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Caplin & Drysdale is known for sophisticated tax planning strategies. The firm’s well-regarded group of trusts and estates attorneys [are] strong on complex 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. View our brochure.

Practice Area(s)

  • Domestic Planning Work
  • Domestic Controversy Work
  • International Planning Work
  • International Controversy Work

Domestic Planning Work

Caplin & Drysdale attorneys assist U.S. clients with their estate plans, always with an eye toward wealth preservation through tax efficiency. 

Representative Engagements

GRAT Planning:
 Caplin & Drysdale attorneys set up a GRAT to which mineral interests were contributed. The primary issue was the valuation of the property interests, which had not yet been explored and were subject to litigation. Caplin & Drysdale attorneys planned the transaction, then managed the appraisal process and the presentation of the issue on the gift tax return. 

Satisfying Charitable Objectives: Client owned a unique collection of assets. Client came to Caplin & Drysdale wanting to establish a museum to house his unique collection of assets upon his death. The collection would require specialized care. Working with attorneys in our exempt organization's practice, we provided for the creation of a private foundation under Client's will, to be established after Client's death by his personal representative. On behalf of the foundation, Caplin & Drysdale later negotiated for an established charitable organization to take possession of the collection, with detailed specifications as to the care to be provided. The collection is now accessible by the public. The private foundation continues to operate, advancing the charitable causes that were dear to the client. 

Domestic Controversy Work

Caplin & Drysdale attorneys are frequently called upon to assist with complex estate and gift tax examinations, as well as income tax issues for individuals, trusts and estates. We also frequently represent clients' interests before the National Office of the IRS on requests for private letter rulings.

Representative Engagements

Defending a trust's income tax position: Caplin & Drysdale attorneys were retained to consider a planned trust division and recommend a tax position designed to maximize the possibility of obtaining a charitable contribution deduction upon the termination of family trusts. The amount at issue is about $250 million in tax.  The family is following Caplin & Drysdale's advice by taking the initial position on a claim for refund, to be followed by a refund suit, if necessary.   

Private Letter Ruling: Caplin & Drysdale attorneys obtained a favorable private letter ruling from the IRS affirming that there are no adverse tax consequences to a settlement agreement entered into by the trust beneficiaries and approved by the state court. The settlement agreement resolved an 80-year old dispute amongst the beneficiaries, who were represented by 15 separate law firms. A committee of those attorneys selected Caplin & Drysdale to represent them before the IRS. 

International Planning Work

Caplin & Drysdale attorneys assist foreign and domestic clients with cross-border income and estate planning with the ability to address complex tax issues ranging from the application of tax treaties to issues related to interests in foreign companies (CFCs/PFICs) and trusts, and from relocation of families to the United States to expatriation from the United States. 

Representative Engagements

Bringing a Foreign Inheritance Into the United States: Caplin & Drysdale attorneys assisted U.S. clients with tax structuring and reporting of receipt of a large ($100 million) bequest from a foreign estate, involving several complex foreign trusts and closely-held investment and operating companies. We minimized potential PFIC and trust "throwback" issues. Planning involved exchange of privately-held investment companies for shares of a publicly-listed foreign investment company and decanting of trust assets into new U.S. domestic trusts, requiring meshing of foreign and U.S. tax and legal principles. 

Trust Migration: Caplin & Drysdale attorneys assisted a U.S. client with tax structuring and reporting of migration of $11 million foreign-administered NY law trust holding foreign operating companies through a BVI investment company. Planning involved forensic reconstruction of company history and "check-the-box" liquidation of the investment company to avoid possible PFIC and/or CFC taint.

Working with Stars: Caplin & Drysdale attorneys assisted high-profile foreign athletes and entertainers in determining their U.S. tax positions and in developing strategies to minimize tax burden while maximizing profits through tax efficiency.

International Controversy Work

Caplin & Drysdale attorneys assist foreign clients with U.S. tax examinations and other interactions with the Internal Revenue Service. 

Representative Engagements

Audit of an International Athlete: Caplin & Drysdale attorneys assisted with the U.S. tax examination of foreign athlete's attributable U.S. source endorsement income, requiring submission of a protest and a competent authority request to avoid double taxation of income previously taxed at the corporate level in the foreign country of the athlete's residence. The client saved nearly $2.0 million in tax as a result of this work.

Income Tax Examination of an Expatriate: Caplin & Drysdale attorneys assisted a former U.S. citizen with a protest of an IRS income tax examination determination that the client exceeded U.S. residence test, requiring complex technical claims relating to use of the "closer connection" exception. Over $75 million in tax and penalties was at issue.