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Joshua D. Headley

Joshua D. Headley


Washington, DC
Alexandria, VA
Philadelphia, PA

How Josh Helps Clients

Josh serves as Counsel in the Tax, Wealth and Succession Planning, and Nonprofit Organizations groups. His primary focus is advising high net worth individuals on sophisticated estate planning matters including mitigating death taxes. Josh also regularly works with executors and trustees on large, complex trust and estate administration and tax compliance matters. On the nonprofit side, Josh works closely with private individuals and large charitable institutions in structuring and operating planned giving vehicles, including private foundations (operating and grant-making) and public charities. 

In 2022, Josh became an active volunteer with Wills for Heroes (WFH), a non-profit organization providing essential legal documents free of charge to the nation’s first responders, including wills, living wills, and powers of attorney.

What Clients Can Expect

A friendly demeanor, responsiveness and hard work are the cornerstones of Josh’s practice style. He enjoys helping people navigate complex issues by distilling what matters most to them to make an informed decision.

There is no better feeling than helping make your client’s goals become a reality, whether it be a legacy for their loved ones or some other noble cause.

Outside the Office

Josh grew up in the Shenandoah Valley of Virginia. He is the descendant of four generations of furniture makers. To his surprise, Josh discovered that the practice of law was his calling. He lives in Virginia with his wife, Caroline, and three children, Maisie Lee, August and Louisa.

Proof Points

  • Developed a comprehensive estate plan for successful real estate developer that included restructuring numerous business entities to reduce estate taxes, avoid probate and provide for the seamless transition of business operations to the next generation.
  • Advised fiduciaries in the administration of multimillion dollar estate, including navigating the probate process and tax compliance matters relating to asset protection trusts, insurance trusts and other dynasty trusts.
  • Advised board of directors of public charity with multibillion-dollar endowment regarding the adoption of new investment policies in light of recent changes in charitable laws.
  • Established employee relief fund for national retailer including advising on formational and governance matters and obtaining recognition of tax-exempt status from the IRS.
  • Received a 2021, 2022 and 2023 Best Lawyers: Ones To Watch recognition for Tax Law.
  • Named to the Washington, D.C. Super Lawyers Rising Stars® list in 2022.