The Forgotten Princess of Newfoundland

The Legend of Sheila O’Connor and Gilbert Pike

Let’s talk about a story that sounds like it was ripped straight from the pages of a swashbuckling historical novel—only, this one has been passed down through centuries of Newfoundland folklore. A tale of royalty, exile, and piracy, intertwined with whispers of a mysterious tomb hidden in the overgrown woods of Carbonear. But how much of it is true, and how much is just another romanticized legend?

The Mysterious Sheila O’Connor: Princess in Exile?

According to the story, Sheila O’Connor was an Irish princess, the daughter of Sir Hugh O’Connor. Her family, embroiled in political conflict in Ireland, supposedly sent her into hiding amidst the chaos of a struggle for the throne. From there, the details get murky. Some versions claim she fled to France, a common refuge for Irish nobility facing English persecution. Others say she was captured at sea, leading us to the most intriguing part of this legend: pirates.

A Pirate Abduction or a Rescue?

If Sheila O’Connor truly existed, her journey to Newfoundland was anything but ordinary. Enter Peter Easton, the notorious English privateer turned pirate, who was active in the early 1600s. He roamed the Atlantic, raiding ships and striking fear into settlers along the coast. One version of the story claims Easton captured Sheila—perhaps during a raid on a vessel bound for safety. But did he truly take her as a prisoner, or was she “rescued” from an even worse fate?

Peter Easton

This is where another name emerges: Gilbert Pike.

Gilbert Pike: Pirate, Settler, Husband

While no definitive records confirm Gilbert Pike’s role in Easton’s fleet, legend suggests he was one of Easton’s men—or at the very least, a fellow pirate. The story goes that Sheila and Gilbert fell in love (or she was given to him as a “prize,” depending on who tells it). They eventually settled in Newfoundland, specifically in Carbonear or nearby Mosquito (now known as Bristol’s Hope). The town was one of the earliest Irish-influenced settlements in the New World, making it a fitting place for an exiled princess to start anew.

Sheila NaGeira, as she’s often called in folklore, is said to have been deeply respected by the Irish community there. Some claim she was a healer, others say she used her noble upbringing to bring structure and leadership to the settlers. Whether she was truly an Irish princess or simply a woman whose story grew grander with each retelling, one thing is certain: her name lived on.