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Practice Area(s)


  • J.D., Harvard Law School, 1976, magna cum laude
  • B.A., Yale University, 1970, summa cum laude, Phi Beta Kappa

Bar and Court Admissions

  • New York
  • District of Columbia
  • U.S. Court of Appeals, Federal Circuit
  • U.S. Court of Federal Claims
  • U.S. Supreme Court
  • U.S. Tax Court
  • District of Columbia Court of Appeals

Other Professional Affiliations

Member, American Bar Association

Member, International Fiscal Association

Member, U.S. Council for International Business

Stafford Smiley

Senior Counsel, Washington, D.C.
(202) 862-5093 | v-card | PDF

Stafford Smiley is a Senior Counsel in Caplin & Drysdale's Washington, D.C., office and a Professor in the Graduate Tax LL.M. Program at Georgetown University Law Center.

Mr. Smiley began his legal career as a law clerk to Judge Arnold Raum of the United States Tax Court. He joined Caplin & Drysdale in September 1978 and became a Member of the firm in January 1983.

Mr. Smiley is fluent in French and Russian.


Mr. Smiley's practice focuses on the taxation of partnerships, S corporations, and other pass-thru entities. He also works generally on business taxation issues and issues relating to the ownership and transfer of assets for tax purposes. Mr. Smiley has extensive experience as tax counsel in international financing, leveraged lease, and other transactional settings. 

He represents a number of large family-held businesses, for whom he provides not only business tax advice, but also general business, trust, estate, and gift advice.

Mr. Smiley also represents a number of international finance organizations, for whom he does international tax planning work, primarily in the areas of international structured finance and transfer pricing matters, including advanced pricing agreements in particular. 

Professional Activities

Mr. Smiley has taught in the Graduate Tax Program at Georgetown University Law Center as an Adjunct Professor since 1996.  He became a Visiting Professor in 2008 and a Professor in 2010. In the Spring of 2012, Mr. Smiley began teaching a course on Income Tax Accounting. Prior to teaching at Georgetown, he was an Adjunct Professor at the George Washington University Law Center. Mr. Smiley has lectured at the New York University Annual Institute on Federal Taxation, the University of Virginia Law School, and other tax-oriented educational institutions. He holds a Professorship at the University of Lodz (Poland) and teaches and lectures extensively in tax programs at universities abroad. Furthermore, Mr. Smiley has lectured on the "Basics of U.S. Tax Audit and Tax Litigation" at  Caspian "Social" University in Almaty, Kazakhstan, and instructed a two-week master class on "U.S. International Tax" in the Public Finance Masters program at Moscow State Institute of International Relations (MGIMO).

Mr. Smiley served for many years as the International Developments Editor for the Journal on Partnership Taxation, and now serves as International Developments Editor for Corporate Taxation. In 2006, Mr. Smiley became the Examiner in U.S. Tax Law for the Chartered Institute of Accounts in the United Kingdom.

Awards & Rankings

  • Super Lawyers, Washington, D.C., 2016-2017
  • Best Lawyers in America, Leading Lawyer, 2013; Listed 2013-Present
  • Martindale-Hubbell® AV® Preeminent™

Speaking Engagements

Click here for a full list of speaking engagements.

Recent Publications

Click here for a full list of publications.