Dashiell Shapiro advises individuals and business entities on a broad range of tax planning and tax controversy matters, federal, state and international. A native of the San Francisco area, he received his undergraduate degree and law degree from the University of Chicago. At the law school, he served as Comment Editor for the University of Chicago Legal Forum.
Prior to joining Wood LLP, Dashiell spent a total of seven years at the U.S. Department of Justice Tax Division litigating tax controversies in federal courts across the country. At the Department of Justice, Dashiell gained extensive experience in all aspects of tax controversy practice in federal district and bankruptcy courts, including trial work and evidentiary hearings, depositions and written discovery, pleadings, motions practice, appeals, and settlements. He regularly handled a docket of 60 to 70 cases, and worked on a variety of matters including tax shelters, statutes of limitation, employment tax disputes, tax liens and collection cases, international tax disputes, summons enforcement in criminal matters, interpretation and defense of Treasury Regulations, and many others. The Department of Justice awarded Dashiell with a Special Commendation Award and an Outstanding Trial Attorney Award.
In between stints at the Department of Justice, Dashiell advised on international tax and financial product taxation in both the accounting firm and law firm settings. He advised hedge funds and investment banks on the taxation of debt and equity products, with a focus on real estate and mortgage-backed securities, and drafted tax opinions. He also published articles in the Journal of Taxation of Investments on exchange-traded notes, withholding tax on cross-border equity swaps under the OECD Model Treaty, and whether FDAP withholding should apply to financial derivatives.
At Wood LLP, Dashiell has successfully represented individuals and companies at all stages of tax controversy, from initial audit inquiries and protests to IRS Appeals, Tax Court, Federal District Court, and Federal Appellate Courts. He has obtained favorable outcomes for taxpayers in a variety of settings, including no-change audit determinations, transitional relief acceptance within the Offshore Voluntary Disclosure Program (OVDP), and 100% concessions of tax and penalties in exam and Appeals. In 2014, he appeared before the California State Board of Equalization and obtained, in a split decision, the Board’s full reversal of a $10 million constructive receipt determination made by the Franchise Tax Board. He has also published a number of articles on tax litigation, TEFRA partnership procedure, statutes of limitation, willfulness and offshore accounts, and goodwill allocations in mergers and acquisitions.
Member, State Bar of California, 2015|
Member, Washington D.C. Bar, 2008
Admitted, United States Court of Federal Claims
Admitted, United States Tax Court
Admitted, Seventh Circuit
| University of Chicago Law School, J.D., 2003|
Merit Scholarship Recipient, Comment Editor: University of Chicago Legal Forum
University of Chicago, B.A., Near Eastern Languages and Civilizations, Honors, 2000
Taxation and Regulation in Decentralized Exchanges, Vol. 36, No. 01, Taxation of Investments (Fall 2018), p. 3.|
Cryptocurrency and the Shifting IRS Enforcement Model, Stanford Journal of Blockchain Law & Policy (June 23, 2018).
How Not to Panic If Coinbase is Turning Over Your Info to the IRS, Cointelegraph (March 5, 2018).
Is Puerto Rico а Crypto Tax Paradise?, Cointelegraph (February 10, 2018).
How Financial Instruments Help to Avoid Big Crypto Tax Bills?, Cointelegraph (February 1, 2018).
Bitcoin Loans and Other Cryptocurrency Tax Problems, Vol. 35, No. 02, Journal of Taxation (Winter 2018), p. 33.
Crypto “Prophets” From 1997 Point to IRS Showdown: Expert Blog, The Cointelegraph (December 8, 2017).
Could Milton Friedman’s “Least Bad Tax” Work for Cryptocurrencies? Expert Blog, The Cointelegraph (November 23, 2017).
Joint Ventures Between Attorneys and Clients, Vol. 26, No. 2, The M&A Tax Report (September 2017), p. 4.
IRS Targets Bitcoin Users, But Is Coinbase the Next UBS?, Vol. 154, No. 13, Tax Notes (March 27, 2017), p. 129.
War On Alternative Currencies Heating Up, with Robert W. Wood, Los Angeles Daily Journal (December 6, 2016), p. 8. Simultaneously published in San Francisco Daily Journal (December 6, 2016), p. 8.
Can Taxpayers Rely on IRS Form Instructions, Vol. 149, No. 7, Tax Notes (November 16, 2015), p. 945.
A Smidgen of Willfulness, with Robert W. Wood, Vol. 23, No. 6, The M&A Tax Report (January 2015), p.5.
IRS Backs Itself Into a Corner in Goodwill Allocations, Vol. 23, No. 6, The M&A Tax Report (January 2015), p. 1.
Lavish Spending and Other ‘Non-Willful’ Acts With Taxes and FBARs, with Robert W. Wood, Vol. 145, No. 8, Tax Notes (November 24, 2014), p. 955.
Tax Payments and Statute Waivers Voided by Duress, with Robert W. Wood, Vol. 142, No. 6, Tax Notes (February 10, 2014), p. 671.
Tax Treaties, International Transactions and Beneficial Ownership (Part II), Vol. 22, No. 6, The M&A Tax Report (January 2014), p. 5.
Tax Treaties, International Transactions and Beneficial Ownership (Part I), Vol. 22, No. 5, The M&A Tax Report (December 2013), p. 1.
Blowing the Whistle on Taxing Whistleblower Recoveries, with Robert W. Wood, Vol. 141, No. 9, Tax Notes (December 2, 2013), p. 983.
Fifty Shades of Grey: Informal Discovery in Tax Litigation, with Robert W. Wood, Vol. 141, No. 3, Tax Notes (October 21, 2013), p. 325.
For Whom the Statute Tolls, with Robert W. Wood, Vol. 140, No. 10, Tax Notes (September 2, 2013), p. 1035.
IRS Takes Odd Stance on Entity Liquidations, with Robert W. Wood, Vol. 22, No. 1, The M&A Tax Report (August 2013), p. 1.
When the IRS Says a Liquidation Is Not a Liquidation, with Robert W. Wood, Vol. 140, No. 5, Tax Notes (July 29, 2013), p. 495.
M&A, Partnerships and Procedures, with Robert W. Wood, Vol. 21, No. 12, The M&A Tax Report (July 2013), p. 5.
Who Controls Goodwill?, with Robert W. Wood, Vol. 21, No. 12, The M&A Tax Report (July 2013), p. 1.
Courts Disagree When It Comes To Tolling Tax Statute, with Robert W. Wood, Los Angeles Daily Journal (June 20, 2013), p. 4. Simultaneously published in San Francisco Daily Journal (June 20, 2013), p. 4.
Munro Stipulations: TEFRA Timing Mismatches Remain, with Robert W. Wood, Vol. 139, No. 12, Tax Notes (June 17, 2013), p. 1433.
FDAP Withholding on Derivatives? A Comparative Perspective, 29 J. Tax'n of Investments 1 (2011).
OECD Treaties: Who Beneficially Owns Dividends in a Total Return Swap?, 27 J. Tax'n of Investments 1 (2009).
Taxation of Exchange-Traded Notes, with D. Mulcahy, 25 J. Tax'n of Investments 3 (2008).
CERCLA § 107 Violates Equal Protection, 2002 U. Chi. Legal F. 331 (2002).