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Joshua D. Headley

Joshua D. Headley


Washington, DC
Alexandria, VA

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. Josh also regularly works with fiduciaries on trust and estate administration and tax compliance matters. On the nonprofit side, Josh works closely with donors and charitable institutions in structuring planned giving vehicles.

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.    

A lawyer’s sole purpose is to provide the assistance the client wants the lawyer to provide within the budget the client wants to pay.

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 now lives in Alexandria, Virginia with his wife, Caroline, and three children, Maisie Lee, August (“Gus”) and Louisa (“Lola”).

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 a multimillion dollar estate, including navigating the probate process and tax compliance for asset protection trusts, a life insurance trust and a revocable trust.
  • Coordinated the establishment of 501(c)(3) and 501(c)(4) organizations for the prevention of cruelty to animals. Worked with founder to navigate complex federal and state tax compliance matters and implement proper governance procedures.
  • Received a 2021 Best Lawyers: Ones To Watch recognition for Tax Law.