Exclusive Structuring and Placement Agent Ark in the Formation Outrigger Re Ltd.

Ark Insurance Holdings Limited (“Ark”) announced the formation of Outrigger Re Ltd. (“Outrigger”)

• Outrigger is a Bermuda segregated accounts company registered as a Special Purpose Insurer
• Outrigger provides collateralized reinsurance to Ark Bermuda’s global property catastrophe portfolio
  • Collateralized reinsurance provided via a quota share
• Received $250 million in initial investor commitments
  • White Mountains committed $205mm of capital
  • Additional third-party investors include Aquiline & a subsidiary of Enstar Group Limited (NASDAQ: ESGR)

Outrigger represents an opportunity to provide scarce CAT capacity in a rapidly evolving marketplace

• Allows Ark to meet the needs of its current and future clients in a challenged market
• Provides Ark with an opportunity to take advantage of positive market dynamics
• Diversifies Ark’s sources of funding, increasing financial and operational flexibility

Ark is a specialty property and casualty insurance and reinsurance company

• Underwrites a diversified and balanced portfolio of reinsurance and insurance business
• Ark’s Bermuda platform, rated “A” by A.M. Best, commenced trading in January 2021
• Ark Syndicate Management Limited manages the underwriting of Lloyd’s Syndicates 4020 and 3902
• White Mountains owns 72% of Ark on a basic shares outstanding basis(a)

HTCMA acted as Exclusive Structuring and Placement Agent to Ark

• Provided advice through all stages of the process, driving an optimal outcome for Ark
• Identified a variety of institutional investors interested in supporting Ark through this transaction
• Key aspects of the transaction led by HTCMA included:
  • Development of the structure and economic terms of the transaction
  • Construction of a robust financial model including stochastic analysis of investor returns
  • Drafting of detailed marketing materials and assistance with investor due diligence requests
  • Selection and introduction of a wide range of global institutional investors
  • Coordination of the legal and regulatory aspects of the establishment of Outrigger

(a) As of the time of the transaction.