On this week’s second episode of The Curse of Oak Island Season 5, the team examine a sea chest once owned by the fascinating Captain James Anderson.

The privateer (legal pirate) is believed to be the same “James Anderson” who once owned Lot 26 on Oak Island before selling it to former slave Samuel Ball — a familiar name to Oak Island fans — in 1788.

His chest has been passed down through his family for generations, and amazingly still contains historic documents including one showing he was a member of the Freemasons.

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But this is not the first time the chest has been investigated. Long-time researcher Scott Clarke, who has worked in the library, records management and archives field for just over 20 years, first became fascinated with the Oak Island mystery when he read about it in a newspaper in his home city of Toronto in 1993.

Later research led him to eventually discover that generations of his Nova Scotian “Archibald” relatives were among consecutive groups of treasure-hunters on the island throughout the 19th century.

In 2009, his investigations found him having the opportunity to meet one of James Anderson’s descendents, Bill Anderson, and actually examine the contents of the sea chest himself.

We spoke to Scott about his wide-ranging research into James Anderson and the Freemasons in Nova Scotia. Here he tells us the amazing story about what he found…

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❝I’ve been researching the Oak Island mystery for over 12 years now and have always been particularly interested in the Masonic connections to the island.

I’m sure the reason that so many high level Freemasons have been drawn to the island as searchers over the years is largely due to the early descriptions of the Money Pit being so reminiscent of certain Masonic teachings involving the existence of a physical sacred vault deep underground which contains priceless artifacts.

Generations of my own Nova Scotian relatives were also among the earliest treasure hunters on the island so you could say that the mystery is in my blood.

Around 1802-04 the search of the Money Pit continued when a group of men from Onslow, Nova Scotia took over. This group, known as the Onslow Company, was said to have been formed by Simeon Lynds, who is my first cousin, seven times removed and was led by Colonel Robert Archibald who is also my first cousin and Simeon’s Uncle.

Another cousin, Adams Archibald Tupper, was involved in three different Oak Island treasure hunting groups including the Truro Company from 1845-50, the Oak Island Association from 1863-65 and the Oak Island Treasure Company from 1893-97. In total I’ve discovered 14 relatives who were involved in various digs.

Over the years I’ve discovered some fascinating historical connections involving very high level Freemasons in Massachusetts as well as Nova Scotia who had connections to Oak Island prior to the 1795 discovery of the Money Pit. I also discovered a very early Masonic Lodge that once existed in Chester, Nova Scotia, very close to Oak Island.

This lodge was formed in December 1784 and of the 16 men who initially joined the lodge there were two with the name “James Anderson”. One was listed as being from Maryland and the other was from Scotland.

According to the 1791 Poll Tax records in Chester, one James Anderson was listed as being a Sailor and the other was listed as being a Mason (or operative stone mason).

Having previously done research into the earliest Oak Island lot owners with other researchers, I knew that a “James Anderson” was also one of the earliest lot owners on Oak Island in 1785.

In 2009 I had been doing some online researching into James Anderson and came across another researcher named Pat Hagan who was also looking for information about James Anderson from Chester, Nova Scotia, as he was a direct descendant of his.

Pat mentioned that another of his Nova Scotia relatives named Bill Anderson actually had an old sea chest that belonged to James Anderson and it contained an original Masonic document given to James in 1791. At that time I told Pat that I had quite a bit of information about James’s Masonic lodge in Chester and told him that his “James Anderson” may have been one of the earliest lot owners on the famous Oak Island.

I told Pat that I was actually going to be visiting Oak Island within a few months and he graciously offered to arrange for me to visit with Bill Anderson while I was in Nova Scotia to see the sea chest and Masonic document for myself. As you can see from the photos there is a smaller chest within the large chest.

Aside from the Masonic document from 1791 there is also James’ original membership certificate to the New York Marine Society from 1781. There’s also documentation to show that James had come to Nova Scotia from Maryland so this confirmed which of the two men he was.

The census from that time stated that one of the James Andersons was a Sea Captain and I also read that he was likely a privateer (or legal pirate).

More recently Pat has continued to research the life of James Anderson and teamed up with another descendant of James named Diane Boumenot who has done extensive genealogical research and created a series of interesting blogs about James and his fascinating exploits during the American Revolution.

Essentially James lived in Baltimore, Maryland, in the 1770s and when the American Revolution started he originally sided with the Rebels and was given command of a ship called the Baltimore.

Soon after however he changed sides and became commander of a Loyalist (British) ship. At some point in Maryland he also became a Freemason. He was eventually captured by Rebel forces and recommended to be charged with high treason (in a letter sent to future President Thomas Jefferson) but somehow he was set free and eventually made his way to Nova Scotia.

There were many Freemasons on both sides of the conflict and I believe that his involvement in Freemasonry saved his life.

I’ve still not been able to determine with certainly which “James Anderson” owned the lot on Oak Island. The lot was #26 and he owned this for about three years before selling it to Samuel Ball in November 1788. Samuel of course will be familiar to viewers of the Curse of Oak Island show.

According to James’s Masonic document he died in the West Indies in July 1796. Sadly this would have been only two months before his daughter Ann was born. James would have likely been around 48 years old when he died.

Another document, which we were previously shown being examined in the trailers, has to do with James Anderson during the American Revolution, and is signed by Robert Christie Junior who was the Sheriff of Baltimore in 1776.

Clearly the producers of The Curse of Oak Island are banking on the likelihood that the James Anderson who owned the sea chest and who was a privateer (legal pirate) during the American Revolution was also the same man who owned the lot on Oak Island.

It’s certainly quite possible and it’s also possible that James resumed his activities of privateering and smuggling once in Nova Scotia. One has to wonder why he was in the West Indies in 1796 and where else he may have been over the 12 years that he resided in Nova Scotia? That being said, his Oak Island lot would have been a perfect place to bury any ill-gotten gains.

Incidentally, James Anderson was not the only interesting and controversial member of the Chester Masonic lodge prior to 1795 and he was not the only lodge member to own property on Oak Island…but that’s another story.❞

Anyone who wants to get in touch with Scott with any questions or for further information about his research can do so by emailing him at scottclarke416 (AT) gmail (DOT) com.

The Curse of Oak Island airs Tuesdays at 9/8c on History.