Based on the genealogical research of Clara Hollis-Hallett, which has it that the famous pilot James “Jemmy” Darrell was likely the son of James Darrell Sr, then that same researcher has determined that Anthony Darrell, born of James Darrell II with a slight chance of instead being the son of James Darrell Sr. This would mean Anthony Darrell was either the nephew or, in a vague possibility, the brother of Jemmy Darrell.

They were both men of the sea, whose paths more than likely crossed despite one living in St George’s and the other in Southampton. But whether or not they considered themselves as being of the same family is unknown.

Recently in a new book on Southampton Parish, published by the Bermuda National Trust as the tenth volume of Bermuda’s Architectural Heritage series, the outstanding life of Anthony Darrell who lived in Southampton was captioned as a whaler. In fact, what we now know of as the Whaler Inn and Whale Bay owned by the Fairmont Southampton gains its name from an actual business and property that was formerly owned by Anthony Darrell, who operated his whaling business from that spot, owning what was deeded as a half-acre of property.

The building was called the “Whale House” and was a 50ft by 20ft building where he kept all of his equipment. The Darrell descendants always held that they owned what they knew as Whale Bay, which becomes cloudy when one researches the War Act, which confiscated a lot of property in that area just before the turn of the 20th century.

Anthony purchased his own freedom in 1825, and by 1834 owned two ships, at least nine acres of property with two houses and a cow — which then was worth the equivalent of one acre of land — and the whaling business. However, it seems the real source of his wealth that allowed him to purchase the nine acres or more was through privateering.

Unlike Jemmy, Anthony had at least three known children, from which there are many living descendants, some bearing the name Darrell — and many by the names Wilson, Bean and Cooper. It is also possible that he had two others before emancipation; that research is ongoing.

The folklore running down the Darrell family is that they are descendants of pirates. Through stories told to me somewhere around 1990 by John Burland (deceased), in his family there was the legendary Nathaniel Darrell, who was an infamous pirate whose tale was that he split the booty 50:50 with his slaves.

Patching it all together, given that another White half-brother of Anthony would have been Benjamin Darrell, who owned Darrell’s Island, it became readily apparent that he was part of a network founded on the privateering business. Records of his furniture, which in the early 19th century was taxable, shows he had very expensive pieces that were more likely captured from a French vessel. In those grand old days, Darrell’s Island was the equivalent of Walmart or Macy’s, where all the pirating goods would be sold.

Anthony died in 1861 at the age of 84, placing his birth to be 1777. He would have been a young man in his prime when Jemmy — his brother or uncle — was nearing his peak. The British war against the French, stemming from the American Revolution — would have caused Anthony to be an asset during those years. Privateering was a dangerous business and Bermudian sailors were very good, aided with their sailing technology that could outmanoeuvre the rigged four-masted ships. With one gun mounted on the stern of the ship, they could sink a battleship ladened with multiple canons. They manoeuvred to the stern of the opposing ships and out of range of their guns.

Anthony was also a Friendly Society person who headed a lodge in Southampton. It seems the favourite mode of protest in the early 19th century was a march. There was an advertisement placed in The Royal Gazette informing of one such march in 1844. It was labelled as raising a “Red Flag” and as an invitation to join the march that would leave Caisey's Hill (now Vernon Temple AME). It is also understood that the former school called the “Brown School”, which later became Heron Bay School, was owned by him until it was sold in 1853 to Henry William King.

It appears that Anthony was a formidable person while he lived and, sadly, much of his assets were picked apart after he died. Fortunately, his White half-brother, Benjamin, stepped in and prevented the complete annihilation of his assets. This came up in the recent Commission of Inquiry into Historical Land Losses over two separate cases involving the Darrells and Wilsons.

The greatest tragedy, however, affected his daughter, Eliza Lusher, who as a nurse serviced the Royal Navy during the yellow fever pandemic of 1851 and 1856. She was promised payment for her nursing services by a Royal Navy officer who subsequently died. She therefore was not paid. Eliza petitioned the Government and lost in a parliamentary vote. Consequently, she faced pecuniary circumstances: she was land-rich but penny-poor. She died as a result of the same pandemic; her two daughters inherited her share of property but could not afford to hold on to it and succumbed to writs against her estate.

It is intriguing to note that Anthony Darrell and Jemmy Darrell, both legends of their time, were related as either brothers or nephew/uncle. For me and my family, it is a privilege to be a descendant of my great-great-great-grandfather, Anthony, and the great-great-great-great-nephew of Jemmy Darrell. I hope to honour their legacy.