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Friendships~partnerships~family ties
The Portuguese Connection

Just  four months after the end of The Great War, and at the height of the popularity of the Ford Model T, the operation of the Trinidad Ford dealership commenced in the name of a young Irishman.  On 19th March 1919, the Charles McEnearney Ford dealership was opened at No. 25 Richmond Street in Port of Spain, Trinidad.  What is not widely known is that Charles McEnearney’s partner in business and the co-founder of the well-known automobile business was Robert (Bobby) de Sousa, a member of a long-established Portuguese family.  He was an estate proprietor who had started his working life in San Fernando as a merchant.  Several years after co-founding the company that bore his name,  Charles McEnearney decided to leave Trinidad and return to the United States.  He sold his interest in the business to Robert de Sousa who then ran the entity  at No. 25 Richmond Street as sole owner.


During that time,  the Sheppard family lived at No. 30 Richmond Street, directly opposite to the McEnearney dealership and showroom at No. 25 Richmond Street.  My grandfather, Charlie Sheppard, had bought the large residence where he lived with his wife Elsie Gomez and 12 children until his untimely death in 1931.  It was at the McEnearney business across the street that Robert de Sousa's son Leslie met and fell in love with my father’s sister, Ida Sheppard. A romance ensued and they were married on 22nd July 1933 at St. Ann's Church of Scotland, Port of Spain.  Ida’s parents (my grandparents)  were also of Portuguese roots. The family ties between de Sousa and Sheppard families became even stronger when Robert de Sousa’s daughter  Joyce married my father's brother Charles Albert (Bertie) Sheppard, in 1938.

Charles McEnearney was born on 29 April, 1887 in Rathfriland, Ireland and grew up in County Down.  He was a Naturalized American citizen, having immigrated to the USA as a minor with his parents.  Records show that he traveled back and forth from his home in New York to Trinidad. He brought to Trinidad two American dealerships: the Singer Sewing Machine Company and the Ford Motorcar Company.   He also represented an American company seeking to purchase copra and other coconut-based products.

His USA World War I Draft Registration states that he was then 30 years old, working as the Manager of the Singer Sewing Machine Company in Trinidad in 1917. It appears that he was never called to serve in active duty.   

Charles McEnearney’s good friend was Barbadian Charles MacKenzie, who had the Singer Sewing Machine agency in Barbados. It was through selling Singer Sewing Machines that they met at the start of their lifelong friendship and business relationship. In 1918, they decided to go into business together starting with the Firestone Tyre agency, founding the Barbados partnership Charles McEnearney. In 1922 they obtained the Ford agency for Barbados, selling the popular Model T.  As Charles MacKenzie's son Doug quipped "It seems that they both decided that sewing machines were not for them and cars were much more fun!"

It wasn't until ten years later that  the partnership was incorporated into Charles McEnearney & Co. Ltd., of which Charles MacKenzie became the Managing Director. At that time, the business was owned 50/50 by the McEnearney and MacKenzie families.  Charles MacKenzie's son John David Straghan MacKenzie joined his father in the family business when he was a teenager,  and his younger brother Douglas joined the firm upon completion of his university studies in Canada.  Their three siblings Ron, Neil and Bonnie were shareholders but never took an active role in the company.  Charles McEnearney & Co. Ltd.  was a separate company and remained so until McEnearney Alstons (Barbados) Ltd. owned by the Trinidad company purchased 48% of Charles McEnearney & Co. Ltd. Barbados.  David became Chairman of McEnearney Alstons (Barbados) Ltd., a position he held until his retirement.  The conglomerate continued to grow and eventually became owned by the Trinidad ANSA McAL group.  The Mackenzie and McEnearney families sold their shareholdings and have moved on to other interests


Charles MacKenzie was my father-in-law, though I never had the pleasure of knowing him. I understand that he was a larger-than-life man with a booming voice and a great sense of humour.  He and his wife Winston had had passed away before I was married  to David between 1985 to 2009.  David always spoke fondly about the great friendship between "Mr. Mac", as he was known, and his father who was also known locally as "Mr. Mac."  The two partners, he said “got on like a house on fire” and went on many business trips together.


l/r Charles MacKenzie, Charles McEnearney and his wife Esther McEnearney

When Robert de Sousa  decided to move to Grenada, he sold  Charles McEnearney & Co. Ltd. to brothers George and Melville de Nobriga who, like himself, were Trinidadians of Portuguese parentage. George was born in 1886 and Melville was born in 1893.

Melville prevailed upon Charles McEnearney to return to Trinidad, as he had a good relationship with the Ford officials. This Charles did, buying back shares in the company and becoming an Executive Director, while  Melville de Nobriga was Managing Director of the company.  Melville's younger brother George de Nobriga,  was an investor, but never took an active role in the business.


Melville de Nobriga married Amy Gibson, whose brothers Ralph and Robert "Bunny" Gibson also joined the firm.  In 1925 Robert was transferred to San Fernando where he ran the branch there, while his younger brother Ralph worked his way up from the bottom at the Richmond Street headquarters in Port of Spain, having started working the petrol pumps as a schoolboy during vacation time.   Ralph's brother "Bunny" Gibson died in a tragic accident in 1961, and  in that same year within a short space of time,  his brother-in-law Melville de Nobriga also passed away.   In 1962, following those unfortunate deaths,  Ralph became McEnearney's Chairman and Managing Director.   Ralph held those positions until his retirement in 1982.  Here again we see family ties, as Ralph Gibson  married Charles McEnearney's daughter.


It's interesting to note that Ralph's grandfather had come to Trinidad from England and worked with the prison service attached to the St. James Barracks where my English great-grandfather also served, first with his Regiment and later with the Trinidad Police Force. Charles McEnearney himself was an Irish-born immigrant. The de Nobriga brothers and Robert de Sousa were of Portuguese ancestry.  In Barbados, Charles MacKenzie was of Scottish ancestry, all of his children bearing the family middle name Straghan.

The co-founder of McEnearney & Co. Ltd, Robert de Sousa, better known as Bobby, was a most interesting man.  Born on July 4 1880 in Trinidad, he was educated at Boys’ Model School (later Tranquility School).  He and his wife, Alice Ferreira, had six children (as mentioned above, two of whom married Sheppard siblings). They were Grace, Kathleen, Leslie, Richard (Neville), Lena (Joyce) and Stanley.  They lived in a beautiful home situated near the Savannah in Port of Spain.  Robert was a Freemason, having joined the Prince of Wales Lodge in Alexandra Street, Port of Spain in 1918.  After selling his interest in McEnearneys to the de Nobrigas, he joined Geo. F. Huggins & Co. Ltd., becoming one of the Directors of that company.  In Grenada, he became Managing Director of George F. Huggins & Co. Ltd., the largest trade and commercial concern in Grenada at the time.  Bobby de Sousa purchased and managed a large group of estates in Grenada and is said to have owned a small island in the Grenadines.  He had a keen interest in horseracing and owned many famous racehorses.  He also  became one of the founders and directors of the cinema business in Grenada. 

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The family relates that his wife Alice did not want to uproot her family to move to Grenada, so she continued to live in their family home in Port of Spain so that the children could continue their schooling there.  The couple never divorced and Robert enjoyed the rest of his life in Grenada.  Robert's daughter Joyce and her husband  Bertie Sheppard also moved from Trinidad to Grenada.  Following in his father-in-law's footsteps, Bertie became the Managing Director of Huggins & Co. Ltd. there.


Painting of "Bagshot" - the de Sousa Family home where Alice de Sousa lived with the children in Trinidad

(Courtesy Joan (de Sousa) Bodu)

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l/r:  Bertie Sheppard, Kathleen de Sousa and her father Robert de Sousa, in his garden over looking the harbour, Grenada


Robert with his son Stanley, in Grenada

Robert de Sousa died in Grenada on 21 July 1966 when he was 86 years old and was laid to rest there.  Alice predeceased him in 1962  and her gravesite is in Mucurapo Cemetery in Trinidad.  Their descendants are now spread far and wide - from the Caribbean to as far as Peru, England, Canada and America.  

This story was compiled by me on 17 October, 2021, as I find intertwining of families to be fascinating.

With thanks to:-

  • Ryan de Sousa and family for providing family photos

  • My cousins Joan (de Sousa) Bodu, Kathleen (Sheppard) Henry, and Bernie Henry for sharing oral family history

  • J. David S. MacKenzie who gave me the book "The History of the ANSA McAL Group of Companies – 125 Years of Business" published in 2006.  (David was a contributor of information and photos for the publication.)

  • Douglas S. MacKenzie for providing information

  • Genealogy sites on the internet for research

  • My father Andrew Sheppard for his handwritten memoirs about the Portuguese in Trinidad.


1992, Trinidad - David MacKenzie looks on while

Dr. Anthony Sabga (1923 Syria -2017 Trinidad) of ANSA McAL

presents me with the gift of

"The Book of Trinidad". 

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