Caplin & Drysdale, Chartered > Washington DC, United States > Firm Profile

Caplin & Drysdale, Chartered
United States

Tax > US taxes: contentious Tier 2

Caplin & Drysdale, Chartered is a Washington DC-based boutique known for its strength in both civil and criminal tax disputes that is hailed by clients as ‘true leaders of the tax litigation bar’. The group acts on behalf of both businesses and private individuals and is noted for its strength in matters involving undisclosed offshore bank accounts and assets, though it also routinely handles other complex international tax mandates. Leading the team are highly experienced criminal tax practitioner Scott Michel and Christopher Rizek, whose practice covers conservation easements, estate and gift taxes, and tax shelter investigations. Michel and Rizek are praised for being ‘knowledgeable, accessible, and very sensitive in dealing with clients’. Niles Elber handles both civil and criminal matters and has recently demonstrated strengths in the conservation easement space, Mark Matthews is primarily active on behalf of high net worth individuals, including those holding assets internationally, and Charles Ruchelman is a key name for captive insurance matters. Other core team members include international tax specialist Victor Jaramillo as well as Benjamin Eisenstat.

Practice head(s):

Scott Michel; Christopher Rizek


‘The entire team is first-rate. Scott Michel, Mark Matthews, and Chris Rizek are as fine as any tax controversy lawyers in the land. Niles Elber and Victor Jaramillo are also formidable. They are all true leaders of the tax litigation bar, not just by their casework, but also by providing their time and talents to issues on behalf of taxpayers in general.’

‘The experience and judgment they provide on cases is profound. I appreciate their ability to evaluate cases and their strategic thinking on how to reach results that exceed expectations.’

‘Scott and Niles are knowledgeable, accessible, and very sensitive in dealing with clients who are vulnerable. They are respected by US tax administrators, which is critical in an area which can result in substantial penalties or incarceration.’

‘Scott and Niles are comforting in files which require a leap of faith.’

Work highlights

Tax > US taxes: non-contentious Tier 6

Caplin & Drysdale, Chartered’s transactional tax has a strong reputation for working closely with the firm’s private client practice to assist individuals and families with wealth structuring and tax and estate planning issues. Jonathan Brenner in New York has long-standing experience advising domestic and overseas businesses, US citizens, expatriates, and foreign nationals on tax structuring. He leads the group alongside Washington DC-based private client specialist Anne O’Brien. DC’s Richard Skillman focuses on federal taxation, while Josiah Child in New York counts sovereign wealth funds, pension funds, and high-net-worth individuals as clients. Elizabeth Stevens in Washington DC advises partnerships, LLCs, and S-corporations. Former practice co-heads Beth Kaufman and Megan Wernke left the firm in May 2023.

Practice head(s):

Jonathan Brenner; Anne O’Brien

Caplin & Drysdale was formed in 1964 by Mortimer M Caplin, who served as Commissioner of the Internal Revenue Service under Presidents Kennedy and Johnson, and Douglas D Drysdale, who taught law for several years at the University of Virginia School of Law. For over half a century, the firm has been a leading provider of tax, tax controversy, and litigation legal services to corporations, individuals, and nonprofits throughout the United States and around the world. Caplin & Drysdale is also privileged to serve as legal advisors to accounting firms, financial institutions, law firms, and other professional services organizations.

The firm’s reputation over the years has earned it the trust and respect of clients, industry peers, and government agencies. Moreover, clients rely on the lawyers’ broad knowledge of the law and keen insights into their business concerns and personal interests. Caplin & Drysdale lawyers’ strong tactical and problem-solving skills — combined with substantial experience handling a variety of complex, high-stakes matters in a boutique environment — make Caplin & Drysdale one of the nation’s most distinctive law firms.

With offices in Washington, D.C., and New York City, Caplin & Drysdale also offers counseling on matters relating to bankruptcy, corporate law, employee benefits, exempt organizations, political activity, private client services, and white-collar defense.

Main areas of practice: Bankruptcy: for over 30 years the firm has protected the rights of creditors in courts throughout the US. The firm is regularly retained in Chapter 11 bankruptcy cases to analyze and resolve high-profile, complex and cutting-edge disputes. The practice encompasses the full range of issues affecting creditors in bankruptcy proceedings.

Business investment and transactional tax: the firm has broad experience advising and representing public companies, other business entities, and their principals in tax planning and controversy matters. Such business entities include domestic and foreign financial institutions, manufacturing companies, insurance companies, and hedge fund managers. The firm’s substantive tax experience includes corporate tax, partnership tax, subchapter S, taxation of regulated investment companies and real estate investment trusts, and taxation of insurance companies and products.

Complex litigation: the firm’s litigators are regularly asked to handle complex business, financial, and commercial disputes that have put a business in peril, and represent plaintiffs worldwide seeking to have their rights vindicated through the court system. The group efficiently handles matters of varying sizes, emphasizing close communication with clients, hands-on involvement by senior lawyers, lean staffing, and aims to deliver excellent value for clients.

Corporate law: the firm helps clients choose whether to operate as a partnership, limited liability company, or corporation. The group also incorporates or forms entities and advises on day-to-day business matters.

Employee benefits: the firm advises on design/administration of qualified plans; legislative/regulatory changes; representation before the IRS; Title I of ERISA; executive compensation; health and welfare benefits; tax-exempt and governmental employer representation; financial institution and service provider counseling; and dispute resolution.

Exempt organizations: the rules governing exempt organizations are technical and careful compliance is a necessity. Caplin & Drysdale advises both established exempt organizations and entities seeking tax-exempt status.

International tax: Caplin & Drysdale’s international tax attorneys counsel multinational businesses and US taxpayers with global interests on matters involving IRS rules, transfer pricing and multilateral dispute resolution, etc.

Political activity: the bipartisan political law group provides timely and concise counsel on the high-stakes legal issues that involve ‘pay-to-play’ restrictions, lobbying regulations, campaign finance laws, and ethics rules.

Private client: the firm counsels wealthy individuals on domestic and cross-border tax and estate planning issues, represents clients in IRS disputes and helps individuals with tax compliance issues. The firm is one of few with a focus on expatriation, and attorneys draw upon their vast experience to bring a uniquely informed perspective.

Tax controversies: clients, ranging from multinational corporations to high-net-worth individuals, call upon the firm to advise on a variety of complex tax disputes, including: audits; voluntary disclosures; and criminal enquiries.

President and Member of the firm : Ann C. McMillan (202 862 5080,
General counsel and Member of the firm : James P. Wehner (202 862 5075,