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.
Awards & Rankings
•Super Lawyers, Washington, D.C., 2016-2017
•Best Lawyers in America, Leading Lawyer, 2013; Listed 2013-Present
•Martindale-Hubbell AV Preeminent
•Caplin & Drysdale Improves Ranking in 2019 Best Lawyers in America, August 15, 2018
•Stafford Smiley Comments on Changes to the Estate Tax in the House Tax Bill, Tax Notes, November 20, 2017
•Caplin & Drysdale Earns Top Ranking in 2018 Best Lawyers in America, August 15, 2017
•Caplin & Drysdale Lawyers Listed Among D.C.'s Most Prominent Practitioners, Super Lawyers, April 27, 2017
•Best Lawyers in America Lists 18 Caplin & Drysdale Attorneys, U.S. News & World Report, August 15, 2016
•Super Lawyers Recognizes Caplin & Drysdale Lawyers from Several Practice Areas, Super Lawyers, April 26, 2016
•Caplin & Drysdale Lawyers Earn Best Lawyers Ranking, August 21, 2014
•19 Caplin & Drysdale Attorneys Achieve Best Lawyers in America Ranking, U.S. News & World Report, October 21, 2013
Recent Speaking Engagements
•Faculty, Tax Planning in the U.S., WU/Institute for Austrian and International Tax Law and Akademie der Wirtschaftstreuhander GmbH, LL.M. Program in International Tax Law, March 20, 2015
•Speaker, Tax Reform in the United States, Moscow State Law Academy, October 25, 2013
•Speaker, Tax Reform in the United States, International Fiscal Association, Russian Branch, October 23, 2013
•Speaker, Advance Pricing Agreements in U.S. Tax Practice, Moscow State Law Academy, 2nd Annual Conference, October 17, 2013
•Speaker, Avoidance of Double Taxation and the Prevention of Fiscal Evasion, American Chamber of Commerce, Tax & Financial Services Committee Meeting, September 20, 2013
•Speaker, The Foreign Account Tax Compliance Act (FATCA), International Fiscal Association, Russian Branch, October 11, 2011
• Paradise Papers: U.S. Citizens and Residents Required to Report on Offshore Assets, with Mark D. Allison, J. Clark Armitage, Peter A. Barnes, and Arielle M. Borsos, Caplin & Drysdale Client Alert, November 6, 2017
• The Final OECD BEPS Tome Has Arrived, with H. David Rosenbloom, Patricia Gimbel Lewis, J. Clark Armitage, and Peter A. Barnes, Caplin & Drysdale Client Alert, October 8, 2015
• Me, Myself, and My Subsidiary: A Shift in the Intent Standard in Related-Party Hybrid Debt Cases, with Victor A. Jaramillo, Corporate Taxation, September 1, 2013
• Amazon.com v. Commissioner: Veritas Redux?, with Neal M. Kochman, Corporate Taxation, August 1, 2013
• Cruising Toward Safe Harbors for Transfer Pricing?, with Patricia Gimbel Lewis, Corporate Taxation, March 1, 2013
• Mutual Administrative Assistance in Tax Matters, Journal of Corporate Taxation, March 1, 2013
• U.K. Excess Profits Tax Under U.S. Foreign Tax Credit, Corporate Taxation, January 1, 2013
• Recent Developments: U.K. Excess Profits Tax Under the U.S. Foreign Tax Credit, Corporate Taxation, January 1, 2013
• Foreign Tax Credit Generators, Corporate Taxation, May 1, 2012
• Case Updates-Dell Products (Norway) General Electric Capital (Canada) SNF (Australia), with Victor A. Jaramillo, Corporate Taxation, March 1, 2012
• Commissionaire and Contract Manufacturing Arrangements - New Developments on Permanent Establishment Issue, Corporate Taxation, January 1, 2012
• Taxation of Passive Foreign Investment Companies: Current Rules, Problems and Possible Solutions, Corporate Taxation, November 1, 2011
• 2010 Treaty Developments, Corporate Taxation, November 1, 2011
• Qualified Intermediaries, The EU Savings Directive, Trace--What Does FATCA Really Add, Corporate Taxation, September 1, 2011
• India's Proposed Direct Taxes Code - Highlights For Corporate Taxpayers, Corporate Taxation, July 1, 2011
• ITPF - Georgetown University Law Center Conference on Reform of International Tax, Corporate Taxation, May 1, 2011
• Putting an End to Foreign Tax Credit 'Splitting' Transactions, Corporate Taxation, March 1, 2011
• President Obama's Efforts at International Tax Reform, Corporate Taxation, January 1, 2011
• A Shift Toward Consumption Taxes: The Tax Policy Prescription For The Fiscal Ills of The Global Financial Crisis, Corporate Taxation, July 1, 2010
• Loan Guarantees and Transfer Pricing, Corporate Taxation, May 1, 2010
• National Westminster Bank: Will the IRS Ever Give Up, Corporate Taxation, March 1, 2010
• The Curious Case of The Partial Loophole Closer, Corporate Taxation, January 1, 2010
• 2009 Treaty Developments, with Kirsten Burmester, Corporate Taxation, November 1, 2009
• The Practical Impact of FIN48 - Is it Moving Abroad?, November 1, 2007
Other Professional Affiliations
Member, American Bar Association
Member, International Fiscal Association
Member, U.S. Council for International Business
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.
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