Jesse D. Crary

Jesse D. Crary

Shareholder / Director / Senior Vice President
Burlington VT, Washington DC

Posts by Jesse D. Crary

Micro-Captives & New IRS Settlement Offer

On September 16, 2019, the Internal Revenue…

Association Health Plans & Captives: New Regulations, New Opportunities

Attorney and shareholder Jesse Crary is scheduled…

Vermont's First Affiliated Reinsurance Company

In March 2019, Vermont State Officials announced…

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Jesse Crary concentrates his practice on captive insurance, commercial transactions, regulatory compliance and general corporate matters. Through his extensive work representing and advising captive insurance companies and risk retention groups, he has developed strong relationships with insurance regulators and leading captive service providers. Jesse is a specialist and leading attorney in the area of group medical stop loss captives.

Jesse helps clients develop integrated benefit programs that combine the administration of employee benefit plans with access to captive medical stop loss coverage, and provides valuable assistance navigating the complexities of insurance and benefits-related laws and regulations. Jesse has extensive experience forming and providing ongoing corporate and regulatory counsel to single parent, group, sponsored and protected cell captive insurance entities, as well as risk retention groups.


  • Vermont Law School, J.D. 2006
  • University of Vermont, B.A. 1996

Professional Affiliations

  • Vermont Bar Association
  • Vermont Captive Insurance Association Finance Committee

Admitted to Practice

  • Vermont Bar
  • U.S District Court for the District of Vermont
  • District of Columbia Bar

Pro Bono & Volunteer Work

  • United Way Workplace Ambassador
  • Head Coach, Richmond VT Little League

Speaking Engagements

  • Presenter, "Secret Agent(cy) Man"; VCIA Conference; Burlington, VT,; Aug. 8-10th, 2017
  • Presenter, “Efficient Legal Structures for Group Medical Stop Loss Captives;” Captive Insurance Conference of America 2015
  • Presenter, “Cell Captives: Uses and Best Practices;” Vermont Captive Insurance Association Conference 2015