Gang killer’s affair with prison officer linked to security concerns

Gang killer Osbourne Douglas was involved in a relationship with a former Cayman Islands prison officer that began while he was at Northward Prison and was still ongoing early last year, according to court documents.

The affair is cited by the Governor’s Office as one of the reasons for heightened security concerns around Douglas, who was transferred to a UK prison along with his brother Justin Ramoon, amid allegations they were planning an armed jail break. The brothers were also alleged to be orchestrating criminal activity from behind bars.

An affidavit from Governor Martyn Roper, submitted in court proceedings last year, pinpoints Douglas’s relationship with Nina White among numerous factors that raised his risk profile.

Roper’s evidence suggests the romantic entanglement between Douglas and the former senior manager in the Cayman Islands Prison Service could allow the convicted killer to access sensitive information about other inmates.

“There are serious concerns about Ms. White and Mr. Douglas’s relationship,” he stated.

“Ms. White would have had access to personal/private information about her clients (prisoners) and potentially staff. There is a concern that she may share this information with Mr. Douglas.”

Excerpts from the governor’s affidavit are included in a written court judgment from Acting Justice Michael Wood, following an April 2021 Grand Court hearing dealing with aspects of a human rights challenge from the two prisoners, which contested the decision to transfer them to the UK. The relationship between Douglas and White was ongoing at the time of that judgment, and she was supplying cash and exchanging calls with both defendants, according to Roper’s evidence.

Wood rejected the brothers’ request that the transfer be reversed, in part because of an earlier court ruling that determined that no process existed in Cayman, for sensitive evidence supporting the governor’s decision, to be properly scrutinised.

The judgment was not made public at the time and was only released last week, along with an earlier judgment in the ongoing case, during a Court of Appeal hearing on the issue.

Douglas and Ramoon argue, among other things, that the decision to transfer them to the UK violated their rights to a private and family life, making it difficult for their Cayman-based relatives to visit them in prison.

The Governor’s Office has argued that the brothers, two of at least four ‘high-risk’ inmates known to have been transferred to the UK, present such a high risk to national security that they cannot be safely incarcerated in Cayman.

A $25,000-a-year fund has been set up to allow family members to visit them in England and they are allowed frequent phone calls and video calls, court papers indicate.

Much of the court proceedings to date have focussed on the determination of the Governor’s Office that the two men represent a threat to national security, as well as on their rights to contest that decision.

That determination was the basis of the original decision, signed off by the UK Foreign Office, to invoke the Colonial Prisoners’ Removal Act 1884 to transfer the two men out of the jurisdiction.

At an earlier preliminary hearing, the Governor’s Office was granted public interest immunity from divulging some of the evidence on which that decision was based. Lawyers for Douglas and Ramoon have questioned that immunity, saying it gives them no scope to challenge the case against their clients.

The absence of legislation allowing for closed-door hearings in Cayman – known as Closed Material Procedure hearings – in cases impacting national security, has further complicated matters.

Alleged links to Jamaican hitmen

Roper’s affidavit nonetheless summarises the gist of the case against the two men – that they represent a national security risk that rises above the level of normal criminality. It also indicates that informants or investigative methods could be jeopardised if the basis for that decision is presented in open-court hearings.

“The basis upon which the Plaintiffs were originally transferred to the United Kingdom in June 2017 (before I took up my post) was that they could not be safely detained at HMP Northward and that their activities presented a threat to national security. That is an assessment with which I agree,” Roper’s affidavit states.

“Despite their conviction and imprisonment, the Plaintiffs had continued to engage in serious criminal activity.

“Intelligence revealed that they had or were seeking to obtain high-powered automatic weapons; they had criminal associates with the knowledge and propensity to use them, including professional ‘hitmen’ brought by boat from Jamaica; a track record of murdering and attempting to murder gang rivals and witnesses; and of making threats of harm, including to a senior prison officer.”

The affidavit goes on to highlight evidence that the pair exercised control over other inmates and might have been able to influence prison officers through threats.

Roper adds, “It is reasonable to conclude that had the Plaintiffs remained in the Cayman Islands and had continued with their criminal activities on the same scale, they represented an actual or potential threat to the peace and security of this small island nation.”

Relationship with a prison officer

Details of Douglas’s relationship with White emerged in further evidence from the governor, relating to claims that the transfer had impacted the brothers’ constitutionally-protected right to a private and family life.

Lawyers for the Governor’s Office argued that the brothers have been afforded generous contact with friends and family, including regular calls and visits funded by the Cayman Islands government.

The evidence highlighted includes ongoing calls and payments to both men from White, whose contract with the Cayman Islands Prison Service was not renewed in 2017.

The governor’s affidavit indicates, “Both Mr. Ramoon and Mr. Douglas complain of a lack of funds for telephone calls. Ms. White has deposited a total of over £10,000 into the accounts of Mr. Douglas, Mr. Ramoon and 4 other prisoners.”

He goes on to highlight recent payments to both men and as many as 255 calls between Ramoon and a UK number used by White.

The exact nature of the governor’s concerns about the relationship between White and the prisoners is not detailed, though reference is made to the potential for her to share information about other inmates in HMP Northward.

White was at the centre of controversy during her time in Cayman. Another senior officer was suspended for planting a hidden camera in an air-conditioning duct in her office. Internal correspondence, reported in the Compass,  later revealed that the camera was planted “with a view to collecting evidence in relation to allegations of inappropriate behavior by Ms. White with prisoners”.

Speaking to the Compass following her departure from the role in 2017, White denied anything improper and claimed she was victimised and bullied during her time in Cayman.

“All I know is that a number of unfounded allegations were made [by two prisons staffers]… which were malicious and unfounded and were not – and could not – be supported by any evidence,” White said at that time.

Evidence under wraps

Much of the detail of the case against the two men is not spelled out in Wood’s or Justice Marlene Carter’s judgments, which are filled with legal arguments about the extent to which the governor’s case that the brothers present a national security threat can be subjected to scrutiny.

While there is now no dispute that Ramoon and Douglas were rightly convicted of the 2015 killing of Jason Powery outside the Globe Bar in George Town, their lawyers argue that they have not been given a fair chance to contest the determination that they present a threat to national security.

In this, their lawyers argue, their constitutional right to lawful, administrative decision-making has been impacted.

“The justification put forward for Public Interest Immunity assumes what is in dispute: that the Plaintiffs pose a risk that cannot be managed by the Cayman Islands’ Prison Service and other public authorities. That risk is not accepted,” said a brief summary of their arguments contained in the judgment.

Hugh Southey, QC, appeared for the brothers instructed by Prathna Bodden of Samson Law, and Laurence Aiolfi, of Mourant.

The consequence of Wood’s initial ruling was that the men remained in the UK. The Court of Appeal heard evidence in the case last week and is considering the next step.