A “Somerset boy” from humble beginnings, Curtis Dickinson credits a life grounded in community for setting him on the path to success in the corporate world and also for the firm principles upon which he stands.

The former Wall Street investment banker, who is running against union stalwart Jason Hayward in the upcoming Progressive Labour Party leadership contest, has been criticised by many for vanishing into the shadows of the back bench since resigning as finance minister in 2022.

While he may have been publicly quiet in Parliament following the rift with David Burt, the Premier, over the Government’s “generous” Gencom deal to redevelop the Fairmont Southampton hotel, his overall impact on the political landscape has been anything but tranquil.

Mr Dickinson’s resignation “on principle” came just days before the national Budget. He then challenged Mr Burt to the PLP leadership and premiership, albeit unsuccessfully, and is now taking the party to court over membership-restricting rule changes he believes are contrary to its constitution.

An interim injunction had the amendments blocked and accordingly, the PLP’s 61st Annual General Conference — where the next leader is to be selected — is on hold until the case concludes.

For a man who has revealed that his first instinct on entering politics in 2018 was to “remain behind the scenes”, Mr Dickinson has instead set the cat among the pigeons, with the traditionally closed internal workings of the PLP now excruciatingly public.

Mr Dickinson, 61, is seen by many as a change agent, even a disrupter, willing to challenge the status quo within his own party.

As the country grapples with a seemingly endless cost-of-living crisis, it is his extensive financial experience that is piquing interest.

A veteran global reinsurance executive, who worked with the Government extensively while Mr Dickinson was in control of the public purse, praised his “incredible” work on refinancing the island’s debt, saying it was one of the most important things the minister achieved in the role.

The executive, who wished to remain anonymous, said: “I never worked with a person like Curtis. He always had the best interests of the island at heart.

“Even those who are not as supportive of him will recognise the incredible financing deals he put together for our debt. It was very strategic and required a great deal of technical expertise.

“I didn’t agree with every decision, I advocate for insurers, but he would always contemplate what was best for the island.

“Bermuda needs solid decision making, governance and less politics. People are ready for a little less drama — fill the potholes, educate the kids, collect tax and help those who need help.”

Mr Dickinson’s five campaign pillars begin with affordable housing, followed by education — calling for a modern and well resourced system like he was afforded at West End Primary School and The Berkeley Institute — accessible and affordable healthcare, public safety and infrastructure.

Two former premiers touched on the attributes of both leadership contestants.

Michael Dunkley, who was premier under the One Bermuda Alliance from 2014 to 2017, described Mr Dickinson as “calm and cool”.

“He has significant private sector experience and strong public and private sector confidence in his financial background and performance. He is not a party insider or hardcore PLP.”

Alex Scott, a PLP premier from 2003 to 2006, said Mr Dickinson brought “an extraordinary background, especially in finance, and that can only help any organisation”.

“Now we have a candidate with Curtis, steeped in banking experience, prepared to bring that experience to the leadership of the PLP.”

The reinsurance source said Mr Burt would be “a hard act to follow” with his grasp of financial policy and politics, adding that “he is ready, at any moment, to step on to the global stage”.

However Mr Burt, who many believe will retain some degree of political control under a Jason Hayward administration, and Mr Dickinson, who on his resignation was praised by Mr Burt as “a steady and thoughtful hand at the helm of the Government’s financial and fiscal strategy”, have been known to differ in direction.

While he is keen on a “rigorous approach to national debt,” Mr Dickinson expressed reluctance over the adoption of the corporate income tax in an interview with The Financial Times in 2021.

The publication reported that he believed “taxing corporate profits would make Bermuda more bureaucratic and add complexity for business … threatening its role as a global hub for reinsurance”.

Bermuda’s total revenue is projected at $2.03 billion in this fiscal year, the first time government revenue has exceeded $2 billion, driven largely by an estimated $753 million in CIT receipts.

The veteran reinsurance executive added: “I wouldn’t say he [Mr Dickinson] was against government working with industry, but he does want to ensure companies are going to do it in a way that benefits Bermuda and doesn’t risk double taxation.”

He added that Mr Dickinson is decisive and quick to action, which he emphasised was crucial in the modern, fast-moving financial sector.

“Bermuda industry is known globally, as is the BMA, for its speed to market. Think about 25 years ago, after September 11, we quickly got to writing new business. That mentality has always served Bermuda well and that is what is lacking in the Bermuda Government.

“Curtis will create a sense of urgency. We are competing globally and the market has never been so competitive so we have to have that mindset.”

A prominent Bermudian politician echoed the point, saying: “People are moving faster than politics. The politics of the country is so far behind. We are advanced in so many ways and change is instantaneous when it comes to technology and business.”

However the politician still had doubts, saying Mr Dickinson will struggle to form a Cabinet from “slim pickings”, and adding: “Curtis has the appearance of being able to move Bermuda into the future; the question is whether it is superficial. Just because you wear a suit and tie, it doesn’t mean you can lead the country.”

A party insider said that there was a feeling among some in the party that Mr Dickinson was too conservative in his ideology and that while he has a solid financial background, he might not be ready to lead.

Mr Dickinson was keen to show there is more to him than the image of a polished, corporate figure with predominantly business interests at heart.

The graduate of the historically Black Morehouse College in Atlanta, where the Reverend Martin Luther King Jr earned his undergraduate degree, and Columbia University, says that while he made his name in boardrooms, he started from humble beginnings within a strong community.

He was raised in his grandmother’s small wooden cottage on Cooks Hill Road in Somerset, surrounded by a large extended family and community that invested in him. Many are credited for contributing to his success.

His young mother, Sheila Dickinson, who was his greatest inspiration, worked “relentlessly”, despite suffering serious health issues, to ensure he and his sister achieved a good education.

While his mother was “the visible force of tenacity”, he had great respect for his father Everard “Buck” Simmons Sr — the “quiet strength” who never used words lightly.

A family who took him in when his mother fell ill, and teachers from West End Primary School and The Berkeley Institute, where the belief that effort mattered was reinforced, all helped to shape him.

Others include professional mentor Tom Mann, a White man who “complicated any simplistic racial narrative” by seeing the potential in a young Black man and investing in him, and Mr Dickinson’s wife Lisa Lee, whom he describes as “the anchor in my life who believed in me when I doubted myself”.

The couple endured tragedy when their first pregnancy ended in loss after just 25 weeks.

“It was traumatic,” Mr Dickinson recalled. But they went on to raise a family together.

Shortly after his grandmother passed away in 2006, his mother suffered a heart attack. That was when “morality entered the equation”, and the same year the family chose to return to Bermuda. His mother passed away in 2013.

“I am the product of the grass roots,” he said. “I believe the definition of grass roots must account for generational progress. Parents and grandparents fought for education, access, civil rights and economic opportunity precisely because they wanted their children to move into spaces from which earlier generations had been excluded.”

One party insider said that Mr Dickinson lives in “upper-class comfort” adding: “He can’t be bought and he doesn’t owe anyone a position.”

While he does not claim any traditional career inside the labour movement, he does say that his family “has always been labour”, as has his wife’s.

“Neither side permits us to forget where we came from,” he insisted.

On the last Labour Day, he issued a statement saying: “Labour is at the foundation of our country’s success.”

Bermuda’s labour leadership still needs convincing. Chris Furbert, the president of the Bermuda Industrial Union, said Mr Dickinson’s resignation from Cabinet “does not bode well because when you are a member of Cabinet there is collective responsibility”.

He also criticised the 2022 leadership challenge, adding: “We haven’t heard anything from MP Dickinson as a backbencher as it relates to labour.

“MP Dickinson has had plenty of opportunities to present himself as a change agent for the workers and the people of Bermuda.”

He said Mr Dickinson paid a “token campaign visit” to the BIU executive board three months ago to gather feedback on what it wants done.

Mr Dickinson said that as his professional career progressed, he felt an obligation to “pay forward”.

His wife feared politics would change him and made him vow never to compromise on his principles for political gain, to which he agreed.

He reflected on how his past met policy. “My concern with housing, healthcare, education, financial stability and community safety can be understood against a childhood in which stability depended heavily on family, work, education and community.”

A party insider said: “The first impression of Curtis Dickinson seems to be, for many, austere or aloof, but that is not who he is. He is a measured sort of person, even shy, but once you approach him he will take you on with a topic. He will come across and engage.

“In caucus, he will make his views known but keeps his cards close to chest in the public arena.

“Like him or not, he comes across in comparison with Jason as more accomplished and mature — accomplished on an international scale for sure — and he is becoming more comfortable with the man-on-the-street profile and role. That too will come.”

McKeisha Smith, who worked with Mr Dickinson at Butterfield Bank as his HR business partner some 20 years ago, said he always put people first.

Ms Smith added: “Whether he was making a difficult decision or navigating change, he never lost sight of the human impact. He genuinely cared about doing what was right.

“He is a man of integrity, a leader of substance and someone who genuinely cares about people.

“The qualities that made him an exceptional leader then are the very same qualities that make him worthy of leading today.”