Home Attorneys Kurt B. Fliegauf

Kurt B. Fliegauf

Kurt Fliegauf Headshot(2026)

Kurt represents clients in complex, high-stakes, and often high-profile business disputes.

With over 30 years of experience as a trial lawyer, Kurt has handled dozens of trials. His willingness to take a case to a verdict has consistently led to favorable outcomes for his clients. Known as a zealous advocate for his clients’ interests, Kurt is effective in resolving matters favorably.

Kurt is Co-chair of the firm’s Business Litigation and Insurance Litigation practice groups. He also is Chair of the firm’s Technology Committee. His practice focuses primarily on commercial disputes including complex claims such as conversion of trade secrets, deceptive business acts, and breach of contract. He frequently represents software companies, law firms, and closely held businesses in disputes involving allegations of breach of fiduciary duty and unfair business practices. Additionally, he has extensive experience in insurance coverage, representing both insurers and insureds in complex coverage disputes, including bad-faith claims.

A recognized expert in his field, Kurt secured a landmark Massachusetts Supreme Judicial Court decision establishing that Massachusetts Unfair Business Practices Act applies to business partners who unfairly compete with each other. His work on this case earned him Lawyer of the Year recognition from Massachusetts Lawyers Weekly in 2021. He also has a niche expertise in what he calls “SaaS gone sideways” claims, where software as a service providers fail to meet their contractual obligations for custom IT solutions. Kurt’s deep understanding of insurance coverage strategy is often a key factor in his litigation success.

Recognizing the need for skilled mediators in complex commercial matters, Kurt now leverages his years of experience to help parties resolve their disputes outside the courtroom. As a certified mediation neutral, Kurt brings a profound understanding of the intricate legal, financial, and often personal frameworks that define modern business disputes. His practice also is rooted in active listening and genuine empathy, ensuring that every stakeholder feels heard and understood. By combining a sharp analytical lens with a grounded, human approach, Kurt helps parties navigate the friction of conflict to reach a strategic, durable consensus.

In his free time, Kurt enjoys being in Narragansett, Rhode Island with his family and friends. He is an avid cyclist, often commuting by bike to work in Boston, and he enjoys rowing, kayaking, and fishing. Kurt also has a passion for the arts, having previously served as the chair of the board for the Hopkinton Center for the Arts.

Conn Kavanaugh: Common Pitfalls that Put Businesses in Litigation

Conn Kavanaugh: Whether a Business Should Pursue Litigation

How Can We Help?

Contact us today for a solution best suited to your legal needs.