Robert “Bob” Gilbert is a leading insurance recovery and commercial litigation attorney who helps policyholders secure coverage and enforce complex contractual rights.

For more than three decades, he has represented businesses across virtually every major industry, helping his clients to recover billions of dollars in insurance proceeds and dispute resolutions.

Bob advises clients on both pre-loss risk strategy and post-loss recovery, with a practice spanning the United States, Canada, Mexico, Western Europe, the Middle East and Asia. He is particularly known for handling high-stakes, multijurisdictional matters involving catastrophic losses, emerging risks and complex coverage disputes.

Representative Experience

  • Advised a major medical-projects manufacturer in the recovery of $800 million in flood and wind losses.
  • Represented a multinational safety mask manufacturer that successfully recovered more than $50 million in asbestos- and silica-related defense and settlement costs (United States District Court for the District of South Carolina and Queens Court, England).
  • Represented a major distributor of tobacco products in litigation against a $1.2 billion products liability/chapter 93A suit brought by the Commonwealth of Massachusetts to recover Medicaid expenditures for smoking-related illnesses and nearly 50 personal injury suits alleging smoking-related illnesses (Superior Court for the Commonwealth of Massachusetts).

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  • Business Interruption and First-Party Insurance Recovery
    • Represented five major event companies in the successful recovery of hundreds of millions of dollars in insurance proceeds for event cancellation and business interruption losses stemming from the COVID-19 pandemic.
    • Advised more than 120 U.S. and international companies on several billion dollars in pandemic-related business interruption matters, including entities in the entertainment, sports, hospitality, health care, manufacturing, private equity, higher education and technology industries.
  • Third-Party Liability Insurance Recovery
    • Represented a major manufacturer of compact discs, phonographic records, cassette tapes and toys in a successful litigation to obtain insurance proceeds from 22 insurers for defense costs and environmental liabilities.
    • Advised major regional banks, for their own account and on behalf of managed trusts, in insurance coverage, lending and other business disputes.
    • Represented a former chemical manufacturer in numerous successful lawsuits to obtain insurance coverage for defense costs, remedial costs and damages for personal injuries, including insurance proceeds recovered for claims arising from DDT contamination in Santa Monica Bay, Henderson, Nevada, and the Stringfellow Acid Pits in California.
    • Secured the recovery of hundreds of millions of dollars in insurance proceeds relating to environmental, asbestos, silicosis and other mass tort liabilities for major New England, American and international manufacturers.
    • Represented a multinational valve and flow control manufacturer to obtain environmental insurance from primary and excess insurers for up to $20 million in cleanup costs, defense costs, attorney’s fees and other damages arising out of two state-issued cleanup orders (successfully resolved in Superior Court for the Commonwealth of Massachusetts).
    • Secured insurance recoveries in excess of $100 million for investigative, defense and indemnity for cleanup costs for solvents contamination of groundwater for a leading uniform supply company (Massachusetts State and Federal Court).
    • Represented a major Midwestern manufacturer to successfully recover defense and environmental cleanup costs arising from five sites in four states (Illinois State Court and Indiana State Court).
    • Advised mutual fund and securities industry companies in obtaining directors and officers liability coverage for claims arising from securities law violations.
    • Successor to a major valve manufacturer litigation ultimately resulting in the recovery of more than $100 million in asbestos-related defense and settlement costs (Los Angeles, California Superior Court).
    • Advised a major tobacco company in a dispute over the application of a retrospective premium endorsement to long-tail environmental and product liability claims.
    • Represented a Massachusetts produce company in litigation to obtain return premiums under retrospectively rated workers compensation policies.
  • Complex Contract and Commercial Litigation
    • Advised international sports bodies, American and international sports leagues, franchises in the major professional sports leagues and some of the most recognizable American athletes in a wide spectrum of contract disputes involving media rights, collective bargaining and other complex, high-dollar disputes.
    • Represented publicly traded and privately held businesses involved in shareholder disputes.
    • Advised commercial, manufacturing and high-tech entities in trade secret and misappropriation of technology disputes.
    • Advised on renegotiation and breach disputes arising from force majeure events, including both pandemic-related non-performance, as well explosions, hurricanes, fires and other natural disasters.
    • Represented Northern New England’s largest marble and granite fabricator in numerous successful corporate, shareholder and non-competition litigations (Superior Court for the State of New Hampshire).
    • Advised a consortium of insurers in their successful constitutional challenge in the California Supreme Court to portions of Proposition 103, a voter-passed initiative which would have imposed confiscatory rate-setting standards on automobile, casualty and other insurers in California.

Professional Highlights

  • Chambers USA, Band 1 – Insurance: Policyholder – Massachusetts (2018–2025)
  • The Legal 500 U.S.,  Leading Partner – Insurance: Advice to Policyholders (2025)
  • Fellow of the American College of Coverage Counsel

Education

  • J.D., Harvard Law School, 1987
    cum laude

Admissions

  • Massachusetts

    California

    New Hampshire