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Winston Dookeran

Walking in the Rain –
Without Getting Wet

By Shereen Ann Ali.
Lead feature profile published in TTARP magazine, Issue 3, 2021.
Online link:

Life doesn’t always go according to plan. It can blindside you when you least expect it – as Winston Dookeran discovered when he tried to apply for his first job in Trinidad more than 50 years ago. The Ministry of Education rejected his application, saying his economics degree would be useless to pursue a teaching career within their system.

“I was despondent”, admitted Dookeran, but he refused to give up on either economics as a career or on his quest for a sustainable job. With a steadfast resilience born of his family upbringing in Rio Claro, he explored his options and reached out to the Benedictine monk, Dom Basil Matthews, who at that time was the Principal of St Benedict’s College in La Romaine.

Dom Basil Matthews (1911-1999) was the first Black Benedictine monk in the island, and a man who took to heart the sufferings and challenges of the poor. He established in 1956 his own unique kind of comprehensive school, St Benedict’s College, to try to make a real difference in young lives.

Dookeran, being a South boy, was well aware of Matthews’ good work and respected his educational mission. During Dookeran’s meeting with “The Dom”, Father Matthews must have seen potential in the young man, because he decided to help him: “Come and teach my class in A Level Economics from Monday morning,” he offered.

This first teaching job would mark the beginning of a fruitful career for Winston Dookeran in public service, economics, politics, and academia. Dookeran would go on to become a respected economics lecturer (and later, Professor of Practice) at The University of the West Indies; Governor of the Central Bank of Trinidad and Tobago; and Senior Economist at the United Nations Economic Commission for Latin America and the Caribbean.


In politics, Dookeran would become a Member of Parliament for Chaguanas (twice – in 1981 under the ULF and in 1986 under the NAR); an MP for St Augustine (in 2002 under the UNC); and an MP for Tunapuna (in 2010 as part of the PP). He would serve at senior levels in several administrations: as Minister of Planning under the NAR (1987-91); and later, under the People’s Partnership coalition, as Minister of Finance (2010-2012) and as Minister of Foreign Affairs (2012-2015).

In the late 1960s, a new job opportunity opened up for Dookeran in the Economic Planning Division of the Prime Minister’s Office which launched the rest of his career. William Demas, economic advisor to Prime Minister Dr Eric Williams, and Frank Rampersad, a leading economist, interviewed Dookeran and employed him.

Says Dookeran: “It was a great experience to work with men of that calibre.” He helped do work for Dr Williams’ Third Five-Year Development Plan of 1969. Dookeran often had a ringside seat to observe the working out of issues and decisions at senior levels. This early exposure to leadership processes and economic decision-making would serve him well later in his career.

All of this, however, was a far cry from Winston Dookeran’s early upbringing in the small but diverse village of Rio Claro, a place originally named after a stream (“Clear River”) and known for its farming and forest hunting. People of many different ethnicities lived there, even if few of them had much money to spend. Dookeran remembers how his mother was their lifeline back then:

“My mother was a devout Hindu. She did not know how to write or read in English. She had a major responsibility to bring up seven children after the loss of my father when I was three years old. And she had no regular source of income in those days. In retrospect, I believe she taught us to keep a steady head in adversity, and to always have a steady hand in whatever we were undertaking. Her example was a story of courage and strength and sacrifice.”

Of his father, he says: “I never really knew him. But he went to secondary school and had earned a Cambridge School Leaving Certificate. He greatly valued education. Although he lived a short life, he ensured that all his children went to high school. So for us, education was ingrained as a way out of adversity.”

Dookeran says the most challenging experience of his public life was during the July 1990 attempted coup, when the radicalized Jamaat al Muslimeen invaded the Red House with assault rifles. Dookeran, at the time the Minister of Planning for the NAR,  suddenly found himself as Acting Prime Minister in an emergency situation that could easily explode out of control.

While some people urged him to order an Army strike on the Red House, Dookeran discovered this action could lead to as many as 300 deaths. Dookeran refused to accept this scale of loss and resolved to find another way. The phrase: “Have a steady hand” suddenly came to him – his mother’s maxim, grounded in her level-headed values of moderation, resilience and the preservation of life. Dookeran then opted to accept the help of a US Delta Force team of hostage management experts to resolve the situation more peacefully.

The team flew into Piarco Airport at short notice, set up camp on top of the CLICO building, and gave invaluable insights and assistance, which helped the TT government to negotiate the surrender of the Muslimeen after six tense days.

Since those dramatic events of 31 years ago, Dookeran has long since moved on in his life to embrace other issues. Among his most satisfying achievements, he says, is his founding in 2006 of the Congress of the People (COP), a new political party which advocated for the importance of good governance on its public platforms – a first in local politics, says Dookeran, although he notes that good governance has long been a topic of discussion in academia.

“Within a year, by 2007, we fought our first election. And we were able to get 23.5% of the vote – a great accomplishment for such a young party,” recalls Dookeran. Yet because of Trinidad’s ‘winner take all’ electoral system in which the 41 members of the House of Representatives are all elected by first-past-the-post voting in single-member constituencies, the COP did not get a single seat.

Despite the ups and downs of public life, Dookeran believes politics is an arena with great potential for positive change in society. “Politics is what shapes our future, and it is a noble profession,” Dookeran believes.

His advice to young people interested in politics is to “learn the art of walking in the rain without getting wet.” By this he means learning how to be a principled politician – not always an easy path to tread. In his own words:

“You cannot stand aloof of your people’s sufferings; you have to get involved. So, you must be willing to ‘walk in the rain’ (that is, engage with real issues in your society), but you should also avoid ‘getting wet’ (that is, avoid becoming soaked down or muddied by the negativities). You have to maintain your integrity.”

Dookeran, 78 years old in 2021, thinks the organisation of TTARP is an essential body that reflects care and compassion, is sensitive to the needs of our community as we grow old, and does so with professionalism, pride and dignity. And he has definite ideas about the whole notion of “retirement”, saying:

“Retirement is not a word about life, it’s a word about bureaucracy – the need for institutions to organise their finances and let go of older staff. But life does not retire or go into oblivion just because you reach a certain age. Instead, you can choose to do different things from what you used to do before. And you should do these things in ways that preserve your wellbeing.”

Following his own advice, Dookeran these days is a writer. With several books already published, he is now anticipating the April 2022 release of a new book he has recently authored: ‘The Caribbean on the Edge – Political Systems for Stability, Equality and Diplomacy’ published by University of Toronto Press.

And he is already thinking of his next writing project. 

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