A Florida billionaire who ran a failed investment company on the island has pleaded guilty to conspiracy to commit offences against the United States and conspiracy to commit money laundering in connection with a scheme to defraud insurance regulators and policyholders through a web of companies based in Bermuda, North Carolina, Malta and elsewhere.

The US Justice Department said: “According to court documents, from no later than 2016 through at least 2019, Greg Lindberg, 54, of Tampa, conspired with others to defraud various insurance companies, other third parties and ultimately thousands of insurance policyholders.

“Lindberg and others conspired to deceive the North Carolina Department of Insurance and other regulators, evaded regulatory requirements meant to protect policyholders, concealed the true financial condition of his companies, and improperly used insurance company funds for his personal benefit.

“Lindberg and his co-conspirators caused companies he controlled to invest more than $2 billion in loans and other securities with his own affiliated companies and laundered the proceeds of the scheme.

“As set forth in the indictment, Lindberg directed the scheme and personally benefited from the fraud in part by ‘forgiving’ more than $125 million in loans to himself from the insurance companies that he controlled.

“To carry out the conspiracies, Lindberg and others engaged in circular transactions among Lindberg’s web of entities using insurance company funds and made and caused to be made various materially false and misleading statements and representations to and omitted material information from regulators, various ratings agencies, insurance companies, insurance policyholders and others regarding these transactions.

“As a result of Lindberg’s conduct, his insurance companies, third-party entities and policyholders suffered substantial financial hardship, and some of his insurance companies have been placed in rehabilitation and liquidation.”

Mr Lindberg is known on the island because his Global Bankers Investment Group in 2018 acquired Northstar Financial Services (Bermuda), which later went into liquidation.

Principal deputy assistant attorney-general Nicole Argentieri, head of the Justice Department’s Criminal Division, said: “Greg Lindberg and his co-conspirators misused $2 billion of company funds in their international scheme to defraud corporate victims, regulators and policyholders.

“Thousands of policyholders suffered substantial financial hardship as a result of Lindberg’s fraud scheme, which left multiple companies in or on the brink of liquidation. The Justice Department will not hesitate to hold corporate executives accountable when they threaten critical sectors of the economy, like the insurance industry, to enrich themselves.”

The Justice Department said Mr Lindberg pleaded guilty to one count of conspiracy to commit offences against the United States, including wire fraud, investment adviser fraud, and crimes in connection with insurance business, and one count of money-laundering conspiracy.

He faces a maximum penalty of five years in prison on the conspiracy to commit offences against the United States count and ten years in prison on the money-laundering conspiracy count.

On May 15, after a retrial, Mr Lindberg was convicted by a federal jury in Charlotte of conspiracy to commit honest services wire fraud and bribery concerning programmes receiving federal funds for orchestrating a bribery scheme involving independent expenditure accounts and improper campaign contributions, aimed at bribing the elected North Carolina Commissioner of Insurance to influence the regulation of Mr Lindberg’s insurance companies.

A sentencing date has not yet been set. A federal district court judge will determine Mr Lindberg’s sentence in both cases after considering the US Sentencing Guidelines and other statutory factors in each case.

Mr Lindberg was remanded in custody of the US Marshals.