Many persons have heard of Captain Jimmy Darrell, whose his excellent work with the British Royal Navy and role as a sea captain navigating the treacherous channels of Bermuda earned him his freedom and ownership of property. Virtually no one has heard of or knows the name of Anthony Darrell, who was also a pilot, seaman and sailor — but in the private arena.

Here, I’m going to bring to life, hopefully, the beginnings of a story about a man, a personality who was also once a slave and who purchased his own freedom — becoming perhaps the richest Black man in Southampton and, until proved differently, the wealthiest Black man in Bermuda at the time of emancipation.

Anthony Darrell, born 1777 a slave and son of James Darrell II. I am yet to uncover his mother’s details, but that information I am sure will be revealed.

The reason for bringing this soul of Anthony Darrell to life is because most of history tends to record enslaved Africans as statistics rather than as people, and they are characterised or determined by the role they played as slaves. In reality, these were real persons with all the sentiments of any human. They, in spite of the circumstances of slavery, had to figure how to better their lives. Darrell had endured being a slave for 23 years during the 18th century and after 48 years of age on this earth in 1825, he purchased his own manumission (freedom).

Folklore in my family had always informed his descendants that we had come from pirates. I had learnt also through the folklore of John Burland, who had an ancestor whom they referred to as their "infamous" Captain Nathaniel Darrell. His folklore says he shared the booty from his privateering escapades 50/50 with his slaves. That was his direct transmission of folklore, which matched or at least answered a big question I had about how Anthony purchased his freedom in 1825, and then how he ended up with so much property by 1834.

With a little genealogical digging, I was able to uncover that Anthony had some White half--brothers who were very powerful in their own right, and who from a family including the likes of John S. Darrell were engaged in maritime pursuits, including privateering.

Anthony owned at least two boats, one of which he called his “large boat”. I could only ascertain that for a good portion of his younger years, he along with persons such as the infamous Captain Nathaniel Darrell was in some kind of partnership in the pirating business and did very well. Travelling on those excursions to the Caribbean and the East Coast of the United States had to be an enriching experience in more ways than just material. The maritime trade helped his intellectual development, making him aware of circumstances and trends happening in the entire Western hemisphere.

Anthony got married to Lettice Jones with the permission of her slave master. He had four children — two sons and two daughters — and later two granddaughters mentioned in his will, and a grandson born after he wrote his will. Anthony could read and write, and had posted notices in the newspapers.

He began a friendly society and was very active. His own friendly society was also active with other friendly societies and led some form of protest in 1938 when they raised the red flag one Sunday afternoon and marched from what was then Casey’s Hill (located where Lightbourne’s shop was, opposite Vernon Temple Church) over to the Turtle’s Hill area along with the Good Intenders Society.

Anthony was a leader and influential man in Southampton post-emancipation. His legacy as a leader obviously inspired his daughter, Elizabeth, who married a Lusher and was noted in this newspaper by Cecille Snaith-Simmons for her “unrewarded service” and sacrifice as a nurse for soldiers and others during the yellow fever epidemic of 1853. She later succumbed to the illness herself in 1859.

Anthony also had a very large whaling business called Southampton Whaling Company, which had grown to be a significant business. He had a building on the South Shore where all his whaling equipment was held and from where the industry was run. It is more likely what we know now as Cross Bay — or, to some, Sinky Bay — was probably part of his estate, which he left as an inheritance to his granddaughter, Ellen Lavinia Lusher, who married a Wilson.

He owned property stretching from Heron Bay (now Heron Bay School) all the way to what is known as Sunnyside Park, plus land nearer to Warwick Camp. Some of the land, forming what later became Heron Bay School, was dived off and sold and other significant pieces lost through litigation against some of his heirs. But significant pieces remained.

Anthony was respected by many, including his own White family, no doubt considered by them to be just as crucial and infamous as Captain Nathaniel. He had a young White brother named Benjamin born around 1825 when Anthony was very much his senior and, perhaps, hero.

Benjamin became a very successful merchant and owned what we know as Darrell’s Island. One can do the calculus and figure Benjamin, who became wealthy in his own right in owning Darrell’s Island as a port in the midst of a privateering famiiy including Anthony. Darrell’s Island would have been used when the central port for Bermuda was formerly the Paget Port before the formation of Hamilton, which was new at the time and places such as Salt Kettle were still active.

As Benjamin got older, there is evidence of his activities weaving in and out of that of his older Black brother, Anthony, and later with his descendants on property deals in Southampton. Anthony was fortunate to have lived to a good age of 84, dying in 1861. However, tragedy struck much of his family in the latter portion of the 19th century and many of his descendants died at younger ages in relative proximity because of epidemics, to which mariners were particularly susceptible. Hence, sadly for too many of them, aside from intemperance, the autopsy listed consumption (tuberculosis) as the cause of death.

Yes, many of these 19th-century men of Anthony's family, had written on their death certificate “intemperate lifestyle” and of course, what else? These were rugged seamen of Southampton or Port Royal, as it was known then, as a port town replete with bars and all that goes with ports. Waterlot Inn is only one such surviving establishment. But these folks were seafarers; they did not need to depend on the bars, they had direct access to rum, straight from the sugar mills and plantations in the Caribbean — and I’m quite sure they carried a barrel or two on many of their return trips from the islands, and Newfoundland and Nova Scotia, which were known for rum.

Anthony Darrell was a legend during his time, but through fate and circumstance of epidemics, his memory has been removed from history. His progeny, this present generation — some of whom have lived on property that was once part of his vast estate — for most do not know of this once slave and extraordinary entrepreneur/ancestor of theirs who created that wealth they live on.

The unfortunate deaths of many of his immediate descendants caused a gap where his memory was discontinued. My hope is to bring his legacy back to life.