Douglas L. Siegler

Douglas Siegler

Doug Siegler is co-chair of Venable's East Coast Estate Planning Group. Doug is a tax attorney who represents high-net-worth individuals on tax and wealth planning matters and focuses on wills, trust agreements, insurance, and charitable giving programs. He oversees all aspects of estate planning, including estate administration tasks and multigenerational wealth transfer strategies. He develops innovative approaches to structuring income, gift, and generation-skipping transfer tax planning. Doug also handles transfer tax planning for clients married to non-U.S. citizens, and to individuals living outside the United States.

Related Practices


Representative Matters

  • Reached a favorable settlement of an IRS gift tax audit regarding the proper valuation of several promissory notes, gifted by the taxpayer to her children and grandchildren. Also prevented the IRS from expanding the scope of the audit into an examination of the intrafamily sales of LLC interests that had given rise to the promissory notes
  • Advised an owner of pre-initial public offering (IPO) stock, regarding estate planning options, ultimately creating two GRATs and an irrevocable trust for young children, and preparing a federal gift tax return disclosing the gifts
  • Retained as special counsel for a surviving spouse in a long-running will dispute and IRS estate tax examination; advised the spouse and decedent’s estate of the necessity to create a QDOT to receive a marital bequest, preparing the QDOT document, and negotiating with the IRS to confirm qualification of the trust as a QDOT
  • Advised a foreign national on gift, estate, and generation-skipping transfer tax opportunities, prior to immigration to the United States, including gifting opportunities, appropriate location of trust vehicle, and best assets to be used for funding of gifts
  • Implemented post-mortem tax planning, including qualified disclaimers, and balancing the size of the taxable estates of a husband and wife, who died within a few days of each other, resulting in a substantial reduction in state estate tax liability and better utilization of decedents’ available generation-skipping transfer tax exemptions




  • J.D. with honors Duke University School of Law
  • B.A. cum laude Princeton University

Bar Admissions

  • District of Columbia
  • Maryland

Professional Memberships and Activities

  • Fellow, American College of Trust and Estate Counsel 
  • Past chair, Estate and Gift Taxes Committee, Tax Section, American Bar Association 
  • Member and past director, District of Columbia Estate Planning Council
  • Member, Duke University Estate Planning Council
  • Former member, Governing Board, St. Albans School, Washington, DC
  • Former board member, Concord Hill School; Chevy Chase, Maryland


  • The Best Lawyers in America, 2006 – 2016, 2018 – 2022, 2024
    • Lawyer of the Year, 2019
  • Chambers High Net Worth
    • Private Wealth Law, Washington, DC, 2017 – 2023
    • Private Wealth, Eastern Region, USA, 2017 – 2013
  • Chambers USA, Wealth Management, Nationwide, 2010 – 2015
  • Euromoney, The World’s Leading Trusts and Estates Practitioners, 2009
  • Super Lawyers, Washington, DC, 2007 – 2015, 2017 – 2023
  • Washingtonian, Top Lawyers Hall of Fame, 2022