OUR HISTORY

THE ENSTAR STORY

Beginnings

Enstar’s story began in Bermuda in 1993 with the launch of Castlewood Limited. Recognising the untapped potential in the reinsurance sectors’ overlooked run-off space, Enstar’s founders combined their expertise in risk and liabilities to offer pioneering services to the global (re)insurance industry. Their plan was to support client companies by taking on their discontinued operations and freeing up capital.

Enstar's founders realised that scale would be critical in their ability to deliver. Eight years and more than a dozen property/casualty legacy acquisitions later, they formed a joint venture called Castlewood Holdings Ltd. with continuing partners The Enstar Group, Inc. and Trident II LP, an investment fund then managed by Marsh & McLennan.

Castlewood built a reputation for disciplined, strategic deal-making, helping to shape the emerging run-off market with a series of innovative transactions. These centred around taking on legacy commitments from companies that were struggling with exposure to asbestos and other major catastrophe losses. Early transactions included deals with Wackenhut, Allied Domecq and Foster Wheeler.

Scaling

The success of this partnership led to increased scale and in 2001, JC Flowers and Stone Point Capital were brought into the fold as new shareholders, leading to larger transactions, including River Thames Insurance, Turegum and Gordian.

In 2007, Castlewood merged with Enstar Group, taking its name and listing on the Nasdaq stock exchange. This move supported continued growth via better access to public capital markets.

By 2013, Enstar was the largest standalone legacy reinsurance consolidator in the world, a position we continue to hold. While asbestos-related transactions have decreased, other opportunities, such as workers’ compensation and general liability, have emerged. Enstar has continued to develop innovative solutions to meet evolving client needs.

Pioneering Retrospective Solutions

The evolution of the run-off industry over the past 30 years has been significant. Enstar has played a pivotal role in shaping legacy as a mainstream part of the global insurance industry. Today, we continue to lead the way in delivering pioneering retrospective solutions – helping clients unlock capital, manage risk and simplify their books. Our success is grounded in a proven business model, global scale and deep operational expertise, which we apply to every transaction to deliver lasting value for our partners.

The Future

In 2025, Enstar embarks on its next chapter of growth following the take-private deal with global investment firm Sixth Street. We look to the future with confidence and optimism. We are determined to continue to lead the industry, living by the same values that have always driven the business.

Enstar continues to move from strength to strength and remains vigilant to opportunities where its innovative capital release solutions can realise value.