Caymanian Roots

Before stepping into the political fray, Winston Connolly had an enviable life. He was a successful lawyer, a partner in a fiduciary services firm with a wife and young son. Along with the comforts of financial security, Winston also had an active social life. But as a proud and patriotic Caymanian, he was not able to sit back and simply watch the chaos unfold in the wake of the arrest of the then premier McKeeva Bush. He knew he had to do something for his people and his country.


In May 2013 he was elected as an independent Member of the Legislative Assembly and for the next four years worked tirelessly, in the face of huge adversity, to push for change and build a better future for Cayman.

“I wasn’t a politician,” he insists. “I was just someone who felt compelled to help my country and my people, given the circumstances that we found ourselves in at the time.” However, his ideals and his dedication cost him dearly.

Choosing to give up his partnership in the fiduciary services firm, and forfeit the financial security that went with it, was the single hardest decision he has ever had to make. But doing nothing was not something he would have been able to live with.

“The country that gave me so much was under threat,” he says. “Life, as I knew it, was at stake…. In many ways it was not a choice – even though in the back of my mind I knew there would be a huge personal cost.”

Without his partnership income, his wife Lesley became the primary breadwinner. With Winston on a significantly reduced salary, they found themselves paring back their lifestyle and liquidating assets to live within their means. But financial sacrifices were only the beginning. As a politician and public figure, the intrusions into their private life were constant.

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“We had previously done a lot socially, but going out became a burden,” he says. “There are zero degrees of separation in politics.”

Everybody wanted a piece of him. After a while, he stopped going to the grocery store or even out to restaurants to avoid attention. Eventually, the intrusions became so hard to bear that he and Lesley took the decision to rarely venture out at all, unless they had to. They even stopped their date nights, which they had done since they were married in 2008, because people would often inject themselves into the date to try to discuss politics.

Meanwhile, in the political arena, Winston fought hard for what he believed in and spoke his mind, regardless of the opposition he encountered. During his four years as an MLA he remained an independent, speaking out on issues that others dared not address.

“I’ve been called all sorts of names. I lost acquaintances, I was ridiculed and castigated, and have probably been blackballed from my chosen profession as a lawyer,” he admits. “I’ve made lifelong political and professional enemies for my stance on equality of opportunity for Caymanian lawyers.

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However, one of his proudest moments was when he brought the Private Member’s Motion that eventually resulted in the unanimous vote for the previously shelved National Energy Policy for the Cayman Islands. When the other members of the coalition government didn’t see the urgency of getting an energy policy off the ground, Winston decided to host his own international energy forum. Irrespective of initially having no support, he used social media to help turn the tide. Ultimately, he was able to bring a motion that was unanimously approved by the entire Legislative Assembly, with the result being bi-partisan support for the significantly increased use of renewable energy in Cayman. At the time the motion was passed the target for renewable energy was 1% and it has now been set at 70% usage of renewable energy by 2037.

In spite of the immense and sometimes unbearable pressure he was under, the fact that he could make a difference for his country kept him motivated. Unfortunately, both the long working hours and his desire to help his country, had a damaging effect on his relationship with his wife and children. For example, in 2015 Winston and Lesley welcomed their second child Edyn into the world. However, he was so busy, that the only time he saw his children awake was on weekends. “Because my children didn’t see me, they didn’t know me. They clung to their mother or other family members,” he recounted.

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Lesley too was under incredible strain. Not only was she holding down a 60 to 70 hour a week job, but she was also the one handling all the domestic chores, whilst trying to fill the role of both mother and father in her husband’s absence. He notes, “It was not fair on her, the children, or the other family members who had to step in to take my place.” His family life was in jeopardy and the time had come for him to put them first.

Winston has always said – to anyone that would listen – that he does not love politics and only planned to be there for a limited time. For four years he gave it his all, and thus in May 2017 felt able to walk away with this head held high, knowing he had done all he could.

On Family Life

Winston’s deep-seated sense of duty to the country and the people he loves was no doubt shaped by his upbringing. His family was not political at all: He doesn’t recall ever discussing politics with his parents and doesn’t believe that they would have wanted him to become a politician. However, the values they taught him contributed to him feeling a call to public service.

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He was raised in what he describes as a strict but loving home in North Side. His mother a teacher and his father an accountant with the Public Works Department were a humble Christian couple who emphasised the importance of faith first and foremost, followed by family and education.

They always instilled in their children the principles of charity and giving back with his mother encouraging him to become involved in philanthropic clubs. This was a practice he continued into adulthood having served as President of Rotary Sunrise, a board member and vice president of the Cayman Islands Cancer Society, a volunteer on the Legal Befrienders groups and a member of the Joanna Clarke Excellence in Education Award Committee.

When it comes to raising his own children, Winston hopes he can replicate many elements of his own childhood, but in particular the focus on family. He observes that with a strong family unit around you, you can take on almost anything.

Whilst his own upbringing was very regimented, with time allocated to study, piano lessons and reading, Winston and Lesley take a less restrictive approach with Wade and Edyn. They encourage them to make time for sport and social activities, (things that Winston feels he missed out on) and they encourage reading “to expand their minds and comprehension, and to escape to imaginary and far away places.”

Ultimately, they strive to lead by example – treating everybody with love and respect so that their children will do the same. In Winston’s view, there is no such thing as perfect parenting – you just try to be better at it today than you were yesterday.

On Education

Like any parent raising children on a small island, there are aspects that worry him. One is that living in Cayman will mean their exposure to other lifestyles and cultures will be somewhat limited. But the benefits of growing up in a safe, loving and secure environment, and in a place they feel connected to, makes it worthwhile.

His greatest concern, however, relates to the educational opportunities available to children growing up in Cayman. A passionate advocate for education reform, he believes that the public school system here is generally failing young people. The low expectations the system has for its students, he says, in many cases, is turning out low achievers. This is why, during his term in politics, he told the Assembly that he would not send his children to public school, and that he would make no apologies for it until the system was fixed.

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Winston was a gifted student himself: He was the Leo’s Club Child of the Year in 1982 which meant that at the age of eight, he won a university scholarship* [*Editor: At the time the first prize for the Leo Child of the Year contest was a full university scholarship guaranteed by the Cayman Islands Government, although the child was required to maintain high grades up to graduation from high school.] However, he still felt ill-prepared for university when the time arrived. Even back then, the difference in attitudes to education in Cayman as compared to the UK were clear to him. His friends who went to boarding school in England were sitting more GCSEs and more A levels than their counterparts in Cayman.

“At the time I was grateful, but later it was very apparent that I could have been pushed harder, and I always wondered why, as a country, we didn’t. Was it because we believed our students couldn’t?”. Ever since then, this question has fuelled his passion for educational reform. Given that young Caymanians will one day be competing for jobs with their peers from the US and UK, he argues, why are the educational standards here not being raised to at least match those of the competition? If we raise the bar for education, surely the students will rise to the challenge.

If policy makers truly committed themselves to raising standards, he believes Cayman could have an education system that would be the envy of the region. “We could graduate scholars who could take their place among peers anywhere in the world. Why shouldn’t we set a goal to have Cayman’s first Rhodes Scholar? Why not instil in our students the drive, the idea, to go after something like that? Is it because we think they can’t? Or is it because we think too small? These are the questions that keep me up at night and drive my views on education.”

Despite his passion on this and many other matters, Winston Connolly is, for now, changing course. He’s left a career in law, stepped back from politics, and is starting over as Managing Partner at boutique financial services firm Lainston International Management (Cayman) Limited. He and his family have weathered the storm that was a life in the public and political eye, but they didn’t come out unscathed. His priority now is rebuilding his relationship with his wife and children.