A pioneering business head who saw the island’s potential to build reinsurance into the international business pillar of its economy arrived in Bermuda at a defining moment for the industry.

Henry Keeling, a British underwriter, joined the trailblazing catastrophe reinsurer Mid-Ocean Re in January 1993, just months after Hurricane Andrew slammed into Florida as a Category 5 storm in the summer of 1992.

Andrew was then the costliest and most destructive storm to hit the state, and its knock-on effect was the catalyst that began Bermuda’s property catastrophe reinsurance market, with Mid-Ocean leading the pack.

Mr Keeling not only proved key to the company’s success, but made a point of developing Bermudian talent, and was a strong advocate for the island as a business haven.

Brian O’Hara, the former president and chief executive officer at XL — which acquired Mid-Ocean for $2.1 billion — said: “We helped start the first dedicated property catastrophe company, Mid-Ocean, back in 1992, when demand soared.”

XL was among the deep-pocketed sponsors of the company, which brought in Mr Keeling, then a deputy underwriter for Syndicate no. 51 at Lloyd’s of London.

Mr O’Hara said: “He was one of the early leaders of reinsurance here. Hurricane Andrew had an amazing impact of the world catastrophe market.

“Henry became a market leader, not only in property catastrophe reinsurance but general reinsurance. He did a terrific job and was very well respected.

“He built up a fine organisation of people who are still thriving in the industry.

“Henry was very highly regarded, and was a very close friend along with his wife, Jan.”

Greg Hendrick, chief executive at Vantage Risk, said Mr Keeling hired him into Mid-Ocean in 1995 — when friends and colleagues thought he was taking a risk.

“People asked if I was sure I wanted to give up a career in the States and go to Bermuda. Henry had left a very successful syndicate and set out at a time when others were turning their noses up at Bermuda, particularly London.”

Mr Hendrick described it as “a leap of faith”.

“The island had not regained its footing as a reinsurance market and was still licking its wounds from some of its failures in the 1980s.”

He said Mr Keeling, along with the late Michael Butt, was adept at building Mid-Ocean’s market as well as building the company.

“He wanted to show that Bermuda was not only a great place to underwrite but a true peer of New York and London in being a reinsurance place of excellence.”

Mr Hendrick recalled the company’s gatherings at the start of each day, nicknamed “morning prayers”, when Mr Keeling proved “challenging but constructive” in the review of the company’s underwriting.

“He had a willingness to be strong, but a coach as well.”

The company’s innovations included “the novel idea” of underwriting the state of California’s earthquake insurance.

Mr Hendrick said Mr Keeling was “thoughtful, very analytical, and incredibly well read, which was part of what made Henry such a fascinating guy — he had so many other interests outside of the reinsurance world”.

Mr Keeling became a chief operating officer at XL, achieving “great things across different parts of the company that we are all very grateful for”.

“A great husband and a great father. He will be missed.”

Mr Keeling had two children, Amanda and Christopher.

Jamie Veghte, former chief executive of reinsurance at XL, recalled Mr Keeling’s fondness for Taunton School where he boarded from an early age, in part because his father’s job in the Royal Navy meant the family moved frequently.

He said Mr Keeling never attended university but went straight from school into the insurance market.

“He was very, very intelligent and well read. Henry not only fit with the business community but he really made sure he understood Bermuda’s culture and way of life.

“He worked in Japan early in his career and picked up lessons that he applied to Bermuda — you fit in and learn local customs.”

Mr Veghte added: “He could be viewed as a pioneer, being at the forefront of that very important period in the development of Bermuda’s insurance market.

“The other strand of it was that he worked very hard to make sure we developed Bermuda talent in the organisation. You have some very prominent people in the insurance market that Henry hired and developed.”

He said Mr Keeling “took a big risk” in following his ambitions to Bermuda — but even after getting hired by Mid-Ocean, he waited until his colleagues at his Lloyd’s syndicate had made it through the company’s renewal season.

“It was a gamble for him. None of us knew how it was going to work. Bermuda was not that big of a reinsurance market.

“Then Mid-Ocean Re was a wildly successful company. It was a very important development for Bermuda.”

Mr Veghte added: “I had been in New York for my entire career, and Henry recruited me to come join the company. I got there about ten months after he did.

“It was the best decision I ever made, a very exciting period in the history of Bermuda’s insurance market.”

The two worked together until Mr Keeling retired from XL in 2008. The following year, he took on the role of president and chief executive of international operations at Guy Carpenter.

He held directorships at a string of firms in Bermuda and Britain, and from 2015 served as chairman of the board of governors for Taunton, where a memorial service is planned for next April.

A statement said: “His dedication and affection for the school was enormous, epitomised by his continued devotion, energy and commitment over the last several years, even whilst managing his illness.

“In a typically gracious and moving resignation letter, Henry commented that ‘serving on the Board of Governors has been one of the most important and rewarding things that I have done in my life.’

“Henry selflessly served the community not only as governor and chair but also in his extremely generous support of both means tested funding for deserving and ambitious pupils and essential capital projects.”

• Henry Charles Vaughan Keeling, a top reinsurance executive and chief operating officer at XL, was born on March 12, 1955. He died on November 22, 2023, aged 68