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Friendships~Partnerships~Family Ties
Unravelling the Connections - Part I

In October 2022 Ford celebrated 100 years in Barbados.  I was pleased to have provided some historical information  to  ANSA's Marketing Manager in Barbados for commemorative promotions

Chapter 1



Charles McEnearney and Robert de Sousa


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 in Trinidad.  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.


Newspaper advertisement - 1926



Leslie de Sousa and Ida Sheppard

Joyce de Sousa and Bertie Sheppard


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, Charles (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. 

Thus, two de Sousa siblings wed two Sheppard siblings.

Chapter 2



Charles McEnearney and Charles MacKenzie

The Ford Dealership

Charles Edward 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 businessman Charles Straghan MacKenzie. born on 12 February 1897. It was through selling Singer Sewing Machines that they first met, as Charles MacKenzie had the Singer Sewing Machine agency in Barbados. It was to be the start of their lifelong friendship and business relationship.  In 1918, the two young men decided to go into business together starting with the Firestone Tyre agency, founding the Barbados partnership Charles McEnearney. In October 1922 they obtained the Ford agency for Barbados, selling the popular Model T.  As Charles MacKenzie's youngest son Douglas quipped to me "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 in 1932 that  their partnership was incorporated into Charles McEnearney & Co. Ltd., of which Charles MacKenzie became the Managing Director.  Charles MacKenzie's son John David Straghan MacKenzie joined his father in the family business in 1951 when he was 18 years old, right out of his secondary education at The Lodge School. He was known as David, but his contemporaries called him "Beaver", a nickname he acquired as a school boy. David was sent for a one-year training course in Dealership Management Administration at the Ford Motor Company Training School at Dagenham, UK.  Upon his return to Barbados, he rejoined the company in 1953.  At that time, the business was owned 50/50 by the McEnearney and MacKenzie families.  His younger brother Douglas joined the firm in 1966 after completing his university studies in Canada. Their three siblings Dr. Ronald MacKenzie, Neil MacKenzie and Bonnie (Montagu) MacKenzie were shareholders but never took an active role in the company

What started off as a simple partnership between the two friends Charles McEnearney and Charles MacKenzie in Barbados grew into a successful conglomerate and eventually became owned by the Trinidad ANSA McAL group.  The McEnearney and MacKenzie and families sold their shareholdings and have moved on to other interests.


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

Chapter 3



John David Straghan MacKenzie and Valerie Anne Sheppard

x1 6 (1).jpeg

l/r Valerie Sheppard, David MacKenzie and John Bellamy

at a corporate event on board a ship - Barbados, 1985.  David was then Chairman of McEnearney Alstons (Barbados) Ltd.

In 2004 John Bellamy became Chairman of the Board of

ANSA McAL(Barbados) Ltd.


The Barbados Advocate - Monday 2 August, 1985

At an ANSA McAL function in Trinidad, 1992

Dr. Anthony N. Sabga O.R.T.T., Chairman and Founder of the ANSA McAL Group of Companies, presents David MacKenzie's wife Valerie with a gift of "The Book of Trinidad". 

David, then Chairman and CEO of McEnearney Alstons (Barbados) Ltd., looks on.

David MacKenzie took over the reins of the Barbados Ford dealership Charles McEnearney from his father Charles Straghan MacKenzie.  He was responsible for relocating the business from the Chapel Street, Bridgetown site to Wildey, St. Michael in 1968.  In 1980 the holding company McEnearney Alstons (Barbados) Ltd. was established, in which McEnearney Alstons of Trinidad took an equity interest.   David was appointed Chairman and CEO of McEnearney Alstons (Barbados) Ltd. and held that position until he retired at age 65 in April 1998.   He was then invited to remain as Chairman for a further couple of years.


Through an unexpected and tragic turn of events in my life in 1984, I became a part of the MacKenzie family when I married Charles MacKenzie's third son,  David.  I never knew my MacKenzie father-in-law as he and his wife Ella Winston (née Cole) had already passed away in the seventies.   Author Simon Kreindler, childhood friend of Charles MacKenzie's younger son Douglas (Doug), describes Charles in his book "Peddlers All" as "a tall imposing man with a deep, booming voice, he was quite deaf and communicating with him was a challenge. He smoked a pipe and kept a double-barrel 12-gauge shotgun in the corner of his bedroom.  Even as kids we understood it was meant to warn the help that burglary would have serious repercussions."   David always spoke fondly of his father. I gathered that he was a larger-than-life man with a wry sense of humour.  He often recalled that when his father  presided over a board meeting and an important matter was tabled he would declare, "All those in favour say 'aye', all those against say 'aye' resign!".  Although it was said tongue-in-cheek, I believe David admired and emulated his father's management style. He spoke about the great friendship between "Mr. Mac", as Charles McEnearney was known, and his father who was also known in Barbados as "Mr. Mac."  The two partners, he said “got on like a house on fire” and went on many business-cum-pleasure trips together.


David had a meticulous eye for detail - oftentimes to a fault.  He was measured, determined and decisive in both his business affairs and private life.  Not surprisingly then, he proposed marriage to me just a couple of months after we first met. We were introduced at mutual friends' home on 24 February 1985.  Nine months later, we were married at St. Dominic's Catholic Church, with a reception at the Barbados Yacht Club. It was 30 November 1985.  There were fireworks and celebrations all over the island that night as it was Independence Day in Barbados - the 19th year of Independence.  Apart from family members from both sides, many of the guests at our wedding were David's Barbadian business associates and several fellow directors who had flown in from Trinidad, including Conrad O'Brien, Chairman/CEO of the McEnearney Alstons group.  Since David was a director of the daily newspaper, The Barbados Advocate published a photo of us on their front page with the headlines "MacKenzie Weds Again".

It was a second marriage for both of us.  His first wife Dr. Anne Bayley had died in December 1984 after a short illness of cancer, and my husband J.A.K (Tony) Archer, a well-known Barbadian equestrian sportsman and businessman, had died suddenly of cardiac arrest during an asthma attack in July of that same year.  I was a 37 year old widow with a family of five children ages 7 - 18 and David was a 52 year old widower with two adult children studying abroad at university.  We were brave and optimistic, both of us, to undertake this merger of families with very different family roots and backgrounds.   In many ways, it was an unforgettable period of my life and the lives of our families and extended families on both sides.  David and I separated in 2008 and divorced in 2009.

The intention of this chapter, however, is not to write about the private life we shared during a span of 22 years, nor about the character of my former husband.  Nevertheless, it was within those years that the Ford business David had taken over from his father expanded, becoming one the most well-known and successful conglomerates in Barbados.  It was during this period that he reached the peak of his business career.  As the Chairman's wife, I  was by his side at all the countless corporate events and social occasions associated with such a position.  He was unaware that I kept newspaper clippings of some of the more important ones - special milestones that may otherwise have been forgotten.  In 2001, our friend  Conrad O'Brien called me to say he wanted to nominate David for a national honour in acknowledgement of his contribution to business.  David and I prepared a detailed CV which was submitted to the relevant authorities under Prime Minister Owen Arthur's government and I kept a copy of it among my memorabilia.  For reasons unknown to me, that honour was not granted.

"Friendships~Partnerships~Family Ties" -  I muse on the twists and turns of life.   In 1933 my father's sister Ida married Robert de Sousa, son of the owner and co-founder of Charles McEnearney in Trinidad.  In 1985 I married David MacKenzie, son of the co-founder of Charles McEnearney in Barbados.  Had I known my family history back then, it would have been fun to talk with Aunt Ida about how she met her husband Leslie de Sousa at the Ford dealership across their street in Trinidad.  During a visit with David a few years ago, I told him about what I'd discovered.  It was then that he handed me the book "The History of the ANSA McAL Group of Companies – 125 Years of Business in the Caribbean". I should have also reminded him that my Trinidadian Aunt Ida came to our wedding.  It was she who played a piano duet with her sister Jessie (Sheppard) Brash at the family party held the night before that  blew him away.  He said he'd never before seen the likes of it. 

On my last trip to Barbados in April 2023, I visited David at his home, the same home we shared from 1985 to 2008.  It was soon after his 90th birthday.  When we said our goodbyes at the familiar front door, we both knew it would be the very last time.  I had paid my respects and left feeling that he was already at peace.  David passed away on 17th September, 2023 and was interred at his family plot at Westbury Cemetery, Barbados, after a private funeral service on 24 October, 2023.

October 1995 at a gala to celebrate the 100th Anniversary of the founding of

The Barbados Advocate
Company officials and wives at the gala:  
l/r Mrs Minerva Sabga, Group Chairman Anthony Sabga, David MacKenzie and his wife Valerie, Monica and Douglas Maloney,  Colin Murray

The Synchronicity of Life . . . I find that tracing the intertwining of families and events is fascinating.


This story was first compiled by me on 17 October, 2021. 

On 4 November, following the death of my former husband David MacKenzie on 17 September 2023,  I added Chapter 3.  All of the newspaper articles are from my own collection. 

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" by historian Gerard A.Besson, 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.

""People are trapped in history and history is trapped in them" -   James Baldwin

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