Caroline Trusty advises clients across a range of industries in complex litigation and appellate matters, with a particular strength in developing clear, strategic legal arguments that are both persuasive in court and accessible to her clients. She is frequently recognized for her concise and effective legal writing, which her clients value for its clarity and practical application to their business goals. Caroline has significant experience in state and federal trial and appellate courts, where she regularly argues dispositive motions and appeals. In addition to her courtroom advocacy, she counsels clients in pre-litigation matters, including drafting demand letters and other communications aimed in resolving disputes efficiently and favorably outside of court. She also works with labor and employment clients in conducting sensitive internal investigations and employment-related pre-litigation disputes. Caroline’s practice spans a wide range of substantive areas, from employment and contract disputes to insurance coverage, fiduciary obligations, tax, and regulatory challenges, demonstrating her versatility and strategic insight across multiple practices. Caroline is also strongly committed to pro bono representation, particularly in matters related to housing. Recognition The Legal 500: Rising Stars (2024-2025) Representative Engagements Represents a major insurance company in high-stakes, multi-party litigation involving insurance coverage for opioid-related claims in both federal and state courts. Represented an employer in a successful summary judgement appeal before the Massachusetts Appeals Court in an employment-related dispute. Represented a pharmaceutical company in securing summary judgement in a commercial litigation matter before the Massachusetts Superior Court. Advised a reinsurer in appellate briefing before the U.S. Court of Appeals for the Second Circuit in a complex reinsurance dispute. Represented a corporate client in drafting a motion to dismiss in federal court in California involving ERISA and common law fiduciary standards. Represented a national retail company in the Delaware Court of Chancery in a contract and licensing dispute and subsequent contract negotiations. Advised a pharmaceutical company in preparing mediation statements for multiple pre-litigation employment-related matters. Represents an investment manager in ongoing state tax disputes. Represents pro bono clients in Massachusetts state court in civil matters, including housing-related disputes. Professional & Community Involvement Active participant in Choate’s legal clinics through the Lawyers Clearinghouse Education & Credentials Harvard Law School, JD (2017) Harvard College, BA (2014) cum laude; The Harvard Crimson, Executive Design Editor Admissions District of Columbia Massachusetts U.S. District Court, District of Massachusetts Clerkships Honorable Robert N. McDonald, Maryland Court of Appeals