Anne J. O'Brien

Anne J. O'Brien: Attorney with Caplin & Drysdale, Chartered AV stamp icon
  • Member at Caplin & Drysdale, Chartered (67 Attorneys)
  • One Thomas Circle NW, Suite 1100, Washington, DC 20005
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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.

Awards & Rankings

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
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; Top Lawyer, 2004-Present
Who's Who Legal, Leading Practitioner, 2015
Fortune Magazine, Women Leaders in the Law, 2014
Legal Week, International Trusts and Private Client Elite, 2012
Legal Times, Leading Lawyer, 2004

Recent Publications

• UPDATED: Year-End Charitable Giving Ideas: IRA Rollovers and Bunching Charitable Deductions, with Beth Shapiro Kaufman, William D. Fournier, Megan E. Wernke, and Alison F. Egan, Caplin & Drysdale Client Alert, November 28, 2018
• IRS Adds Foreign Trust Information Reporting to Compliance Campaign Program, with Arielle M. Borsos, Victor A. Jaramillo, Kirsten Burmester, and Dianne C. Mehany, Caplin & Drysdale Client Alert, June 1, 2018

(republished in Global Tax Weekly )

• 2018 Ushers In New Estate Planning Opportunities and Pitfalls, with Beth Shapiro Kaufman, Megan E. Wernke, and Alison F. Egan, Caplin & Drysdale Client Alert, January 18, 2018
• Possible Repeal of the Estate Tax in 2017, with Beth Shapiro Kaufman, Megan E. Wernke, and William D. Fournier, Caplin & Drysdale Client Alert, December 5, 2016
• Tax Plans Compared (December 2016) Individual Income Tax, with Beth Shapiro Kaufman and Jonathan S. Brenner, Caplin & Drysdale Client Alert, December 5, 2016
• 2016 Federal and State Estate Gift Tax Exemptions for D.C., Maryland, and Virginia, with Beth Shapiro Kaufman, Megan E. Wernke, and William D. Fournier, Caplin & Drysdale Client Alert, December 28, 2015
• Maryland Estate Tax Exemption Set to Rise, with Megan E. Wernke, William D. Fournier, and Beth Shapiro Kaufman, Caplin & Drysdale Client Alert, May 16, 2014
• 2014 Estate Planning: Should I Take Advantage of Portability?, with Beth Shapiro Kaufman, Caplin & Drysdale Client Alert, December 23, 2013
• Letters of Wishes and Protectors as Devices to Further the Settlor's Purposes, A Guide to International Estate Planning, American Bar Association, 2nd Ed., January 1, 2013
• No Time Like the Present for Gifting: Tax Relief Act Planning Opportunities, Advisory, February 8, 2012
• Federal Estate and GST Tax Repeal, Advisory, January 19, 2010
• Wealth Transfer Strategies for Turbulent Times, Advisory, December 9, 2008

Recent News

•Caplin & Drysdale Honors the Women of the Firm, Caplin & Drysdale, March 8, 2019
•Accounting Today Quotes Beth Kaufman and Anne O'Brien on IRS Chief Rettig's Potential Response to Trump Tax Investigation, Accounting Today, October 4, 2018
•Caplin & Drysdale Improves Ranking in 2019 Best Lawyers in America , August 15, 2018
•Caplin & Drysdale Attorneys Advance in Chambers Ranking for Private Wealth Law, Chambers High Net Worth Guide, July 23, 2018
•2018 Legal 500 Distinguishes 18 Caplin & Drysdale Attorneys, Firm Renews Top-Tier Firm Ranking for Tax Controversy, The Legal 500, May 31, 2018
•18 Caplin & Drysdale Attorneys Recognized by Super Lawyers in D.C., April 23, 2018
•Anne O'Brien and Clark Armitage Listed Among Top 30 U.S. Lawyers by Euromoney, Euromoney Expert Guides, March 2, 2018
•Chambers Lists Caplin Lawyers as Leaders in Private Wealth Law, Chambers High Net Worth Guide, September 15, 2017
•Caplin & Drysdale Earns Top Ranking in 2018 Best Lawyers in America , August 15, 2017
•7 Caplin & Drysdale Lawyers Listed as Leaders in Their Field by Expert Guides, Expert Guides, July 25, 2017
•Caplin & Drysdale Lawyers Listed Among D.C.'s Most Prominent Practitioners, Super Lawyers, April 27, 2017
•Beth Kaufman and Anne O'Brien Named Leading Women in Business Law for Trusts and Estates, Expert Guides, September 8, 2016
•Best Lawyers in America Lists 18 Caplin & Drysdale Attorneys, U.S. News & World Report, August 15, 2016
•Caplin & Drysdale Attorneys Listed as Leaders in Their Field for Private Wealth Law, Chambers High Net Worth Guide, June 24, 2016
•Three Caplin Lawyers Distinguished by Best Lawyers, Business Edition of Best Lawyers, June 21, 2016
•Super Lawyers Recognizes Caplin & Drysdale Lawyers from Several Practice Areas, Super Lawyers, April 26, 2016
•Patricia Lewis and Anne O'Brien Named in 2016 Best of the Best Global Ranking, Expert Guides, April 5, 2016
•Washingtonian Names Beth Kaufman and Anne O'Brien Among 2016 Top Wealth Advisers, The Washingtonian Magazine, March 21, 2016
•U.S. News & World Report Quotes Anne O'Brien on Advice Financial Advisors Give Their Clients, U.S. News & World Report, January 29, 2016
•Anne O'Brien Named a Leading Practitioner in Who's Who Legal, Who's Who Legal, December 23, 2015
•Washingtonian Names Caplin & Drysdale Attorneys Among Washington's Top Lawyers, November 19, 2015
•Caplin & Drysdale Lawyers Listed Among World's Leading Women in Business Law, Expert Guides, July 28, 2015
•Clients and Peers Distinguish Caplin & Drysdale in Chambers' Rankings, Chambers USA, May 19, 2015
•Super Lawyers Lists Caplin & Drysdale Lawyers, Caplin & Drysdale, April 23, 2015
•Beth Kaufman and Anne O'Brien Named Top Estate Attorneys in Washingtonian Magazine, The Washingtonian Magazine, October 30, 2014
•Fortune Lists Caplin & Drysdale Lawyers Among Leaders in the Law, Fortune Magazine, October 6, 2014
•Caplin & Drysdale Lawyers Chosen as The Best of the Best USA for 2014, September 16, 2014
•Caplin & Drysdale Lawyers Earn Best Lawyers Ranking, August 21, 2014
•Guide to World's Leading Women in Business Law Lists Caplin & Drysdale Lawyers, Expert Guides, July 29, 2014
•Clients and Peers Recommend Caplin & Drysdale in 2014 Legal 500 Ranking, The Legal 500, July 1, 2014
•Caplin & Drysdale Earns Top Honors in 2014 Chambers USA, Chambers USA, May 28, 2014
•The Washington Post Lists Caplin & Drysdale Attorneys Among the Top Attorneys in D.C., The Washington Post, April 30, 2014
•Washingtonian Recognizes Caplin & Drysdale Attorneys Among Washington's Best Lawyers, Washingtonian Magazine, December 3, 2013
•Caplin & Drysdale Lawyers Listed in World's Leading Women in Business Law, Expert Guides, November 8, 2013
•Caplin & Drysdale Enhances Tax Practice with Three Lateral Hires, Caplin & Drysdale, October 1, 2013

Areas of Practice (3)

  • Private Client
  • International Tax
  • Exempt Organizations

Education & Credentials

Contact Information:
(202) 862-5033  Phone
University Attended:
University of New Mexico, B.A., 1967; The George Washington University, M.B.A., 1976
Law School Attended:
American University Washington College of Law, J.D., magna cum laude, 1988
Year of First Admission:
1989, District of Columbia; 1988, Maryland

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
•Chair, International Estate Planning Committee
•Chair, International Membership Committee
•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


Peer Reviews

  • 5.0/5.0
  • A Martindale-Hubbell Peer Rating reflects a combination of achieving a Very High General Ethical Standards rating and a Legal Ability numerical rating.

*Peer Reviews provided before April 15, 2008 are not displayed.

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