Doug is the leader of Sullivan's International Tax Practice Group. He concentrates his practice on international tax planning for clients in a wide range of industries with a particular emphasis on U.S.-based clients investing in foreign jurisdictions. Additionally, Doug works with Sullivan’s Fintech & Blockchain Group, advising clients on the tax implications of multi-jurisdictional cryptocurrency and fintech-related ventures.

Doug is a former co-chair of the International Tax Committee of the Boston Bar Association, a member of the Board of Advisors for Practical U.S./International Tax Strategies, a contributing author for Lexis Practice Advisor and a member of the adjunct tax faculty at Boston University School of Law. Doug is also a frequent speaker at various conferences and webinars on international tax topics for Bloomberg Tax, Financial Executives International, Boston Bar Association and the International Fiscal Association.

Representative Client Work

  • Restructured numerous foreign and domestic businesses in response to the enactment of the 2017 Tax Cuts and Jobs Act
  • Structured numerous tax efficient multi-jurisdictional mergers, acquisitions, dispositions and reorganizations for public and private clients in the financial services, life sciences, manufacturing, private equity, technology and venture capital industries
  • Designed cross-border financing strategies, including hybrid debt structures, for multiple domestic and foreign acquisitions and restructurings and assisted clients in the recapitalization of foreign operations to reduce foreign tax burdens and enhance foreign earnings repatriation efficiency
  • Advised clients on capital loss planning, foreign tax credit utilization, foreign holding company structures, treasury and cash flow management, transfer pricing and migration of intellectual property to tax-favored jurisdictions
  • Represented a Hong Kong-based fabric manufacturer with a presence in 8 countries and 3 continents in migrating its global research and development centre by assisting the company with strategy design and implementation of the project, including acting as lead counsel for a worldwide legal team in Hong Kong, the BVI, the United Kingdom, Mauritius, Cyprus, Indonesia and Singapore
  • Provided U.S. tax advice to an Israel-based public company on its $117 million reverse IPO
  • Led a worldwide team of attorneys and other advisors to restructure foreign operations in 20 countries for a $2 billion public manufacturing company
  • Served as lead counsel for a 10-country reorganization of a public manufacturing company
  • Advised U.S. and non-U.S. clients on structuring cross-border real estate investments ranging from $10 million to $2 billion
  • Represented public and private clients in matters before the U.S. Internal Revenue Service, including controversies, voluntary disclosures related to offshore activities and private letter rulings  
  • Counseled nonresident families on pre-immigration U.S. tax and estate and gift planning matters, including advising a foreign individual who established a foreign trust with U.S. and non-U.S. beneficiaries that required coordinating the complex multijurisdictional rules to satisfy the client’s personal objectives of preserving wealth and passing her assets to her children while, at the same time, meeting the numerous tax and legal requirements of the countries involved; and assisting a U.S. citizen regarding her inheritance of substantial foreign assets to ensure she received such assets without any adverse US estate, gift or income tax consequences while ensuring there are no adverse consequences for the nonresidents in their respective foreign countries

Bar & Court Admissions

  • Massachusetts
  • U.S. District Court, District of Massachusetts
  • U.S. Tax Court

Education

  • LL.M., Taxation, University of Miami School of Law
  • J.D., cum laude, University of Miami School of Law; Projects Editor, Miami Law Review
  • B.A., cum laude, Harvard University

Community Engagement

  • Lecturer in Law, Boston University School of Law, Graduate Tax Program
  • Co-Chair, International Tax Committee, Boston Bar Association, 2009-2011
  • Advisory Board, Practical U.S./International Tax Strategies
  • International Fiscal Association
  • Taxation and International Law Sections, American Bar Association

Languages

  • Spanish

Awards & Honors

  • Boston Magazine 2021 Top Lawyers, Tax (2021)
  • Chambers USA, Tax (Massachusetts) (2017-2019)
  • The Legal 500 U.S., International Tax (2014-2022)
  • The Legal 500 U.S, Fintech (2021-2023)
  • Best Lawyers in America® (2011-2023)
  • Massachusetts Super Lawyers (2013, 2016-2022)
  • Tax Controversy Leaders' Guide, International Tax Review (2011-2014, 2016-2023)
  • "Rising Star," Massachusetts Super Lawyers (2009-2012)

Seminars & Presentations

Practices

Industries

Jump to Page