A consortium of 14 top hoteliers in Jamaica, the Cayman Islands, Bahamas and Florida are suing a London-based insurance broker for €10m after they were defrauded out of millions following a ‘grossing up’ scam by a former employee.

The Evening Standard reported that Charles O’Sullivan, nicknamed ‘the Pirate of the Caribbean”, conned one hotel out of of $150,000 by unfairly charging a concealed fixed fee on top of a $406,000 brokerage.

A Lloyd’s of London tribunal found O’Sullivan guilty on three counts of discreditable conduct in March 2017, and he was declared “unfit and unsuitable”, banned and ordered to pay £138,698 in costs, cut by £10,000 on appeal, and only avoided a fine because of the impact of being suspended from his £350,000-a-year job.

Lloyd’s said in a market bulletin: “Mr O’Sullivan knew the deception would enable his company to retain far more by way of remuneration than the assured were prepared to allow… dishonestly obtaining remuneration by deception.”

O’Sullivan ran the scam at Lloyd’s brokerages Besso, where he worked from 2004 to 2011, and at Bennett Gould & Partners (BG & P) until he was fired for gross misconduct in 2012.

In 2018, O’Sullivan declared himself bankrupt and flew to Spain before BG & P was awarded £1.2m in damages against him for misrepresentation by a High Court judge.

Judge David Waksman said: “It is plain… there was serial and knowing misrepresentations by Mr O’Sullivan concerning the income and client representations. He obviously knew what he had done previously amounted to being dishonest, although he purports to deny that now.”