical evidence of the engineered flood tunnels that generations of searchers had built their entire theory around.
The only rigorous outside scientific study of the site came decades later, in 1995, when researchers from the Woods Hole Oceanographic Institution examined the area and reached no conclusions supporting the treasure hypothesis. That result hasn't stopped the search. Dan Blankenship partnered with businessman David Tobias to form Triton Alliance in 1969, continuing excavation work for decades, and in 2006, brothers Rick and Marty Lagina purchased a majority stake in the site, the search that continues, very publicly, to this day.
In the next part of this series, we'll dig into the theories themselves: who might have actually built the original shaft, what they might have buried there, and how well each competing explanation, from pirate gold to the Knights Templar, actually survives contact with everything covered so far.
Frequently Asked Questions
What are the Oak Island flood tunnels? The flood tunnels are a theorized network of engineered drains believed to connect the Money Pit to the nearby shoreline, designed to flood the shaft with seawater if it's dug past a certain depth. Their existence remains debated among researchers.
How many people have died on Oak Island, and how? Six people have died during Oak Island excavations. The first died in an 1861 boiler explosion, a second, Maynard Kaiser, fell into a shaft in 1897, and four more, including Robert Restall and his son, died from hydrogen sulfide gas exposure in a single incident in 1965.
What happened to the Restall family on Oak Island? In August 1965, Robert Restall was overcome by toxic gas while excavating a shaft. His son and two coworkers died attempting to rescue him, resulting in four deaths in a single afternoon, the deadliest incident in the island's history.
Has anyone found scientific proof of treasure on Oak Island? No. Geologist Robert Dunfield found no physical evidence of the theorized flood tunnels during his 1965 excavation, and a 1995 study by the Woods Hole Oceanographic Institution reached no conclusions supporting the existence of buried treasure at the site.
Who is currently searching Oak Island? Brothers Rick and Marty Lagina purchased a majority stake in the site in 2006 and continue excavation efforts today, documented in the History Channel series The Curse of Oak Island, which has run for over a decade without a confirmed discovery.
Read the Full Oak Island Investigation Series
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