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The leadership question Bermuda cannot afford to avoid

Different strengths: Curtis Dickinson and Jason Hayward

“To be free is not merely to cast off one’s chains, but to live in a way that respects and enhances the freedom of others.”— Nelson Mandela

Bermuda’s leadership contest should be judged not by personality or political loyalty, but by judgment, experience and record. Both Curtis Dickinson and Jason Hayward have served in Cabinet in Progressive Labour Party governments. The more important question is what kind of experience each would bring to the premiership.

Mr Hayward represents continuity with the political style and priorities of the administration of David Burt, while Mr Dickinson offers a more fiscally cautious and institutionally minded approach, shaped by his time working in finance on Wall Street and as Minister of Finance from 2017 to 2021.

Experience under pressure

Mr Dickinson inherited responsibility for a government whose debt burden had become one of Bermuda’s defining economic problems. During his tenure, the Government worked to manage borrowing, reduce debt and restore credibility to the public finances.

He also managed the early stages of the Covid-19 pandemic, when revenues were under severe pressure and demand for public support increased sharply. That required balancing emergency assistance against the longer-term need to protect the public balance sheet.

His record is not beyond criticism. Debt remains high, structural spending pressures persist and Bermuda’s fiscal challenges have not been resolved.

However, much of this was brought about in the last four years under the fiscal leadership of Premier and Finance Minister Burt who claims a “balanced budget” while the potholes have grown larger, cost of living is out of control and Bermudians are facing rents and housing costs out of their reach.

Mr Dickinson has direct experience making the trade-offs those problems require. He has confronted the arithmetic of government rather than discussed it only in general terms.

Mr Hayward’s ministerial experience in labour, community affairs and related portfolios is valuable. He has been a visible advocate for workers, families and communities. But that is not the same as managing government finances through debt, revenue uncertainty and emergency fiscal pressure.

The relevant question is therefore not who has served in Cabinet, but who has demonstrated the clearest readiness to make financially and politically difficult decisions.

Mr Dickinson has the stronger case.

The value of fiscal discipline

A premier must do more than defend the Government’s existing programme. He must decide which commitments can be funded, which must be redesigned and which cannot proceed.

Mr Dickinson’s time at the finance ministry demonstrated the practical meaning of fiscal restraint. Debt reduction and expenditure control may not produce the immediate political rewards of announcing new programmes, but they preserve the Government’s ability to act.

A government that spends without regard to its balance sheet eventually loses choices. More revenue is consumed by debt service, less is available for health, education, housing and infrastructure, and future generations inherit today’s obligations.

That does not mean every decision made under Dickinson was correct. It means policy must be tested against available resources and measurable results.

Mr Hayward’s record reflects important work in labour and community policy, but advocacy is not the same as prioritisation. The premiership requires the ability to connect social policy to economic reality and ensure that programmes and protections are sustainable.

Mr Dickinson cannot claim to have solved every problem. Bermuda still faces substantial debt, high living costs, weak productivity and pressure on public services. But leadership should be judged not only by whether every problem has been resolved. It should also be judged by whether the leader identified problems accurately, explained the trade-offs and took credible steps to address them.

Hayward has shown that he can communicate effectively, defend the Government’s position, and advocate for workers and communities. Those are genuine strengths. But Bermuda’s present challenges require more than political communication. They require disciplined government, financial judgment and the willingness to reject attractive but unaffordable commitments.

The leadership choice

Delegates and PLP MPs have a genuine choice. They can choose continuity with the present administration under a Hayward premiership.

Or they can choose a candidate with direct responsibility for public finances, experience managing spending and borrowing, and a demonstrated willingness to defend difficult decisions.

That is the case for Mr Dickinson. It does not require believing that he solved every problem or that Mr Hayward has achieved nothing. It requires distinguishing between different kinds of ministerial experience and deciding which is most relevant to Bermuda’s present circumstances.

Mr Hayward has shown that he can be an effective minister and political communicator. Mr Dickinson has shown that he can manage difficult financial responsibilities and place fiscal sustainability at the centre of government.

Bermuda must work on its out-of-control billions of dollars debt which, as previously noted, will be handed off to the generations of the future.

We need both advocacy and competence. But with enormous debt, high living costs, weak productivity and pressure on public services, competence under pressure should carry greater weight.

Dickinson has the stronger evidence-based claim to be the candidate of fiscal responsibility, institutional seriousness and necessary change.

The question is not whether he will make everyone comfortable. It is whether he will make Bermuda stronger. The time has come for the PLP to put Bermuda first. Bermuda all the way, All the way Bermuda.

• Renée Webb is a former Progressive Labour Party Cabinet minister and MP. She ran as an independent candidate in the last General Election

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Published October 09, 2026 at 7:59 am (Updated October 09, 2026 at 8:27 am)

The leadership question Bermuda cannot afford to avoid

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