F. Hale Stewart

F. Hale Stewart is a captive insurance professional and attorney with nearly two decades of experience designing and supporting captive insurance programs. He advises organizations across complex and high-risk industries—including trucking, energy, manufacturing, and professional services—on risk financing strategies that address rising premiums, limited market availability, and situations where strong risk management efforts are not fully reflected in insurance renewals.

Hale’s work focuses on helping companies evaluate whether self-funding through captive insurance is appropriate and, if so, how to structure programs that align with their operational risks and long-term financial goals. His approach, outlined in his book Designing a Risk Financing Program, is highly structured and detailed. It involves reviewing key organizational and risk-related documents, interviewing leadership and operational personnel, and preparing a comprehensive written analysis that identifies risk exposures, strengths and weaknesses in existing risk management practices, and opportunities for alternative risk financing. This process typically takes two to four months.

Prior to joining Dickinson Wright, Hale served in senior captive insurance development and legal roles, providing leadership in building captive insurance teams, drafting internal compliance materials, negotiating agreements with captive service providers, and supporting captive programs on tax, regulatory, and contractual matters. He has also represented clients in captive insurance audits and disputes, including responding to IRS information requests, developing audit defense strategies, and supporting litigation through legal analysis, motion practice, and trial record review.

Earlier in his career, Hale owned and operated his own law practice, where he concentrated on captive insurance for more than a decade. During that time, he formed, consulted on, or advised more than 50 captive insurance companies and programs; prepared feasibility studies and insurance policies; drafted corporate and governance documents; assessed existing structures for captive viability; and regularly advised on ongoing compliance matters. His earlier practice also included small business representation, litigation, and asset protection.

Hale is a widely published author on captive insurance and related tax issues. His work includes U.S. Captive Insurance Law and Captive Insurance in Plain English, as well as numerous articles analyzing captive insurance case law, IRS enforcement trends, risk distribution, and anti-avoidance theories. He has also contributed to leading federal tax law treatises and continues to write on emerging legal and regulatory developments affecting captive insurance programs.