Andrew R. Holland

ANDREW HOLLAND leads the U.S. insurance regulatory practice within Sidley’s M&A and Private Equity group. His practice is concentrated in the representation of insurance companies, insurance intermediaries, and institutional investors with respect to insurance regulatory and corporate matters.

He has a broad range of experience, including corporate transactions, enforcement matters, corporate governance, licensing of insurers, insurance holding company act issues, financial examinations and statutory accounting matters, producer compensation, and non-admitted insurance, and has also advised numerous insurtech startups and sharing economy companies with respect to insurance regulatory matters.

“Andrew provides clear and definitive advice based on his experience.”
Chambers USA 2025

Strong guidance of his clients has earned Andrew recognition in Chambers USA for Insurance: Transactional & Regulatory—New York (2016–2025). In past editions, clients noted that he is “fantastically knowledgeable, with deep understanding and technical depth” (2018) and that “people come to him with their thorniest issues” (2019). In the 2022 edition, Andrew has been described by clients as “an excellent regulatory lawyer, in particular in regard to New York insurance regulatory issues.”

Andrew serves on the Board of Governors of the Association of Life Insurance Counsel. Prior to joining Sidley, Andrew was senior vice president and general counsel of the U.S. property-casualty insurance operations of American International Group, Inc. (AIG).

Examples of Andrew’s experience include representation of:

• Medica, a Minnesota-based nonprofit health plan with more than 1.4 million members across nine states, in its definitive agreement to acquire key contracts and assets of UCare.
• Mubadala Capital with respect to insurance regulatory matters as the lead investor in Aquarian Capital’s take-private of Brighthouse Financial, Inc. (Nasdaq: BHF), an all-cash transaction valued at approximately US$4.1 billion (pending).
• Apollo Global Management on insurance regulatory matters in its acquisition of Bridge Investment Group in an all-stock transaction with an equity value of approximately US$1.5 billion (pending).
• New Enterprise Associates (NEA) on insurance regulatory matters in the take-private acquisition by an NEA affiliate of NeueHealth at an enterprise value of approximately US$1.3 billion (pending).
• The Fortegra Group, Inc., a U.S.-based specialty insurer, in connection with its US$1.65 billion sale to DB Insurance Co., Ltd.
• National Life Group on insurance regulatory matters in connection with a US$4.9 billion flow and block annuity reinsurance transaction with 26North.
• The Cigna Group on insurance regulatory matters in the sale of its Medicare businesses and CareAllies to Health Care Service Corporation for a total transaction value of approximately US$3.7 billion.
• National Western Life Group, Inc. on insurance regulatory matters in its US$1.9 billion acquisition by an affiliate of Prosperity Life Group.
• RenaissanceRe Holdings, Ltd. on insurance regulatory matters in connection with its US$2.985 billion acquisition of Validus Reinsurance Ltd. from American International Group, Inc.
• Nassau Financial Group, a Golden Gate Capital portfolio company, on insurance regulatory matters in the acquisition of Delaware Life Insurance Company of New York.
• American National Insurance with respect to insurance regulatory matters in its US$5.1 billion acquisition by Brookfield Asset Management Reinsurance Partners. 
• TowerBrook Capital Partners, L.P. on insurance regulatory matters in the US$586 million acquisition of ProSight Global, Inc.
• Athene Holding on insurance regulatory matters in its merger with Apollo Global Management, in an all-stock transaction creating a pro forma US$29 billion market cap company (with Athene valued at approximately US$11 billion).
• An investor consortium led by Cornell Capital, LLC, Atlas Merchant Capital LLC, TRB Advisors, LP, Global Atlantic Financial Group, Pine Brook, J. Safra Group, and The Hartford on insurance regulatory matters in the sale of Talcott Resolution to Sixth Street.
• Venerable Holdings, Inc. in its acquisition of Corporate Solutions Life Reinsurance Company from Equitable Holdings, Inc. and the reinsurance of approximately US$26 billion of reserves from Equitable Financial Life Insurance Company.
• Sirius International Insurance Group in its strategic merger with Third Point Reinsurance, creating a US$3.3 billion company.
• Cigna Corporation in the sale of its group life and disability insurance business to New York Life Insurance Company, the largest mutual life insurer in the United States, for US$6.3 billion.
• Fortitude Re, a premier provider of retroactive reinsurance and legacy run-off management solutions located in Bermuda, in the US$2.2 billion sale of a majority interest to New York-based The Carlyle Group and Tokyo-based T&D Holdings.
• Athene Holding, Ltd. on insurance regulatory matters in its US$1.55 billion combination common share exchange with and sale of common shares to Apollo Global Management LLC. The transaction also involved the elimination of Athene’s multi-class share structure.
• Apollo Global Management, LLC on insurance regulatory matters in connection with its US$2.6 billion acquisition of publicly traded Aspen Insurance Holdings Limited.
• The Navigators Group, Inc. on insurance regulatory matters in connection with its definitive agreement to be acquired by The Hartford Financial Services Group, Inc. in an all-cash transaction that values Navigators at approximately US$2.1 billion.
• Apollo Global Management, LLC on insurance regulatory matters with respect to the acquisition of Catalina Holdings (Bermuda), Ltd.
• Apollo Global Management, LLC on insurance regulatory matters in connection with the acquisition of Fortress Investment Group’s ownership in OneMain Financial for US$1.4 billion.
• Cigna Corporation on insurance regulatory matters with respect to its acquisition of Express Scripts Holding Company, a transaction valued at US$67 billion.
• Athene Holding, Ltd. and Apollo Global Management LLC in connection with the acquisition of Voya Financial, Inc.’s Closed Block Variable Annuity segment and its individual fixed and fixed indexed annuity business.
• Cigna Health and Life Insurance Company in connection with a Consent Order with the New York Department of Financial Services with respect to small group health insurance.
• Markel Corporation in connection with its US$919 million acquisition of State National Companies, Inc.
• PartnerRe Ltd. in connection with the CAD375 million acquisition of Aurigen Capital Limited.
• Cigna Corporation on insurance regulatory matters with respect to its terminated acquisition by Anthem, Inc., a transaction valued at US$54.2 billion.
• Lyft, Inc. as defendant in litigation with the New York Department of Financial Services and New York Attorney General regarding alleged violations of New York insurance law.
• Athene Holding, Ltd. in connection with its US$1.55 billion acquisition of Aviva plc’s U.S. life insurance and annuity businesses and the concurrent sale of the life insurance business to Global Atlantic Financial Group.
• Transatlantic Reinsurance Company in connection with U.S. insurance regulatory issues relating to the restructuring of its UK branch operations in contemplation of Solvency II.