Joshua D. Headley

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 also practices fiduciary litigation and regularly represents corporate and individual fiduciaries and beneficiaries in trust and estate-related disputes.

Josh co-chairs Buchanan's C.A.R.E.s Affinity Group, which supports employees who are caregivers or working parents. In addition to his involvement within the firm, he is very active in his local community, serving on the boards of several nonprofits in addition to other volunteer work. 

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 worthy 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 boards of directors of multiple charities regarding legal and tax hurdles associated with combination into a single entity.
• Represented a large nonprofit in cy pres action before the attorney general and state court affecting a significant charitable endowment.
• 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.
• Shepherded a private foundation through the process of converting to a public charity.
• Coauthored Tax Management Portfolio Nos. 488-2^nd, Fiduciary Duties of Nonprofit Directors and Officers and 452-2nd, Tax-Exempt Organizations — Reporting, Disclosure, and Other Procedural Aspects," which are published in Bloomberg Tax. These publications provide insight into governance and procedural rules applicable to federal income tax-exempt organizations.  
• 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.