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Robert Tomilson

fax +1 215.640.8501

Robert Tomilson is a member of the firm’s Insurance and Reinsurance practice and co-chair of the firm’s Ai and Emerging Technologies practice. Robert represents insurers, reinsurers, insurtechs, brokers, and other intermediaries in litigation, arbitration (foreign and domestic), and regulatory investigations. He establishes offshore carriers as U.S. E&S carriers, creates MGUs, MGAs, insurance agencies, and captive reinsurance entities. Robert advises on regulatory inquiries and internal and insurance department investigations. Robert’s reinsurance experience includes:  yearly renewal term (YRT), Jumbo Limits, toxic tort, property CAT, group disability, professional sports disability, variable annuity, surety, and other products.


Robert sits on the Board of Trustees at the Collegium Institute and Eastern University as well as the Advisory Board at Drexel University Kline School of Law. Robert was an advisor to the Restatement of the Law (Liability Insurance) and teaches Insurance Law & Regulation at Drexel University Kline School of Law. Robert has been recognized by Best Lawyers, Who’s Who Legal (Insurance and Reinsurance) and published in Crain’s Business, Bloomberg News, Risk & Insurance, and maintains his own podcast, Insurtech, Briefly.


J.D., Washington University School of Law, St. Louis, Missouri
M.A., University of Illinois at Urbana-Champaign, Champaign, Illinois
B.A., University of New Hampshire-Main Campus, Durham, New Hampshire


Named among Best Lawyers in America® for Insurance Law (2018-2024), Litigation-Insurance (2023-2024) by Best Lawyers

Who’s Who Legal – Insurance & Reinsurance (2019)


AIDA Reinsurance and Insurance Arbitration Association

Eastern University, Board of Trustees

Drexel University, Thomas R. Kline School of Law, Advisory Board

Drexel University, Thomas R. Kline School of Law, Adjunct Professor of Insurance Law

Restatement of the Law: Insurance Liability, Advisor

The Anthony J. Drexel Society

The Circle of the New Criterion

State Bar Licenses

Pennsylvania, District of Columbia, Maryland, New York
  • Lead counsel for carrier in arbitration against four excess and a catastrophe layer of liability reinsurance involving more than $100M mass tort claims.
  • Represented health care carrier in $40M medical stop arbitration with Plan sponsor, included allegations of improper calculation of Plan premium and ex gratia payments to beneficiaries.
  • Lead counsel for an MGA in a four-state Insurance Department investigation regarding unlicensed activity and excessive fees.
  • Lead counsel for an actuarial firm before the Securities and Exchange Commission as well as in SDNY class action, wherein the allegations included the insufficiency of a public company’s loss reserves.
  • Lead counsel in London-situs arbitration, where testimony and documents produced in the United States, involving the experience account balance of more than $25M for a property catastrophe excess, finite retrocession agreement involving 9-11 risks.
  • National and coordinating counsel for excess workers comp carrier providing coverage for self-funded employers in all fifty states.
  • Established a Delaware-domiciled risk purchasing group (an RPG) for a 14,000-member trade association for the purchase of liability insurance on a group basis.
  • Represented Tokyo-based international insurer in establishing a reinsurance syndicate that allowed it to cede certain carved out risks under general liability policies.
  • Provided a comprehensive “insurable interest” opinion for a transaction raising $100M wherein life policies were used as collateral for bondholder commitments.
  • Represented a reinsurer before the Pennsylvania Supreme Court on the right of set-off among multiple contracts with an insolvent Pennsylvania insurer.
  • Represented Barbados-based reinsurer in transaction wherein a $300M dividend was made to North American and parental guarantees provided to cedents.