Benjamin Kralstein is a Partner in Simpson Thacher’s Mergers and Acquisitions Practice, where he is a member of the Insurance Transactional and Regulatory team. Based in New York, Ben’s practice focuses on advising U.S. and non-U.S. insurers, reinsurers, insurance markets, agents, managing general agents, reinsurance intermediaries, investors and financial institutions in a broad range of transactional and regulatory matters in the insurance and reinsurance industry. Ben has extensive experience advising clients on domestic and cross-border reinsurance transactions and related collateral arrangements, sidecar transactions, PRT transactions, mergers and acquisitions, structured finance solutions, insurance securitizations and capital markets transactions.
Over the course of his nearly 15-year career, Ben has represented some of the largest clients in the insurance industry, including Canada Life, Cigna, Fidelity & Guaranty, Global Atlantic, Munich Re, Nationwide, Pacific Life, Prosperity Life, Somerset Re and SCOR, and has been involved in numerous landmark transactions.
Notable experience prior to joining Simpson Thacher includes advising:
M&A Transactions
- Somerset Reinsurance on its sale of a controlling interest to Aquarian Holdings, as well as a commitment for further growth capital
- Cigna Corporation in the international insurance and healthcare regulatory matters associated with its $67 billion acquisition of publicly traded Express Scripts Holding Company; and terminated sale to Anthem, Inc. in a transaction valued at $54.2 billion
- Wells Fargo in the sale of its Iowa-based insurance companies, Centurion Life Insurance Company and Centurion Casualty Company
- A leading investment manager and its affiliated Bermuda reinsurance company in the acquisition of an insurance and annuity company
Sidecar Transactions
- Teachers Insurance and Annuity Association of America (TIAA) in its strategic transaction with Symetra Life Insurance Company involving the launch of Mariner Re Ltd., a Class E licensed reinsurer domiciled in Bermuda, which will be supported by a $750 million equity investment from TIAA*
- Midwest Holding and its insurance subsidiaries in the structuring and sale of multiple Vermont domiciled incorporated cell sidecars
- Golub Capital as lead investor in a new life and annuity sidecar reinsurer, Ruby Reinsurance Company, with Reinsurance Group of America as sponsor
- A lead investor in a new life and annuity sidecar reinsurer, Ivy Re III, with Global Atlantic as sponsor
- A lead investor as bidder in a $750+ million sidecar
- A Bermuda reinsurance company and its affiliated investment manager in the formation and capitalization of a long duration, on-demand capital sidecar vehicle
- A Bermuda reinsurance company in the structuring and sale of Bermuda domiciled life and annuity sidecar reinsurer
- A global financial institution as lead arranger for a credit facility supporting a reinsurance sidecar transaction
Reinsurance
- Somerset Reinsurance on its reinsurance transaction with Prudential Financial, Inc. to reinsure approximately $12.5 billion of reserves backing Prudential's guaranteed universal life policies issued by Pruco Life Insurance Company and Pruco Life Insurance Company of New Jersey
- Somerset Reinsurance on a number of its portfolio reinsurance deals
- Knighthead on a number of its portfolio reinsurance deals
Ben’s work has put him in the spotlight by Chambers USA – most recently ranked as “Band 5” attorney (2026) and previously ranked as an “Up and Coming” attorney (2024 – 2025) and an “Associate to Watch” (2021 – 2023). Clients have praised his “depth of technical knowledge in the insurance and reinsurance landscape” and that he is “dedicated and has such expansive knowledge” of the industry.
Ben also has a broad pro bono practice in which he advises pro bono clients on a variety of matters, including U.S. asylum applications, uncontested divorce cases and corporate governance and formation matters.
Ben received his J.D., cum laude, from St. John’s University School of Law in 2013. While attending St. John’s University School of Law, he was an Associate Managing Editor for the St. John’s Law Review and interned at the Securities and Exchange Commission’s Division of Enforcement. He received his B.S. from Indiana University in 2010. He is admitted to practice in New York and New Jersey.
*Completed at Simpson Thacher.