The Men Behind the Boats

Historical Figures Page

This page highlights the contributions that Black Bermudian sailors made to the evolution of sailing in Bermuda and paints a picture of resilience.  Today, sailing is a sport that is welcomed by all.


In 1603 Diego Ramirez, captain of a Spanish galleon found himself shipwrecked on the island by a storm. It stands to reason that since the land was unfamiliar to Ramirez and that he lived at a time when there were so many superstitions to explain things in nature, Ramirez would send the slave, Venturilla to do the exploring. Venturilla’s encounter with Bermuda’s endemic birds, the cahow, was no different than the encounter that other survivors encountered. Unlike today, the birds were not facing extinction and were multitudinous – so much so that the volume of sound was so cacophonous that the superstitious explanation of the crew members at the time could only label it as one thing – the cry of the Devil. The known moniker of the island came to be “The Devil’s Isles” as it was thought that the Devil took up residency on this island – a  silly notion today but a very serious prospect back then.

Here is the actual account of Venturilla’s experience with the cahows according to Captain Ramirez:

One Venturilla, a negro, was sent ashore with lantern and axe  to cut a  piece of cedar. The moment he landed and entered  the bush, he set up such a yell, that I shouted: The devil’s  carrying off the negro! Everybody ashore! The men jumped  into a boat and rushed to the spot, where the negro was brandishing his fists against the birds (cahows) and mingling his yells with theirs. The birds, meanwhile, attracted by the light, dashed against him, so that he could not keep clear of them even with a club. Neither could the men of the relief party. More than 500 birds were brought off to the ship that night. (Rosemary Jones, Bermuda Five Centuries p.19)

Venturilla’s encounter with the cahows (seabirds) was fortuitous as the food supply on the damaged boat was dwindling. The crew feasted on the clubbed cahows for several days. Venturilla’s stay in Bermuda was a brief one. The crew spent three weeks on the island repairing the damaged ship and then continued their journey. Nothing more was heard of Venturilla. His name lives on in one of Bermuda’s ferry boats.

James Jemmy Darrell

Born 1749 – April 12, 1815

In preparation for the construction of the Dockyard, British surveyor Lt. Thomas Hurd was sent to Bermuda to carry out the first comprehensive marine survey of the island.  James Darrell, Jacob Pitcarn and Tom Bean were among the slaves who assisted Hurd with his survey. It is likely they were chosen for their skill as pilots and extensive knowledge of the island’s bays, inlets and coastline because piloting was an occupation that blacks dominated from Bermuda’s earliest days.

They sounded the depths using lead lines tied at regular intervals with strips of calico, serge and lether.

While carrying out his survey, Hurd marked several channels at the east end of the island to allow naval ships to navigate the treacherous reefs and enter protected anchorages without incident. That was a departure from previous access points—usually ships entered Bermuda from the west end or the south shore into Castle Harbour.

James “Jemmy” Darrell appointed King’s Pilot in 1795 – On May 17, 1795, two years after Hurd began his survey, Darrell manoeuvred Rear Admiral George Murray’s 74-gun ship HMS Resolution into a deep anchorage—now known as Murray’s Anchorage—on the North Shore near Tobacco Bay, St. George’s.  It was a feat requiring great skill and Darrell came through with flying colours. He impressed everyone from onlookers to Murray, who wrote Governor James Craufurd the same day, showering Darrell with praise.  Murray described Darrell as having “great merit for his ability and steadfastedness”. He recommended that the government purchase Darrell’s freedom as an example to others who might also be inspired to become King’s pilots. Darrell, along with Jacob Pitcarn and another slave, were appointed the first King’s pilots in 1795. Their main responsibility was to pilot British naval ships through the reefs.

James “Jemmy” Darrell granted freedom – Murray’s recommendation that Darrell be freed was approved by the Governor’s Council on December 1, 1795. The Governor paid Joseph Laborn 150 pounds for Darrell, who was officially granted his freedom on March 1, 1796.  The change in status brought Darrell some benefits, but not total freedom. He could pocket his earnings, but could not serve on a jury or give testimony in court. In addition, the social climate for free blacks had worsened as a result the 1791 Haitian Revolution, which had struck fear in the hearts of slave owners everywhere. Free blacks were targeted because they were believed to be the ringleaders of slave uprisings.

Stephen Benjamin Richardson

(1800 – 1879)

There are no documented photos of Stephen Benjamin Richardson.  Pictured is Pilot James Butterfield Richardson, son of Stephen Benjamin Richardson who also became a pilot

STEPHEN BENJAMIN RICHARDSON 1800-1879 born an enslaved man always had a desire to become a pilot. An alert and intelligent young man he quickly advanced in his chosen career. He saved enough to purchase his freedom and in later years the freedom of his wife for 30 pounds.He was one of 38 free blacks who signed a petition addressed to the government for the removal of disabilities under which free blacks and free people of colour had to labour.He was classed a hero when he saved a young woman from a near fatal accident in 1838.Stephen was issued a certificate of competence by captain by Captain Edward Franklin of the Royal mail Steam ship Tweed after he piloted the vessel out of Castle Harbour.

Stephen Richardson was  able to purchase property in St. Georges’ near the Golf course in 1847. He later built his home on this land and named it “Northside”. He was one of 563 signatures who petitioned against the importation of farm labour. He was classed as one of the most skillful branch pilots of his time and for many years held the position of Pilot examiner.  Both Jemmy Darrell and Stephen Richardson homes have been selected to be put on the Bermuda Foundation African Diaspora Trail.

His Brass Binoculars can be found at National Museum.  “because the binoculars have passed down for generations in the same family, they carry the family memory and history with them, and this connects us to the lived experience of the past. The binoculars belonged to Branch Pilot Stephen Benjamin Richardson and were donated to the Museum by his descendants. Richardson lived in St. George’s and was born in 1801, he was a highly skilled branch pilot and his binoculars were used when keeping an eye out for incoming vessels. On his death in 1879, Pilot Richardson was described as “the oldest and one of the most skillful Branch Pilots of these Islands”. Three of his sons became pilots and these binoculars were passed to his son Pilot George Richardson.”

Charles ‘Roach’ Ratteray

circa 1800-August 24, 1872

Charles Roach Ratteray won respect and renown, working as a west-end ship’s carpenter, boat builder and trader during the post-Emancipation era.

He built skiffs and schooners, which he loaded up with onions and potatoes and sailed to the Caribbean and the US east coast, becoming a wealthy property owner in the process.

He was one of several men who were instrumental in bringing the British Methodist Episcopal Church (BME) — the forerunner of the African Methodist Church (AME) — to Bermuda.

The Ratteray name originated with him and his legacy looms large in present-day Bermuda through the contributions of his descendants.


Born in Nassau, Bahamas, he was brought to Bermuda by his mother as an infant. When his mother died, he was raised in Somerset by two white spinsters, who lavished him with love. He learned to read and write and was trained as a ship’s carpenter.

During the first 25 years after Emancipation in 1834, shipbuilding was on the decline but still thriving, according to historian Dr. Kenneth Robinson. Ratteray was one of scores of black Bermudians who made their living in the industry.

Ratteray built his first vessel, a sailboat, when he was in his early teens, followed by a sloop, Little Morning Star. While primarily a ship builder, he went to sea on his ships, packing their holds with onions, potatoes and other fresh produce to sell in Caribbean and US east coast ports.


He became so established that he was referred to as “the celebrated builder” in the media.
Newspaper articles and ads attest to his prominence and prowess. In December 1851, he took out an advertisement in The Royal Gazette, offering his sloop Morning Star for sale.

Morning Star had made three trips to the Caribbean and back, could carry 15,000 pounds of onions “comfortably”, and “for speed she stands A.1. among any of her class,” the ad said. He also offered liberal financing to the purchaser. It is not known whether he found a buyer for that ship.

In1855, Ratteray and his son George built the 51-foot schooner Rose of Sharon. They launched it on May 15 at Herman’s Bay, Somerset before a large crowd and to live music played by the Somerset Brass Band. Father and son were praised in the newspaper report for their “industry, skill and perseverance” and for the inventive way they built it.

In an article in The Royal Gazette in May 2000, descendant Ellsworth Ratteray explained: “They made a jetty out of rock that they dug from the cliff. It went from the beach into the sea.
“They built their ship on this temporary jetty and when she was ready to be launched, they dug out the rocks and let her float off the tide.”


Ellsworth Ratteray also said his ancestor sailed the Rose of Sharon to New York in June the same year with a cargo of potatoes, onions and tomatoes.

In September 1855, Ratteray put the boat up for sale. He gave a detailed description of the boat in a newspaper advertisement: it was made of white oak and cedar, sheathed with yellow metal and every bolt in the keel “goes through and through.”

Unable to find a buyer in Bermuda, he sailed the Rose of Sharon the following year to St Vincent, where it was purchased for $3,000—a significant sum of money. He arrived back in Bermuda in January 1857.

Ratteray, who was also a dairy farmer and an undertaker, amassed an impressive amount of property during his lifetime. Sandys Parish records listed his holdings in May 1859 for tax purposes: three houses and more than 26 acres of land. As a property owner he had the right to vote: in 1858, he was one of 32 registered voters in Sandys.


A family man, Ratteray married his first wife, Rebecca at the age of 26. They had seven children, three of whom, Edward (George), Alexander and Joseph, survived their parents.
Rebecca died in February 1857. He married widow Jane Steer in May the same year. They had four children: Mary Hamilton Seymour Ratteray and Thomas, Jeremiah and Frederick Ratteray.

Ratteray was said to have turned to religion after he nearly losing his life during a violent storm when sailing one of his ships in the Caribbean.

He helped to secure the property on which Wesley Methodist Church in Sandys was built. He was one of several black Bermudian men who invited Nova Scotia-based BME Bishop Willis Nazrey to Bermuda in 1870.

The BME took root in Bermuda and in time would merge with the AME. Ratteray’s daughter Mary later donated land he bequeathed her for the construction of Allen Temple AME Church in Somerset.

Ratteray died on August 24, 1872 at his Somerset residence. An obituary in The Royal Gazette said that he came to Bermuda at an early age, became a ship’s carpenter and “soon perfected himself in the art.” He was also described as “an energetic, enterprising man and a Christian”.

He was survived by his wife, seven children and 15 grandchildren. All seven children and the children of his deceased son, Charles, inherited property. Jane Ratteray inherited a life interest in their home, which stood on 15 acres of property.

Ratteray’s legacy survives through his many descendants who have made a substantial contribution to business and public life in Bermuda.

They include Sir George Ratteray, the first black president of the Upper House (now the Senate); Dr. Stanley Ratteray, a dentist and leader of the Progressive Group, which desegregated cinemas in 1959, Rosalind (Ratteray) Williams, a Progressive Group member, Anglican Bishop Ewen Ratteray, former MP and golf pro Kim Swan, St. George’s Corporation Common Councillor and businessman Gladstone Trott, architect and former MP Walter Brangman and former Living Memories talk show host Oda Mallory.

Stories about Ratteray’s early life and how he came to Bermuda have been passed down his family through the generations, but cannot be verified. One story says he was the son of a slave woman and a Scottish nobleman named Ratteray who was acting governor of the Bahamas at the time of his birth.

No Ratteray is included in a list of Bahamas governors, acting or actual, that is available on line, but Charles Ratteray was described as mulatto in written records. Whatever the truth of his origins, he grew up to become a person of significance.

Writing in Heritage, Dr. Kenneth Robinson said that black artisans, mariners and labourers were “the ‘forgotten men’ in accounts of the Bermuda story”. But enough information has survived to show that “during the first quarter century after Abolition, there were those who participated significantly in their nation’s economy…”

Charles Roach Ratteray was among the most prominent of them.

Howard Lee

(15 August 1935 – 23 August 2012)

During a distinguished career Lee set the benchmark for black sailors to strive for after representing Bermuda in the Finn dinghy at the 1976 Montreal Games.

“Representing your country is one of the greatest things a man can ever get involved in because first of all you have to fight to get there,” Lee told The Royal Gazette during an interview in 2006. “When I got to the Olympics and walked into that big arena it was a hell of an experience for me.

“Travelling overseas to compete in the Finn class enabled me to broaden my horizons and experience many wonderful things.”

At age 13 Lee started sailing competitively in Comets out of West End Sailboat Club as crew for Gates Smith and Sparky Lightbourne before he eventually owned his own dinghy.

In 1956 and 1957 Lee won the Long Distance Comet Race in his boat, High Yella, to become only the fourth skipper to win back-to-back titles behind his idol Ellsworth Lovell.

He also sailed in the Sunfish and Laser classes.

Outside of sailing Lee had a passion for both football and music.

He was a member of the Devonshire Lions team that lost 3-1 to Dock Hill Rangers in the 1959 FA Cup final and as a singer/musician entertained tourists at White Horse Tavern and Swizzle Inn the East End.

The late sailor is the grandfather of Laser and Fitted Dinghy sailor Rockal Evans.

Lee’s success inspired other black sailors such as Glenn Astwood to take to the sport.

“Howard was a huge inspiration for me because I used to watch him from a kid,” Astwood recalled. “I used to always go down and follow High Yella in the Long Distance Race before I even started sailing.

“My father used to take us down to follow the race every year and it was always High Yella, High Yella.”

Astwood later went on to represent Bermuda at the 1988 Olympic Games in Seoul, Korea in the Tornado catamaran.

“I am so sorry to hear that Howard has passed because we always used to chat whenever I saw him whether it be at the yacht club or in the street,” he added. “Howard was a very good sailor.”

Alan Burland, who also represented Bermuda at the Olympics in the Tornado, described Lee as a good sailor and wonderful ambassador for Bermuda.

“I had an awful amount of respect for Howard Lee who was a tremendous man,” he said. “He was a hard worker in an era when things were not easy for blacks in the sailing world.

“He had a wonderful, outgoing spirit and was always so friendly and kind and a hugely competent sailor. His grandson Rockal is obviously a chip off the old block and is a great sailor.

“Howard was a wonderful good sailor and ambassador for Bermuda and supporter of the Bermuda Sloop Foundation. He wanted to help the youth and Bermuda be the best it could be.

Colin Egbert Clarke

(25 January 1935 – 13 December 2014)

Colin Clarke, the first black member to be accepted at the Spanish Point Boat Club, played an integral role in Bermuda hosting the 1992 Comet Class Internationals and the introduction of the Tornado Class to the Island in the 1980s. The Tornado catamaran is a forerunner to the AC45 and AC62 catamarans now sailed in the America’s Cup.

He built his first wooden comet boat in the backyard of his Glebe Road residence and named it ‘Carline’ after his daughter.

Clarke was a past winner of the annual Long Distance Comet Race and Comet Class Yacht Racing Association president for Bermuda’s region.

He also coached Optimist sailing at the grassroots level and had a big influence on East End Mini Yacht Club stablemate Stevie Dickinson, the most decorated sailor in the history of local Comet sailing.

He was a marvellous ambassador for Bermuda’s entire sailing fraternity and promoted sailing tirelessly and was always willing to help at all levels.

His vision included a strong plan to see fully inclusive sailing involving people of all races and walks of life, gender and ages.

He was a trailblazer promoting sailing here and overseas.



Rudy Bailey

  • 10 x Winner of International Comet Class
  • Multi winner of The Edward Cross Long Distance Race
  • Multiple winner of Flag Pole – Flag Pole
  • Multiple Club Champion at West End Sailboat Club
  • Has also represented Bermuda in Optimist Class with Stevie Dickinson

Stevie Dickinson

  • 4 x Comet International Champion
  • 14 x Winner of The Edward Cross Long Distance Race
  • Multiple Club / Comet Class Champion
  • 1st Bermudian to win an Optimist Race in Switzerland in 1972/3
  • also present Rudy Bailey, Kenny Wilson Current over 60 Laser Champion in Carribean region
  • Former Bermuda National Team Football player (6 years)
  • Class Champion 2020 for Comet Class