It looks like Captain James Anderson was a privateer at the beginning of the American Revolution. In case you’re not familiar with the term, a privateer is a person empowered by the government to predate upon foreign shipping, therefore making them a useful supplement to the government’s naval power.
At the start of the revolution, Captain James Anderson signed up with the rebel cause. He started out as a lieutenant on someone else’s ship and managed to have his own eventually. Nonetheless, he sailed into New York, where he became a loyalist privateer.
Furthermore, he got captured by the rebels, which brought his life into danger, as there was a possibility that he could be executed. After all, he had pledged loyalty to the Americans before changing sides, which means that he had committed a huge act of treason. Still, he wasn’t executed, and he and his family settled in Chester, Nova Scotia, after the American Revolution.
A sea chest owned by Captain James Anderson that was afterward passed down to his descendants and was recently examined by the people behind The Curse of Oak Island. Namely, it seems that the TV show has a lot of things to hope for regarding this matter.
Captain James Anderson was a member of a Masonic Lodge in Nova Scotia, according to a certificate for his membership which has survived until today. Next, he was a privateer for some time, which is a legal sort of pirate as he had the blessing of the government. Last, Chester is located near Nova Scotia, which means that he may be the James Anderson who was one of the earliest lot owners on Oak Island. All in all, it is evident that the people behind The Curse of Oak Island are trying to connect Captain James Anderson with the supposed treasure buried in the Money Pit, but since everything is uncertain at this point, we all have to wait and see what lies around the corner.