Richard W. Skillman is a Member in Caplin & Drysdale's Washington, D.C., office focusing in federal taxation. Mr. Skillman's practice covers a broad cross-section of domestic and international tax matters and includes the representation of taxpayers in tax controversies as well as tax planning. His practice focus includes insurance companies and products, executive compensation and other employee benefits, corporate tax, tax accounting, and international tax.


Between 1999 and 2002, Mr. Skillman served as Deputy Chief Counsel and Acting Chief Counsel of the Internal Revenue Service. As Acting Chief Counsel, Mr. Skillman was the chief legal official of the IRS. He held final authority for all legal and litigating positions of the IRS and management responsibility for approximately 2500 Chief Counsel employees in more than 50 offices nationwide.

Mr. Skillman is a member of the Tax Sections of the ABA and of the D.C. Bar. He formerly taught Corporate Tax as an Adjunct Professor of Law at Georgetown University Law Center and has lectured and written articles on a broad range of tax subjects.

Mr. Skillman holds a B.A. from Amherst College and a J.D. from New York University Law School, where he graduated first in his class and served as Editor-in-Chief of the N.Y.U. Law Review. After law school, he served as law clerk to Judge Gibbons of the U.S. Court of Appeals for the Third Circuit and to Chief Justice Burger of the U.S. Supreme Court. 

Admissions & Education

Bar & Court Admissions
  • New York
  • District of Columbia
  • District of Columbia Court of Appeals
  • Supreme Court of New York
  • U.S. Court of Appeals, Seventh Circuit
  • U.S. Supreme Court
  • U.S. Tax Court

J.D., New York University School of Law, 1970, cum laude; Order of the Coif; Editor-in-Chief, N.Y.U. Law Review

B.A., Amherst College, 1967, cum laude

Recognitions & Noteworthy

Honors & Recognitions
  • Chambers USA, 2010-2017
  • The Legal 500, Leading Lawyer, 2010-2013; Recommended 2014-2020, 2024
  • The Legal 500, International Tax Team of the Year, 2014-2015
  • Best Lawyers in America, Lawyer of the Year, 2014 and 2021; Listed 1995-Present
  • Super Lawyers, Washington, D.C., 2008-Present
  • The Washingtonian, Top Lawyer, 2009, 2011-2012, and 2015; Lifetime Achievement Lawyer, 2022
  • Fortune Magazine, Top Rated Lawyers in Labor and Employment, 2014
  • Expert Guides' World's Leading Tax Advisers, 2014
  • Martindale-Hubbell® AV® Preeminent™

Government Service

Acting Chief Counsel, Internal Revenue Service, Office of Chief Counsel, 2001-2002

Deputy Chief Counsel, Internal Revenue Service, Office of Chief Counsel, 1999-2002

Law Clerk, Honorable Warren E. Burger, U.S. Supreme Court, 1971-1972

Law Clerk, Honorable John J. Gibbons, U.S. Court of Appeals for the Third Circuit, 1970-1971

Professional Activities & Affiliations

Other Professional Affiliations

Member, American Bar Association, Section of Taxation

Member, District of Columbia Bar, Tax Committee

Newsroom & Publications

Speaking Engagements
  • Richard Skillman to Speak on Administrative Procedure Act at 6th Annual Global Transfer Pricing Conference
  • Richard Skillman to Speak on Ponzi Scheme Panel
  • Richard Skillman to Speak on Executive Compensation
Publications & Alerts
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