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John Schwolsky is a partner in the Corporate & Financial Services Department and Co-Chair of the firm’s Chambers ranked Band 1 Insurance Transactional and Regulatory Practice Group. Mr. Schwolsky has extensive experience in insurance industry mergers and acquisitions. He also regularly represents issuers and underwriters in connection with securities offerings by insurance companies in the United States and overseas.

Chambers USA (2025) ranks Mr. Schwolsky in Band 1 for Insurance: Transactional & Regulatory (Nationwide and New York). He is also recognized by The Legal 500 U.S. as a Leading Lawyer (Hall of Fame) in the area of Insurance: Non-Contentious. Additionally, John was named "Lawyer of the Year" for Insurance Law (New York City) by Best Lawyers in America in 2026 and is recognized by the 2026 Lawdragon 500 Leading Dealmakers in America guide in Insurance Transactional.

Experience

Mergers and Acquisitions

In the area of mergers and acquisitions, Mr. Schwolsky’s assignments have included advising:

  • Aegon in its $9.7 billion merger with Transamerica
  • Aegon in its $3.2 billion merger with Providian, and related spin-off of Providian's non-insurance operations
  • Aegon in its $1.4 billion sale of Transamerica Re to Scor SE
  • Aegon in its $1.3 billion acquisition of Merrill Lynch's life insurance operations
  • Aegon in its acquisition of the group pension business of MONY
  • Aegon in its sale of Providian Property and Casualty Insurance Company
  • Aegon in its sale of Transamerica Financial Advisors, Inc. to John Hancock Financial Network
  • Aegon in the purchase of certain assets of Mercer HR Services LLC
  • Aegon in the sale of its two largest U.S. run-off businesses and certain related legal entities to affiliates of Wilton Re US Holding Inc.
  • Aegon in the formation of Dawn Re and the related reinsurance of its ULSG business
  • Allstate in connection with its approximately $4 billion merger with National General Holdings
  • Allstate in the approximately $4.0 billion sale of Allstate Life Insurance Company to entities managed by Blackstone
  • Allstate in the $2 billion sale of its Employer Voluntary Benefits business to StanCorp Financial Group
  • Allstate in its $1.43 billion merger with SquareTrade
  • Allstate in the $1.25 billion sale of its Group Health business to Nationwide
  • Allstate in its $1.2 billion merger with American Heritage Life Investment Corp.
  • Allstate in its $1.1 billion acquisition of CNA's personal lines business
  • Allstate in its $1 billion acquisition of Esurance from White Mountains
  • Allstate in its $740 million sale of Lincoln Benefit Life Company to Resolution Group
  • Allstate in its sale of Allstate Re to SCOR
  • Allstate in its sale of its variable annuity business to Prudential Financial
  • Allstate in the sale of Allstate Life Insurance Company of New York to Wilton Re
  • Allstate in its purchase of GE's Partnership Marketing Group
  • Assurant in its $2.5 billion acquisition of The Warranty Group
  • Assurant in the $940 million sale of its employee benefits business to Sun Life Financial
  • Assurant in its acquisition of American Title, Inc.
  • CNO Financial Group in the reinsurance of a substantial portion of its Long Term Care book to Wilton Re
  • CNO Financial Group in its $287 million sale of Conseco Life Insurance Company to Wilton Re
  • Corebridge Financial in its $2.8 billion individual retirement variable annuity transaction with Venerable and in its related sale of its SAAMCO asset management business to Venerable Holdings
  • Delek Group in its $290 million merger with Republic Companies Group
  • Special Committee of the Board of Directors of EMC Insurance Group Inc. in connection with Employers Mutual Casualty Company’s $356 million acquisition of all of the remaining shares of EMCI
  • Equitable Holdings, Inc. in the sale of its Corporate Solutions life reinsurance subsidiary and related agreement to reinsure a legacy variable annuity block (approximately $12 billion of general account reserves) to Venerable Holdings 
  • Equitable Holdings in the reinsurance to affiliates of Global Atlantic of a 50% quota share of pre-2009 group retirement VA contracts
  • Equitable Holdings in the reinsurance of 75% of its individual life insurance business to RGA for $2 billion including ceding commission and capital release.
  • Guardian Life in its strategic partnership with and minority investment in asset manager, HPS
  • Guardian Life in the reinsurance of a $7.4 billion variable annuity portfolio to Talcott Resolution Life
  • Homeowners of America, a Managing General Agent and insurance carrier hybrid, in its acquisition by Porch Group
  • Liberty Mutual in its $1.5 billion acquisition of Guardian Royal Exchange's US property and casualty business
  • Liberty Mutual in its purchase of the PRUPAC companies from Prudential Financial
  • Liberty Mutual in its renewal rights and reinsurance transactions with White Mountains Insurance Group
  • MetLife in its reinsurance of a $19.2 billion block of annuity and non-traditional life business to affiliates of Global Atlantic. 
  • MetLife in the separation of its U.S. retail business and spin-off of Brighthouse Financial, Inc., creating two independent, publically-traded companies
  • MetLife in its $16.4 billion acquisition of AIG's subsidiary, American Life Insurance Company
  • MetLife in its $11.8 billion acquisition of Citigroup's life insurance operations
  • MetLife in its $10 billion variable annuity risk transfer transaction with Talcott Resolution
  • MetLife in the sale of its national distribution sales force, MetLife Premier Client Group, to MassMutual
  • Pan-American Life Insurance Group in its merger with Mutual Trust Financial Group
  • Protective Life in its $1.06 billion acquisition of MONY Life
  • Sun Life Financial in its $650 million acquisition of Genworth's Employee Benefits Group Business
  • Sun Life Financial in its disposition of Clarica's US life insurance operations
  • Tower Group in its $550 million (including assumed debt) merger with ACP Re
  • Tower Group in its merger with Canopius Holdings Bermuda Limited
  • Tower Group in its strategic investment in Canopius Group Limited
  • Tower Group in its acquisition of One Beacon's personal lines insurance business
  • Tower Group in its acquisition of Hermitage Insurance Group
  • Union Central in connection with its merger with Ameritas Acacia and formation of UNIFI, a mutual life insurance holding company
  • Voya Financial, Inc. in the sale of its variable annuity and fixed and fixed indexed annuities businesses to an investor group including affiliates of Apollo Global Management LLC and Athene Holding, Ltd.
  • Voya Financial, Inc. in the sale of its life insurance operations to Resolution Life Group Holdings Ltd. for approximately $1.25 billion
  • An insurance holding company in its $525 million acquisition of an identity protection services company
  • A health insurance holding company in its sale to a national health insurance holding company

In addition, Mr. Schwolsky has advised on the following transactions:

Capital Markets

Mr. Schwolsky has advised issuers and underwrites in hundreds of securities offerings of investment grade debt, subordinated debt, surplus notes, preferred stock, common stock, and insurance linked securities by insurance companies.

* Mr. Schwolsky advised on some of these matters at his prior firm.

Credentials

Education


Cornell Law School, J.D. Yale University, B.A. (magna cum laude)

Bar Admissions


New York