Caplin & Drysdale is known for sophisticated tax planning strategies. The firm’s well-regarded group of trusts and estates attorneys are strong on complex domestic and international planning. “Everyone I have dealt with at that firm has been top-flight. Not only on the inbound planning for clients but also in expatriation work, which is an extremely complex area of the law.” Market Commentator, Chambers HNW

Our Private Client Group counsels individuals and families on domestic and cross-border tax and estate planning issues, including the use of trusts, partnerships, corporations, foundations and wills and the application of tax treaties. We also represent domestic and international clients in disputes with the IRS regarding their income, estate, gift, and generation-skipping transfer tax liabilities. We help individuals with their tax compliance issues, including pre- and post-immigration issues for international clients. We are one of the few firms with a focus on expatriation. Our attorneys draw upon their vast experience both in private practice and in government service to bring a uniquely informed perspective to our representations. 

Areas of Focus

Trust and Estate Planning 

The design of an estate plan and its implementation is at the core of any estate planning practice. Caplin & Drysdale attorneys know how to listen to clients, how to explain tax consequences in understandable terms, and how to prepare complex wills, trusts, and related documents. We work with high-net-worth individuals and families, both domestic and international, family offices, business owners, and trust and estate fiduciaries. We delight in crafting personalized estate plans to reflect a client’s particular values and meet family needs. Caplin & Drysdale Private Client attorneys are regularly recognized as the top professionals for their ability to develop sophisticated, flexible estate plans that can adapt to an ever-changing tax environment. We enjoy working as part of a team with our clients’ accountants, financial advisers, and other professionals to ensure proper reporting and seamless implementation of their estate plans. Our goal is to establish long-term relationships with clients, engaging throughout the years to counsel our clients in light of changing personal and legal circumstances.

Business and Succession Planning for Owners of Closely-Held Companies

Often the client’s most important asset is a closely-held business. Family businesses, in particular, present many complex issues involving the relationships among family members who work in the business and those who don’t, as well as key employees, all of whom have different perspectives, goals and financial pressures. Each family is unique, and we have deep experience in developing strategies within the client’s broader estate plan that address many different transitions such as changes in leadership, intergenerational succession planning, liquidity events, and when desirable, exit strategies. The Private Client group helps clients minimize taxes by seeking appropriate valuations of business interests, establishing trusts and entities to facilitate lifetime giving, and reducing the likelihood of disputes by negotiating buy-sell agreements. We work together with our Business, Investment, and Transactional Tax group and with our client’s other advisers to advise business owners at all stages.

Pre-Immigration and U.S. Tax Planning for Foreign Individuals

Today’s families often span continents and borders. Caplin & Drysdale attorneys have extensive experience advising U.S. nonresident noncitizens on efficient structuring of investments into the U.S., often utilizing corporate entities or trusts, to minimize U.S. estate and income tax exposure. We also advise clients on restructuring their assets prior to a move to the U.S. to minimize future income and estate tax exposure, utilizing strategies including pre-immigration transfers and trusts, recognizing gain, and disposing of assets that create tax inefficiencies. Our team is experienced in analyzing the U.S. tax impacts of foreign trusts, foundations, Stiftungen, usufructs, and other structures, as well as advising regarding the domestication of such arrangements. We not only advise on and implement such plans, but also guide clients step-by-step through the associated reporting and compliance requirements. The Private Client Group draws on the knowledge of our International Tax colleagues as well as a broad network of advisers in other countries to offer comprehensive advice on cross-border issues.


U.S. citizens who relinquish their citizenship or long-term residents who cease to be lawful permanent residents are deemed to have expatriated for U.S. federal income tax purposes. Unless an exception applies to a specific expatriate or to a specific asset owned by an expatriate, such individuals are treated as having sold all of their assets on the day before expatriation. Moreover, special rules apply to gifts and bequests made by certain expatriates to U.S. beneficiaries. The exceptions to these rules can depend upon or interact with other provisions of the Code or U.S. tax treaties. Caplin & Drysdale attorneys have extensive experience in advising potential expatriates on the application of these rules and their exceptions.

Philanthropic and Planned Giving

Working together with our colleagues in the Exempt Organizations practice, we are uniquely positioned to advise high-net-worth individuals on charitable planning strategies. Whether the client wishes to give during life or at death, we can advise on the most appropriate structure for carrying out the client’s objectives. Caplin & Drysdale attorneys have extensive experience creating private foundations, facilitating gifts through donor advised funds or community foundations, incorporating LLCs for charitable giving, and establishing wholly-charitable and split-interest trusts. We are also well versed on the tax issues regarding giving through 501(c)(4) organizations, as well as the tax and governance issues faced by private foundations. We enjoy assisting clients in realizing their charitable legacies.

Ruling Requests on Income, Estate, Gift, and GST Tax Issues

In some circumstances, before undertaking a transaction it is advisable to get the views of the IRS National Office. Building on years of government service and experience, Caplin & Drysdale attorneys frequently represent clients seeking rulings from the IRS. Most frequently the subject matter is related to the generation-skipping transfer tax, typically seeking assurances that modifications to an exempt trust will not alter the trust’s inclusion ratio, or seeking leave to make a late retroactive election to apply GST exemption or opt into or out of automatic allocation of GST exemption. We often seek gift, estate, and income tax rulings in these matters as well. We have leveraged our extensive experience getting so-called “9100 relief” for missed GST elections, and used that process to successfully obtain permission to make late QTIP elections, portability elections, section 754 elections, and various late elections related to S corporations. 

Audit, Appeals, and Litigation of Income, Estate, and Gift Tax Matters

Caplin & Drysdale attorneys are regularly called upon to advise clients with respect to complex and large-value estate and gift tax controversies, as well as income tax issues for individuals, trusts, and estates. Often it is to the client’s advantage to resolve issues with the IRS as early as possible, prior to litigation. We are adept at negotiating advantageous settlements at both the exam and IRS appeals levels. Should litigation become necessary, we assemble an integrated team including Caplin & Drysdale’s experienced Tax Disputes attorneys. Representative matters include:

  • Defending estate and gift tax valuations of hard-to-value assets such as closely held businesses and artwork;
  • Representing international athletes and entertainers with respect to income tax audits of endorsement income;
  • Litigating in Tax Court with respect to the availability of an estate tax charitable deduction arising from the disposition of a “decanted” trust;
  • Representing non-U.S. citizens before the IRS Office of Appeals regarding income tax residency, including application of complex technical claims relating to use of the "closer connection" exception; and
  • Advising clients in the audit, appeal, and litigation of gift and estate tax controversies regarding the income, gift, and estate tax treatment of irrevocable trusts.

Expert Witness on Tax and Trust Issues

Because of our deep knowledge and experience across a wide range of subjects, members of the Private Client group are often hired as expert witnesses on tax, estate planning, and trust matters. Our expertise runs the gamut from domestic and cross-border matters involving different inheritance regimes to estate, gift, and generation-skipping transfer tax and associated areas of income tax and closely-held business planning.

Foreign Account Reporting

As discussed in more detail with respect to our Tax Disputes practice, Caplin & Drysdale attorneys have extensive experience advising clients on the reporting of foreign accounts. We have assisted more than 1,000 clients through the voluntary disclosure process. We have also advised foreign financial institutions on compliance issues.


Caplin & Drysdale attorneys assist with the probate and revocable trust administration of current clients. We also work on select probate matters for new clients presenting complex and interesting issues, such as estates that would benefit from postmortem planning, probate involving foreign Wills or foreign assets, administration of estates including unreported foreign assets, and the establishment and funding of charitable organizations that will inherit the residue of an estate. 

  • Anne J. O'Brien
  • Alison F. Egan
  • Jonathan S. Brenner
  • Kirsten Burmester
  • Leila D. Carney
  • Darshan Chulani
  • William D. Fournier
  • Victor A. Jaramillo
  • Irene E. Kwon
  • James E. Salles
  • Stafford Smiley
    Senior Counsel

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