In Cayman’s house of cards, who has the winning hand?

It’s the election before the election, a behind-the-scenes race to recruit candidates and form new parties and teams that can seek to lead Cayman in an evolving political landscape.

As many as five different groups could be in the mix for 2025 amid signs that the islands will turn its back on the “experiment” of an independent run government.

From the confusing soup of freelance operators that contested the national vote in the last election, new alliances based on personality and policy are beginning to emerge.

And new players are seeking to fill a perceived gap in terms of structure, leadership and ideology on the political scene.

With the election set for 30 April next year, much remains in flux.

Compass journalists spoke to over a dozen political insiders to compile this story. Many of the conclusions are caveated with the disclaimer that few alliances are, as yet, set in stone.

It is a political house of cards, with multiple groups seeking to put together a winning hand, but the pack could shuffle and reshuffle many times before nomination day.

The state of play

What appears certain is that few will run as bona fide independents.

Perhaps the most ambitious of the new groups is led by political newcomer and former EY partner Dan Scott, who the Compass understands aims to run a slate of around 15 candidates.

The Progressives – the only established party in Cayman currently – are aiming for a similar number.

The already slim chances of the current government coalition, known as the United People’s Movement, running collectively on its record, vanished with the decision of deputy premier André Ebanks and three others to part ways with the group.

Now Ebanks has indicated the breakaway four will run together as a group at the next election and are looking to recruit and work with others in a new political team. Speculation links former Premier Wayne Panton to that group, but he has not commented on his allegiances.

Even the remnants of the UPM – now a seven-person coalition – are expected to splinter in different directions ahead of the election.

However, efforts to put together a team of like-minded candidates from the core of the original PACT coalition are progressing.

Former Deputy Premier Chris Saunders, former Speaker McKeeva Bush and Cabinet ministers Jay Ebanks and Kenneth Bryan are among those understood to have held talks over running collectively. (*Bryan has subsequently denied being involved in any talks with any group at this stage).

Bush launched a non-profit Organization for a Better Cayman Islands last month, setting out broad policy goals and indicating an intent to back candidates for the next election.

North Side MP Jay Ebanks is emerging as a possible parliamentary leader among a number of credible candidates within that group.

The allegiances of the current premier, Juliana O’Connor-Connolly, remain vague. She has insisted she will not stand for re-election, though as with several other parliamentary veterans, such proclamations are generally viewed with scepticism up to nomination.

If she does contest the election, she would likely face a tough race on Cayman Brac East against Scott, who, the Compass understands, intends to run in that constituency.

Current deputy premier Kenneth Bryan has also yet to confirm which group, if any, he will partner with at the next election.

While a handful of incumbents in safe seats could theoretically hedge their bets up to election day and beyond, observers close to the situation believe most will partner up with existing or emerging groups.

One political figure likened the current process to an NFL draft – with emergent groups rivalling each other for the signatures of coveted candidates.

The biggest doubts surround current government members.

Partially, that is because they are bound by the collective responsibility of Cabinet, making it difficult to publicly declare new allegiances outside of that group. The decision of André Ebanks, along with Katherine Ebanks-Wilks, Health Minister Sabrina Turner and parliamentary secretary Heather Bodden to resign from government has given them freedom to campaign.

Other Cabinet ministers may have to wait a little longer before forging new alliances – or at least making them public.

“I don’t think there will be any genuine independents,” said one individual, who ran in 2021. “Progressives and newly forming parties are reaching out to prospective ‘independents’ … so they will be agreeing terms behind the scenes.”

If that comes to fruition, it will mark a sea-change from the last election, where all but nine of the 52 candidates ran on an independent ticket.

New kids on the block

One of the worst kept secrets in Cayman is that former EY partner Scott, who also previously chaired the Education Council, is putting together a new party.

Scott is likely to run in Cayman Brac East – a seat which O’Connor-Connolly won last time in a two-horse race with Elvis McKeever.

Former Olympic cyclist Craig Merren, businessman Gary Rutty, bank executive Carmen McField who has also been on numerous government boards, are inked in as part of Scott’s team.

A handful of other names have been mentioned in connection with that group of around 15 potential candidates, including some in high-profile private-sector jobs who are expected to officially commit closer to the election.

There is some competition with the Progressives to scoop up sitting members of government to run as part of the ticket.

New leadership, new faces for Progressives

The Progressives party faces similar hurdles as it looks to put together a fresh team under the leadership of Joey Hew.

The party, which came into the 2021 election as the senior partner in a coalition with a handful of independent candidates, was left with just six MPs following that poll and the defections of two of its former ministers O’Connor-Connolly and the independent Dwayne Seymour.

The Compass understands both of those could come back to the group, either as party members or as affiliated independents, contingent on discussions taking place over the coming months.

But O’Connor-Connolly’s recent insistence that she will not run, as well as doubts over whether at least four of the current parliamentary group will seek re-election, creates considerable uncertainty around the Progressives ticket.

Former Premier Sir Alden McLaughlin has insisted he is not running, and Roy Tatum, his long-time friend and advisor, is being tipped to stand in Red Bay.

Moses Kirkconnell, who was deputy premier for eight years, is also considered unlikely to run, although the Progressives believe they have a strong successor lined up for that seat.

Similarly, there are doubts over George Town MPs David Wight and Barbara Conolly. Both remain deeply committed party stalwarts and would seek to support and back an alternate Progressives candidate if they do decide to step down.

So far, Craig Frederick, the owner of Swanky International, and Justin Ebanks, who contested the last election as an independent in North Side, have been publicly mentioned as likely candidates.

Hew said the party would be learning its lessons from the last election when it believed it had alliances with independent candidates who ultimately went on to form an alternate government.

“There will be no loose affiliations,” he said. “We plan to run a slate of 12-15 Progressives candidates.”

Hew said the process of putting that team together would be selective.

“I have promised something fresh and we have to deliver on that. We are being very deliberate about the candidates we are approaching,” he added.

At least two current Cabinet ministers are understood to be on the wish list.

A reshuffled PACT?

Former Premier McKeeva Bush, who aims to run candidates under the umbrella of his newly launched Organization for a Better Cayman Islands, has named Chris Saunders, Jay Ebanks and Kenneth Bryan among those he would like to work with.

Bush has not put himself forward and would not likely be considered for the political leadership of that group.

Saunders or planning and infrastructure minister Ebanks, if he agrees to be part of the team, are being considered for that role.

Outside of the sitting MPs, planning lawyer Sammy Jackson, a candidate in Red Bay last time out, and Dr. Sidney Ebanks, a physician at Doctors Hospital, are being pursued as potential candidates.

Bodden Town West MP Saunders told the Compass he believes a group of at least eight candidates can be put together.

He said he was looking to work with people of courage and conviction who could get things done. Highlighting immigration reform as a non-negotiable policy priority for anyone seeking to join the group, Saunders said, “We have kicked the can down the road for too long and we need to be prepared to take a firm line on some of these key issues.”

Saunders maintained a government of independents can work, and insisted he was less concerned about what structure the group takes than ensuring the right composition and leadership was in place.

He indicated that he would not rule out working with anyone the electorate chooses if a coalition becomes necessary.

But, he added that he had “learned his lesson” from the last time and insisted the leader of any group or coalition would have to be chosen carefully and be able to “get the job done”.

The breakaway four

The resignation of André Ebanks and his three fellow MPs spelled the end of the independent coalition as a majority government and effectively created a new political team.

Speaking at a press conference following that decision, Ebanks said the group would run together and were actively seeking candidates who shared their values and policy goals to run with them.

It remains possible that they could merge with one of the other groups or reach out to potential independents to put together a larger slate of candidates across multiple districts.

The political future of Wayne Panton, who initially led the PACT coalition of independents and would likely be considered a strong ideological fit with that group, remains unclear.

While Ebanks has emerged as the spokesperson and political leader of the breakaway four, Panton is another potential figurehead for that group, if he does join.

A sympathetic read on Panton’s short tenure as premier comes from political veteran Roy Bodden, who believes the Newlands MP had many of the right ideas but lacked the political ruthlessness to hold a divided team together.

“I think he has the right ideas,” he said, “and I think he could definitely get public support. He has credibility, he just lacked a little bit of leadership confidence.”

Panton, who ran with a small team in 2021 under the banner of ‘Community builds country’, has yet to comment on his plans.

Disillusionment and ‘pirate politics’

Former Sports Minister Osbourne Bodden, who ran with Panton’s group in the last election, ruled out another shot at office, saying, “My answer is quite simple. The political landscape is a mess, and I want nothing to do with it.”

Bodden’s reticence reflects a more general theme from prospective candidates who spoke of disillusionment and disenfranchisement with the in-fighting and instability of the last three-and-a-half years.

Roy Bodden believes people are generally fed up with what he describes as “pirate politics”.

He added, “I am disappointed that we haven’t developed more political maturity at this point in our evolution as a country. We have been experimenting with this stuff for years.

“I am not a fan of the Progressives, but I have to give them credit for realising the only way to govern is to have an agenda that you can campaign on with a majority of like-minded people.”

Horse-trading and uncertainty still likely

But the likely end of the era of the independents comes with no guarantee that Cayman will get a clear result and avoid the confusion and horse-trading that took place after the ballot last time around.

With between three and five groupings or parties likely to emerge and a sprinkling of independents still in the mix, Cayman could be in for another uncertain result post election.

Unless one of those parties pulls in 10 of the 19 seats, a coalition government will need to be formed, and that will once again mean closed-door discussions after the votes have been counted.

One Progressives insider spoke confidently that the party could sweep the election in a backlash against the uncertainty and political chaos that has prevailed since 2021 of shifting independent coalitions. But others in the party, and in the various alternative alliances, caution some form of post-vote partnership may be required.

This is not uncommon in many countries where coalition forming is ingrained as part of the process when results are unclear. But there is added uncertainty in Cayman, which lacks a clear process for how those discussions take place.

Last time out, it was a week after the election before the government was announced, with various groups prematurely announcing victory before agreement was finally reached to put Panton’s PACT coalition into power.