Stafford Smiley
Caplin & Drysdale
Stafford Smiley Senior Counsel

P: (202) 862-5093

F: (202) 429-3301

Washington, D.C. Office


Stafford Smiley is a Senior Counsel in Caplin & Drysdale's Washington, D.C., office and a Professor and the Faculty Director 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.

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 2007 and a Professor in 2008. 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.

Mr. Smiley served for many years as the International Developments Editor for the Journal on Partnership Taxation, and more recently served as International Developments Editor for Corporate Taxation. From 2006 through 2016, Mr. Smiley served as the Examiner in U.S. Tax Law for the Chartered Institute of Accounts in the United Kingdom.

Practice Area(s)

Awards & Rankings

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

Recent News

Speaking Engagements

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Recent Publications

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  • 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
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