Jack Caynon is one of the most seasoned healthcare and business attorneys in the Pacific Northwest. He spent 15 years as in-house counsel for several large health systems across the country. Jack enjoys working with hospitals and physician practices, as well as physician and nursing clients. His experience is very broad – he has represented clients on both sides of acquisition/sales transactions, formed health institutes, represented clients in compliance matters and provided business and regulatory advice to nonprofit hospitals and independent medical practices.

My experience as in-house counsel allows me to understand that working closely with the leadership of an organization requires quick, practical advice in a cost-effective manner.

  • Represented physician in a successful case seeking to enjoin a non-compete under the unclean hands doctrine
  • Acted as lead counsel in representing client in an ani-kickback investigation by the DOJ and achieved a favorable outcome for the client.
  • Conducted successful asset purchase transaction for the client to purchase the assets of a medical practice.


  • Medicaid Lookback Rules and Planning, National Business Institute (2023)

Professional Affiliations

  • American Bar Association
  • American Health Lawyers Association
  • Oregon State Bar Health Law Section

Community Affiliations

  • Oregon Rocketry Club – President


I am an avid “rocketman.” I fly high power rockets in the High Desert. Some of my rockets are more than 10 feet long and have reached altitudes over thirty thousand feet. I also teach rocket construction at a local college to students pursuing degrees that will help them soar into the high frontier.