Robert A. Whitney

Boston, MA


Robert A. Whitney

Boston, MA


With more than 25 years of experience in complex insurance coverage, bad faith, reinsurance, regulatory affairs and compliance, and commercial litigation, Robert A. Whitney represents insurers and reinsurers to resolve disputes throughout New England, including coverage and bad faith disputes in state and federal courts in Massachusetts, Maine, New Hampshire, Rhode Island, New Jersey and Pennsylvania, and throughout the country. His experience includes negotiating resolution of coverage claims and counseling insurance company clients on claims litigation strategy and procedure and coverage questions.

Rob has advocated for ceding companies and reinsurers in reinsurance litigation and arbitration, navigating disputes encompassing diverse insurance coverage and bad faith claims. He possesses arbitration experience with facultative certificates and treaty programs, offering counsel to both ceding and reinsuring companies regarding their rights and obligations.

Rob previously served as the Corporate Secretary for the Stonewall Insurance Company and Seaton Insurance Company, as well as on the Board of Directors of the Transport Insurance Company. He was the former Deputy Commissioner and General Counsel of the Massachusetts Division of Insurance for four years, where he provided legal counsel to the Commissioner of Insurance, as well as the Governor’s Chief Counsel and Chief of Staff and other senior administration officials, concerning the interpretation and application of state and federal insurance laws and regulations. In his current role, Rob now provides legal counsel to clients regarding the application of federal and state regulations to insurance and reinsurance companies, as well as advice to responses to requests for information from regulatory agencies, external auditors and others concerning regulatory requirements. He also appears before regulatory agencies to help clients resolve any regulatory and compliance issues and to facilitate regulatory approvals. Rob also partners with senior executive management to provide guidance on legal and regulatory matters related to company operations and products, including the preparation of legal memoranda concerning significant legal, compliance and regulatory matters.

Robert has extensive involvement in the legal community, and frequently shares his knowledge by authoring articles and manuals. He also presents at a number of regional and national conferences, including those sponsored by DRI, ABA, National Association of Insurance Commissioners, LexisNexis, Mealey’s Publishing, MCLE, the Boston Bar Association, ACI, Arias-US, the Massachusetts Insurance and Reinsurance Bar Association and many others.

Practice Areas


Insurance Coverage

Reinsurance

Curriculum Vitae


Education (2)
  • Boston University Law School (JD, G. Joseph Tauro Scholar)
  • Brown University (BA, with honors)
Professional Memberships (4)
  • Boston Bar Association (Former Member, Civil Rights and Civil Liberties)
  • Boston Lawyer Chapter of the American Constitution Society (President and Co-Founder)
  • Massachusetts Insurance and Reinsurance Bar Association (Board Member; Former President)
  • DRI (Chair, Reinsurance Law Group)
Bar Admissions (6)
  • Massachusetts
  • Maine
  • US District Court, District of Massachusetts
  • US District Court, Central District of Illinois
  • US Court of Appeals, First Circuit
  • US Supreme Court
Certifications (1)
  • Certified Insurance and Reinsurance Arbitrator, ARIAS-US
Awards (4)
  • The Best Lawyers in America© - Insurance Law (2022-2025)
  • Boston Magazine "Top Lawyer" in Insurance Law (2023-2024)
  • Massachusetts "Governor's Citation" for 20 Years of Dedicated Service to Persons with Disabilities
  • Commonwealth of Massachusetts Citation for Outstanding Performance as Leader of Health Insurance Reform Implementation Team, Division of Insurance
Publications (2)
Presentations (10)
  • Some Basics of Reinsurance Right-to-Associate & Claim Control Clauses
    Co-Authored with Alexander G. Henlin, DRI Magazine - Covered Events (December 2021)
  • Transitioning to a New View: Coming to See Health Insurance Coverage for Gender Dysphoria in a New Light
    Connecticut Insurance Law Journal, Volume 25, Issue 2 (Spring 2019)
  • Massachusetts Liability Insurance Manual
    Co-Editor, MCLE 3rd Edition (2017)
  • Insurance Regulation, Chapter 14, Massachusetts Liability Insurance Manual
    MCLE 3rd Edition (2017)
  • Insurance Coverage for Employment-Related Practices, Chapter 18, Massachusetts Liability Insurance Manual
    MCLE 3rd Edition (2017)
  • Shadow Insurance
    Massachusetts Insurance & Reinsurance Bar Association Newsletter (Winter 2018)
  • Aftermath: The Legal Community’s Response to the Boston Marathon Bombings
    Boston Bar Journal, Volume 58, Number 1 (January 7, 2014)
  • Review of the Insurance Implications of the New Animal Control Law
    Massachusetts Agent Newsletter (February 7, 2013)
  • When Does an Arbitration Panel Exceed its Authority in Issuing Awards? Some New Cases Take a Look
    Massachusetts Insurance & Reinsurance Bar Association Newsletter (Winter 2012)
  • Retakaful: Reinsurance in the World of Islam
    ARIAS-US Quarterly (2011)
Community Involvements (4)
  • Beacon Hill Civic Association (Former Chair; Former Board Member)
  • Boston Groundwater Trust (Co-Chair; Trustee; Treasurer; Former Board Member)
  • Suffolk University Institutional Master Plan Task Force (Member)
  • Boston Community Preservation Committee (At-Large Member)