Anne O'Brien is a well-regarded and highly-skilled trust and estate practitioner who joined Caplin & Drysdale as a Member in 2013.  

The cornerstone of Ms. O'Brien's practice involves advising domestic and international private clients on safeguarding their personal and business interests.  She offers counsel on matters relating to estate planning, trust and estate administration, and related areas of federal and state tax law. These areas include transfers of family wealth to succeeding generations, settlement negotiations in large estate controversies, family trust matters, and charitable tax planning. Additionally, Ms. O'Brien assists high-net-worth individuals (HNWIs) and families in structuring their U.S. and global holdings, as well as the transfer of those holdings to family members, trusts, charitable organizations, and other entities.


As a fellow of the American College of Trust and Estate Counsel (ACTEC) and an academician of The International Academy of Estate and Trust Law, Ms. O'Brien is among an exclusive group of lawyers uniquely qualified to help clients preserve their assets on a global scale. Her noteworthy matters include:

  • Counsel various members of a wealthy multinational family with respect to structure and ownership of assets, premarital planning, expatriation issues and general estate planning.
  • Coordinate probate proceedings for and Internal Revenue Service (IRS) audit of a large estate with significant assets held in trusts involving multiple jurisdictions in both common and civil law countries.
  • Represent a large Washington, D.C., estate in an IRS audit involving conservation easement and valuation issues in connection with closely-held business assets.
  • Prepare private letter ruling request for trustee of large marital trust to address concerns that distributions from the trust will be treated as a disposition under Section 2519 of the Internal Revenue Code.
  • Represent U.S. beneficiary's interest in Swiss estate involving Swiss succession, Lichtenstein foundation and BVI trusts.
  • Prepare comments to proposed revenue ruling on private trust companies and meeting with IRS on behalf of private bank.
  • Counsel Isle of Man trust company in matter involving appropriate characterization of trust for which it was a trustee and contribution thereto.
  • Advise large Florida estate involving closely-held business assets with underlying real property interest subject to lawsuit initiated by nephews of decedent (settled by mediation).
  • Represent numerous wealthy estate planning clients, including multinational and U.S. families owning family holding companies (family limited partnership and family limited liability companies), closely-held businesses held through tiered corporate and partnership structures and real estate assets.

Admissions & Education

Bar & Court Admissions
  • District of Columbia
  • Maryland

J.D., American University Washington College of Law, 1988, magna cum laude

M.B.A., The George Washington University, 1976

B.A., University of New Mexico, 1967

Recognitions & Noteworthy

Honors & Recognitions
  • Chambers High Net Worth Guide, Private Wealth Law, D.C. and USA: Eastern Region, 2016-Present
  • Chambers USA, 2011-2012, 2014-2016
  • The Legal 500, Recommended, 2014, 2015, 2018-2020, 2022-Present
  • Best Lawyers in America, Women in the Law, Trust and Estates, 2016; Listed 2006-Present
  • Super Lawyers, Top 50 Women, 2008; Washington, D.C., 2008-Present
  • Expert Guides' World's Leading Women in Business Law, 2013-Present
  • Expert Guides' The Best of the Best, Trusts and Estates, 2014
  • Expert Guides' Trusts and Estates Practitioners, 2009
  • The Washingtonian, Top Money Advisers, 2014; Top Wealth Advisers, 2016; Best Financial Advisers, 2019; Lifetime Achievement Lawyer, 2022; Top Financial Advisers Hall of Fame, 2023; Top Lawyer, 2004-Present
  • Who's Who Legal, Private Client, Recommended, 2015, 2020-Present
  • Fortune Magazine, Women Leaders in the Law, 2014
  • Legal Week, International Trusts and Private Client Elite, 2012
  • Legal Times, Leading Lawyer, 2004

Professional Activities & Affiliations

Professional Activities
  • Member, Board of Trustees, Mills College in Oakland, California
  • Academician, The International Academy of Estate and Trust Lawyers
  • Member, American Bar Association, Section of Taxation and Section of Real Property, Trust and Estate Law
  • Fellow, American College of Trust and Estate Counsel (ACTEC)
  • State Chair, District of Columbia, 2008 - 2013 
  • Chair, International Estate Planning Committee, 2009 - 2013 
  • Chair, International Membership Committee, 2009 - 2012
  • Member, DC Estate Planning Council
  • Member, Tax Management Estate, Gifts, and Trusts Advisory Board
  • Past Chair, Estates, Trusts and Probate Section, District of Columbia Bar
  • Founding Board Member, National Center for Family Philanthropy
  • Advisory Board Member, William Wendt Center for Loss and Healing

Newsroom & Publications

Speaking Engagements
  • Anne O'Brien Discusses Closely Held Entities ACTEC Fall Meeting 
    11.04.2022 | Hotel Fairmont San Francisco
  • Anne O'Brien Analyzes Key Tax and Organizational Challenges for Closely Held Businesses at Mid-Atlantic Fellows Institute 
  • 09.12.2019 | New York, NY
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