Olive Richardson-Trott was an extraordinary Black Bermudian woman born on Christmas Day 1922. Her parents, Campbell and Una Richardson, lived on the corner of Dock Hill and North Shore Road. Beside their home, they ran a small, wooden mom and pop shop where they also made and sold ice cream.

My original plan was to write only about their daughter, but my friend and fellow researcher, Dale Butler, shared with me a most interesting article relating to her father in The Royal Gazette of 1949. I was so captivated that I just could not resist including his story as well.

In 1896, 12-year-old Campbell Richardson worked in the Phoenix Bottling Company on Queen Street, owned by F.W. Grantham. In the winters of 1907 through 1916, he was employed as a bellman at the Hamilton Hotel, followed by a brief stint as a painter at H.M. Dockyard.

In 1922, he was the first person to introduce hot dogs to Bermuda and in that same year purchased his first red and yellow wagon for £20 from Clifford Roberts, of St George’s. He operated this lunch wagon near No1 Shed in Hamilton, where he sold mineral, candy bars, cigars and hot dogs.

He was employed as a warehouse man on Front Street for FJG Foote during the day, tended his store in the early evening, then drove his brightly coloured wagon back to Front Street, where he remained from 10pm until midnight. At that time, there were no restaurants open at night but there were a few movie theatres in Hamilton such as The Victory on Queen Street, Colonial Opera House and the Mechanics Hall that closed at 10.30pm.

Eventually, his son, Donald, managed the business during the day while his father operated the wagon every evening from 7.30pm until past midnight. Before the First World War, the Richardsons sold home-made root beer, ice cream and water ices, but sugar rationing ended that part of the business. Many of his early customers were tourists who asked for frankfurters/hot dogs, which were not available here. He was able to order 25 pounds of them through an agent and sold out immediately. During wartime, he was unable to obtain hot dogs and turned to making hamburgers until no more meat was available. It was at that point he decided to sell bacon strips on a bun.

In 1927, during the development of Tucker’s Town, he purchased a second wagon and hired a man to drive it. This wagon catered to the workmen and later the golf course caddies and carriage drivers. In the 1940s, during the building of the American Base in St George’s, he had progressed to a motorised lunch wagon and catered to the men employed during and after its construction.

The new, much larger Richardson’s Restaurant, known for its beef pies, codfish cakes and home-made ice cream, was a wooden structure with a corrugated zinc roof farther along North Shore Road opposite Grace Methodist Church. In 1973, the wooden structure was demolished and replaced by a two-storey stone building.

Olive, the youngest of their four children, attended The Central School and upon completing her primary education joined her parents in the restaurant business and worshipped at Grace Methodist Church. On New Year’s Eve 1942, she married mason Charles Kenneth “Joe” Trott. They had one son, Kevin, who died in his teens.

Olive noticed that many of the young people in her neighbourhood were in need of direction and wholesome entertainment. In 1948, she formed the Youth Advancement Association. It was located to the rear of the restaurant property, where she had a merry-go-round, a maypole and often held neighbourhood bazaars.

Senior and prominent persons from within the Black community were invited to speak to the youth in an effort to emphasise the importance of education, pride in oneself and pride of country. Among the inspirational guest speakers were Sir Edward “E.T.” Richards and lawyer David Tucker. It is believed that in seeking speakers and entertainment for her youth group, she hit upon the idea of promoting speakers and local entertainment, which eventually expanded to international acts.

Mrs Trott and her close friend and neighbour, Erma Washington, formed one of Bermuda’s first majorette troupes. Although Olive had no dancing skills, Erma did. She was a brilliant dancer.

The majorette outfits were made by a Mrs Stowe and, as they were unable to obtain majorette boots, they had to be creative. They wore white sneakers and created the illusion of boots by wrapping white oil cloth and taping it around their legs.

In writing this article, my husband recalled that Ms Washington had been his Standard 1 teacher at Northlands Primary School, as well as the school’s gym instructor.

Erma Washington was recognised as one of the first majorette leaders on the island and was renowned as a majorette dancer extraordinaire. She gave exhibitions on majorette drills and dance steps at the Colonial Opera House and performed at Castle Harbour Hotel. She later married noted dancer Brian Butterfield, and as a couple they entertained at the Half Moon Hotel in Montego Bay, Jamaica, during our off-season.

The Easter Parade was discontinued during the war years, but when it resumed in the 1950s, Ms Washington and Brian Butterfield led the North Village Majorettes, accompanied by the North Village Band, down Front Street. Before this, Black participation in the Easter Parade was denied, as it had been a racially segregated event.

In the 1950s, Olive Trott spearheaded the careers of entertainers such as Michael “Curtis” Clarke and Steven “Speedy” Ming. She promoted them in hotels and nightclubs such as the Atlantic Beach Club on South Shore, Warwick.

She brought 13-year-old Stevie Wonder, accompanied by his mother, to Bermuda in 1964 and over the years he returned several times, including 1970 when he spent his honeymoon here. Olive Trott provided for his performances local opening acts such as the Aldano Quartet, Gene and Pinky Steede, Elva Simons, The Keynotes and the Dancing Highlights.

Before long, Olive Trott Productions was formed and she became known as the first Black Bermudian female promoter of local and international entertainers. She loved to travel and did so frequently. Her winning and outgoing personality enabled her to make many friends and invaluable contacts. As Wentworth Christopher said recently: “She was never chained to the rock!”

During her travels, she met a couple who were entertainment promoters. This proved extremely fortuitous when Terry Brannon, of the Forty Thieves nightclub, approached her regarding bringing in Black entertainers who would appeal to his local clientele. She was a shrewd businesswoman who realised that if she acquired up-and-coming talent, they would be more affordable. She brought to the island James Brown, Frankie Lymon, Dizzy Gillespie, Billy Eckstine, Sarah Vaughan, Nancy Wilson and numerous others. Many remember sitting on the wooden bleachers at Somerset Cricket Club in 1964 when James Brown performed there.

It was in 1964 that a Jamaican friend, who held the franchise for the Miss Jamaica Beauty Pageant, suggested she apply for the franchise to hold a similar event in Bermuda. Her friend was allowed by the Miss Universe Pageant Committee to subfranchise Mrs Trott to hold a contest in 1965. The first pageant was held in that year, but in 1966 she acquired the sole franchise.

Bermuda was first represented in the 1965 Miss Universe Pageant by the late Elaine Simons. Rehearsals and the actual event took place at the Miami Beach Auditorium. At that same time, the boxer Muhammad Ali occupied a portion of the auditorium complex for training.

Olive Trott observed that Muhammad Ali showed a particular interest in the Bermudian contestant Elaine Simons. She suggested that if he thought she was attractive, he should come to Bermuda and see all the beautiful women here. This invitation was suggested in July 1965 and by that September, he had arrived here to hold boxing exhibitions at the Government Tennis Stadium. He brought along his sparring partner, Kid Gavilan, and stayed at the Leopards Club Plaza.

The referee for these events was Bermuda’s own boxer, Freddie Thomas. He visited the children at The Central School and Prospect School for Girls. He was invited by government dental hygienist Albertha Daniels to visit a special education school where he used a large tooth and brush to promote the importance of dental care. In another event, he selected a young boy from the audience, gave him a few tips on boxing and then challenged him to box against him. The match progressed and when the young boy delivered a blow the world-famous boxer “fell” to the stage. Of course this was all a part of his humour. On his visit in 1974, he stayed at the Hamilton Princess and visited the Robert Crawford School.

Wentworth Christopher, was a police officer during the first visit of Muhammad Ali. He happened to go into Richardson’s Restaurant when he was approached by Mrs Trott to oversee certain details of the boxer’s visit. By 1968, Mr Christopher had left the Bermuda Police Force to assist full time in organising and planning numerous events and activities of the business. In 1972, Mrs Trott handed over the reins of the Miss Bermuda Pageant franchise to Mr Christopher.

Olive Trott’s husband was devoted and supportive of all her endeavours. He supported and assisted in the family restaurant business; he supported her during absences from home until the early hours of the morning overseeing events; and he supported her many travels abroad to secure entertainers.

The partnership with Mr Christopher enabled her to head into semi-retirement. Assuming the leadership of the franchise was a mammoth responsibility, covering aspects of the competition that were little thought about by those of us viewing the pageant festivities. Coaches had to be employed to assist the contestants with diction, deportment, speech, make-up, etiquette and a knowledge of local and world affairs.

The bathing suits worn by contestants were selected from the Catalina brand, described as one of the oldest clothing manufacturers in California at that time — and as a token of gratitude and remembrance of the event, local judges were given engraved silver trays from H.S. and J.E. Crisson Ltd (known today as Crisson Jewellers).

It was not until 1970 that a Bermudian contestant, Margaret Hill, gained international recognition when she was declared the most photogenic contestant in the Miss Universe beauty pageant. Upon her passing in 2024, The Royal Gazette reported that in the contest of 1970 she wore a natural Afro hairstyle, breaking down barriers for Black women in fashion, and was one of the first Black women to take this award.

It also reported that her success led to Bermuda receiving its first invitation to participate in the Miss World competition, held in London in 1971. Unfortunately, Ms Hill was unable to participate because she was tied to a modelling contract, so was replaced by runner-up Rana Furbert.

Another dream of Olive Trott came to fruition in 1979 when Miss Bermuda, Gina Swainson, was crowned the first runner-up in the Miss Universe contest. In that same year, to the delight of the entire island, on November 15, she was crowned Miss World.

This was a true testament to Ms Trott, who had the foresight and perseverance to present Bermudian women on the world stage every year from 1965. She had also been wise in handing over the reins to Mr Christopher, whose vision and skills moved the pageant forward.

In 1972, Olive Anne Trott was awarded the Queen’s Certificate and Badge of Honour, and upon her passing in August 2011, her personal friend and physician, Ewart Brown, is quoted as saying, “Olive Trott was a special lady with a magnetic personality and a contagious smile.”

Olive Richardson-Trott will be remembered always as a fearless, trailblazing businesswoman and community leader.

References:

The Royal Gazette, July 1949

Jazz of the Rock, Part 2, 1978

The Royal Gazette, March 2024

• Cecille Snaith-Simmons is a retired nurse, historian, writer and author of The Bermuda Cookbook. Special thanks to Wentworth Christopher, Dale Butler, Enid Simmons, Bill Anderson and Billy Young, as well as my husband and research partner, Lionel Simmons