Search Our Website:
Joshua D. Headley

Joshua D. Headley


Nonprofit Organizations Practice Group Leader

Washington, DC
Alexandria, VA
Philadelphia, PA

How Josh Helps Clients

Josh serves 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. He 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. He is the leader of the firm's Nonprofit Organizations Practice Group.

Josh co-chairs Buchanan's C.A.R.E.s Affinity Group, which supports employees who are caregivers or working parents, and is a member of the firm’s pro bono committee. In addition to his involvement within the firm, he is an active volunteer with Wills for Heroes. This noteworthy nonprofit organization provides 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.

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.
  • Coauthored "Tax Management Portfolio No. 452-2nd, Tax-Exempt Organizations — Reporting, Disclosure, and Other Procedural Aspects," which was published in Bloomberg Tax. This publication provides insight into various procedural rules applicable to federal income tax-exempt organizations under the Internal Revenue Code.
  • Recognized by Best Lawyers: Ones To Watch in the area of Tax Law since 2021.
  • Named to the Washington, D.C. Super Lawyers Rising Stars® list since 2022.

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.