Michael Stern is a partner in the Corporate & Financial Services Department and a member of the Insurance Transactional and Regulatory Practice Group. Michael focuses on corporate transactions in the insurance industry, including mergers and acquisitions, and insurance and reinsurance regulatory matters.


Prior to joining Willkie in 2019, Michael was counsel at Debevoise & Plimpton LLP.

Michael has advised on the following significant matters*:

  • Arch Insurance North America on its $450 million acquisition of Allianz’s U.S. MidCorp and Entertainment insurance businesses
  • Prudential Financial, Inc. on its agreement to reinsure a $12.5 billion guaranteed universal life block with Somerset Re
  • Prudential Financial, Inc. on its agreement to reinsure a $10 billion block of variable annuities with an affiliate of Constellation Insurance Holdings, Inc.
  • Delaware Life Insurance Company in its sale of Delaware Life Insurance Company of New York to Nassau Financial Group
  • Sixth Street in its insurance platform Talcott Resolution’s agreement to reinsure $25 billion of liabilities from Principal Financial Group
  • Sixth Street in its agreement alongside Resolution Life to reinsure a $35 billion fixed index annuity portfolio of Allianz Life
  • The underwriters in Argo Group International Holdings, Ltd.’s issuance of $150 million depositary shares in July 2020
  • Spinnaker Insurance Company, a licensed national property and casualty insurer, in its acquisition by Hippo Insurance Services
  • Zurich in its agreement to sell its U.S. Corporate Life and Pensions (Group Benefits) business to Aflac
  • Bain Capital Private Equity and Diamond Castle in the sale of Beacon Health Options to Anthem
  • Principal Financial Group in its $1.2 billion acquisition of an Institutional Retirement & Trust business
  • The Carlyle Group in its strategic partnership with AIG to position DSA Re as a platform to provide solutions for insurance liabilities globally
  • MAPFRE Insurance in its agreement to provide Safeco Insurance the opportunity to underwrite its personal lines policies in the states of Indiana, Kentucky and Tennessee
  • American International Group in its $5.56 billion acquisition of Validus Group, a Bermuda-based, NYSE-listed, (re)insurance company
  • AmTrust Financial Services in a strategic transaction with Madison Dearborn for a portion of AmTrust’s U.S. fee businesses valued at $1.15 billion
  • American International Group in the sale of its medical stop-loss operations to Tokio Marine HCC
  • Canada Pension Plan Investment Board in its $1.1 billion acquisition of Ascot from American International Group
  • J.P. Morgan Securities and Morgan Stanley, as financial advisors to American International Group, in its $3.4 billion sale of United Guaranty Corporation, the leading private mortgage insurance company in the United States, to Arch Capital Group
  • Swiss Re Corporate Solutions in its $153 million acquisition of IHC Risk Solutions and its direct employer stop loss business from Independence Holding Company
  • Protective Life Insurance Company in its acquisition by reinsurance of a block of term life insurance business from Genworth Financial
  • Sun Life Financial in its acquisition of Assurant’s Employee Benefits business
  • Stone Point Capital in its significant equity investment in specialty insurance broker Alliant Insurance Services, with KKR retaining a significant equity investment in the business
  • HC2 Holdings in its acquisition of American Financial Group’s long-term care businesses
  • Morgan Stanley, as financial advisor to Pan-American Life Mutual Holding Company, in its merger with Mutual Trust Holding Company
  • Harbinger Group and its subsidiary Front Street Re, in the acquisition of Ability Re by way of a merger of Ability Re with and into Front Street Re, with Front Street Re as the surviving entity
  • Prudential Financial in its acquisition of a 40% interest in Administradora de Fondos de Pensiones Habitat, a leading provider of retirement services in Chile, for a total purchase price of approximately $550 million

* Michael advised on some of these matters prior to joining Willkie.



Harvard Law School, J.D., 2009 Brandeis University, B.A., 2005

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New York