Robert A. Kole

Rob Kole helps domestic and foreign insurers and reinsurers to achieve successful outcomes in some of the most significant, cutting edge issues affecting them, including opioids, mass shootings, terrorism, asbestos, environmental, food contamination, oil and gas, catastrophic property damage, and catastrophe bonds. Clients value the experience he brings in providing insurance and reinsurance advice, coverage opinions, litigation representation, arbitration guidance, and appellate work.

Rob has argued before the U.S. Court of Appeals for the First, Second, Fifth, Ninth, and Eleventh Circuits as well as the Connecticut Supreme Court and the California Court of Appeals in connection with insurance and reinsurance disputes. He has successfully litigated in the trial court, and affirmed on appeal, two of the earliest opioid coverage decisions in the U.S.: Travelers v. Anda (11th Circuit) and Travelers v. Actavis (California Court of Appeals); successfully litigated an issue of first impression in the Connecticut Supreme Court regarding insurance coverage for crumbling home foundations (Karas v. Liberty Mutual; Vera v. Liberty Mutual); successfully litigated in the trial court, and affirmed on appeal, the first dispute in the U.S. concerning coverage under catastrophe bonds (Mariah Re); and successfully arbitrated dozens of reinsurance disputes on behalf of ceding companies and reinsurers.

A number of Rob’s clients cannot be disclosed publicly due to the confidential nature of the proceedings. However, past or current clients in public matters include Liberty Mutual, Travelers, St. Paul, Swiss Re, Hartford, and American Family Insurance.

Rob is a member of Choate’s Executive Committee and serves as the Firm’s Assistant General Counsel.

Recognition

  • Best Lawyers in America (2017-2025)
  • Fellow of the American College Of Coverage And Extracontractual Attorneys
  • Chambers USA (2017-2024)
  • The Legal 500 (2012-2024)
  • “Litigation Star” by Benchmark Litigation
  • Named one of 10 “Insurance Law Rising Legal Stars Under 40” by Law360
  • Boston Magazine Top Lawyer in Insurance (2022)
  • Leading Lawyer for Insurance by Who's Who
  • World’s Leading Insurance and Reinsurance Lawyers by Who’s Who
  • Massachusetts Super Lawyers
  • Business Today “Top 10 Most Influential Insurance Lawyers in Massachusetts 2023”

Representative Engagements

  • Obtained successful judgments for insurers, both via trial and summary judgment, in connection with opioid claims asserted by municipalities.
  • Obtained summary judgment, affirmed by the Second Circuit Court of Appeals, on behalf of a ceding company in one of the first catastrophe bond litigations in the U.S.
  • Successfully briefed and argued appeals before the Eleventh Circuit and the California Court of Appeals regarding insurance coverage for opioid claims.
  • Successfully briefed and argued appeal in the Connecticut Supreme Court on an issue of first impression regarding the scope of “collapse” coverage under homeowners’ policies.
  • Obtained summary judgment, affirmed by the Fifth Circuit Court of Appeals in a matter of first impression, on behalf of an insurer in connection with a lawsuit seeking coverage for oil and gas claims.
  • Obtained summary judgment, affirmed by the First Circuit Court of Appeals, on behalf of an insurer in a matter of first impression involving the scope of personal injury coverage.
  • Obtained reversal by the First Circuit Court of Appeals of a summary judgment ruling against an insurer involving contribution claims.
  • Tried confidential reinsurance arbitrations involving environmental, asbestos and catastrophic property damage liabilities on behalf of cedents and reinsurers.
  • Tried confidential reinsurance arbitration involving World Trade Center losses on behalf of cedent.
  • Lead counsel for joint defense groups in connection with multi-party, multi-million dollar lawsuits involving insurance coverage for asbestos and environmental pollution claims.
  • Successfully resolved, through settlement, a variety of coverage litigations and multi-claim arbitrations.

Publications and Presentations

Professional and Community Involvement

  • Former special prosecutor for the Suffolk County District Attorney’s office, where Rob successfully tried (in both jury and bench trials) or plea bargained dozens of criminal matters
  • Group leader at ARIAS-US conferences on the subject of reinsurance arbitration
  • Serving as counsel for the International Rescue Committee with respect to a contract dispute, which resulted in litigation
  • Member of the Massachusetts Bar Association
  • Member of the Boston Bar Association

Education & Credentials

University of Virginia School of Law
JD, 1996
Lafayette College
BA, 1993, cum laude

Admissions

Massachusetts

U.S. District Court, Massachusetts

U.S. Courts of Appeals, First, Second, Fifth, Ninth, and Eleventh Circuits

Robert's Insights