White Mountains’s Sale of Esurance and Answer Financial Businesses to Allstate

On February 26, 2026, Bishop Street Underwriters (“Bishop Street”), a RedBird Capital Partners portfolio company, announced that it has completed a strategic structured capital investment of $125 million by White Mountains Insurance Group, Ltd. (“White Mountains”). Cravath is representing White Mountains in connection with the transaction.

On October 3, 2025, White Mountains Insurance Group, Ltd. (“White Mountains”), a Bermuda-domiciled financial services holding company, announced that it has signed a definitive agreement to sell a controlling interest in Bamboo, a data-enabled insurance distribution platform, to funds advised by CVC Capital Partners (“CVC”) in a transaction that values Bamboo at $1.75 billion. White Mountains expects the transaction will result in a gain of approximately $310 to its book value per share and net cash proceeds of approximately $840 million. White Mountains will retain an approximately 15% fully-diluted equity stake in Bamboo post-closing, valued at $250 million based on the transaction. Cravath is representing White Mountains and Bamboo in connection with the transaction.

On July 18, 2025, BroadStreet Partners (“BroadStreet”), a leading middle-market insurance brokerage, announced the successful closing of a strategic investment by an investor group led by Ethos Capital, British Columbia Investment Management Corporation and White Mountains Insurance Group, Ltd. (“White Mountains”). Accounts advised by T. Rowe Price Investment Management, Inc. also participated. Ontario Teachers’ Pension Plan will retain a significant co control stake in BroadStreet and continue its partnership with the Ethos-led investor group. Cravath is representing White Mountains in connection with the transaction.

On July 7, 2025, White Mountains Insurance Group, Ltd. (“White Mountains”), a Bermuda‑domiciled financial services holding company, announced it has entered into an agreement to acquire a majority stake in Distinguished Programs (“Distinguished”), an MGA and program administrator for special property & casualty insurance. White Mountains will acquire approximately 50% of Distinguished’s outstanding equity interests for $230 million, which will result in White Mountains holding a 51% controlling interest in Distinguished following the closing of the transaction. Cravath is representing White Mountains in connection with the transaction.