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Angelo Gentile

Partner Admitted to the Ontario Bar: 2007

Angelo is a member of the firm’s Tax Group. His practice focuses on tax litigation and commodity taxation, including goods and services tax and harmonized sales tax (GST/HST), provincial sales tax (PST), land transfer tax, employer health tax, tobacco tax and gasoline tax. Angelo has experience in resolving disputes arising under the Income Tax Act, the Excise Tax Act, the Customs Act, the Excise Act, the Excise Act, 2001, the Ontario Retail Sales Tax Act, the Canada Pension Plan and the Employment Insurance Act.

Angelo excels at understanding and communicating the complex technicalities of tax law. His deep knowledge and personable approach allow him to resolve his clients’ tax issues and disputes on an expedited basis, particularly when negotiating with the Department of Justice and the Canada Revenue Agency. His open and honest communication quickly instills in his clients a confidence that he is looking out for their best interests.

He has been successful in resolving a wide range of tax disputes at early stages of the process. Particularly in the field of sales tax, Angelo’s in-depth knowledge of GST/HST and PST, coupled with his practical knowledge of the tax litigation process and the CRA administrative decision-making process, allows him to arrive at creative solutions to sales tax disputes that would have otherwise proceeded to trial. However, if a dispute cannot be resolved before trial, Angelo has experience representing clients before the Tax Court of Canada, the Federal Court, the Federal Court of Appeal and the Superior Court of Justice. Angelo also represents clients in making voluntary disclosures with the CRA and the Ontario Ministry of Finance.

Angelo advises Canadian and non-resident clients across a variety of industries, including real estate, retail, natural resources, financial services, health care, energy, communications, technology, and manufacturing. In addition, Angelo advises clients in the charitable and not-for-profit sector.

Awards & Recognition

  • Recognized by International Tax Review as an Indirect Tax Leader.
  • Recipient of the 2016 Normand Guérin Award for his outstanding contribution to the study of commodity taxation.

Professional Involvement


  • Canadian Bar Association
  • Canadian Tax Foundation
  • Law Society of Ontario
  • Ontario Bar Association

Community Involvement

  • Advisor/Mentor, Pro Bono Students Canada/Tax Court of Canada Pro Bono Project

Representative Matters

Counsel to Mr. Bozzer in Bozzer v. The Queen, 2011 FCA 186.

Counsel to Heritage Education Funds Inc. in Heritage Education Funds Inc. v. Her Majesty the Queen, 2010 TCC 161.

Advising a confidential client on a settlement in a GST/HST tax court appeal, in respect of an assessment of a financial institution's input tax credit allocation methodology.

Advising a confidential client on the CRA Appeals Division to vacate a C$1.3 million GST/HST assessment within five months of the date of assessment.

Advising a confidential client on the CRA Appeals Division to vacate a C$4 million CPP/El assessment.

Advising a confidential client on a settlement in a GST/HST tax court appeal, in respect of the application of a penalty under the Excise Tax Act.

Advising a confidential client on a settlement of a director’s liability assessment prior to a tax court hearing.

Advising a confidential client adverse to the Department of Justice/CRA to vacate an assessment of a GST/HST New Housing Rebate prior to a tax court hearing.

Advising a confidential client on numerous GST/HST voluntary disclosures made by businesses and registered charities.

Selected Speaking Engagements

Presenter, "The Québec Runaway Bride: Reflections on the Canadian Indirect Tax Harmonization Process," Chartered Professional Accountants Commodity Tax Symposium, October 25, 2016

Presenter, "Protecting Sensitive Tax Data & Nuances of Tax Litigation," The Institute of Law Clerks of Ontario, Just For Law, 26th Annual Conference, May 13, 2016

Presenter, "Commodity Tax – Case Law Update," Tax Executives' Institute 50th Annual Canadian Tax Conference, May 3, 2016

Presenter, "Unsuspecting Applications of the Fair Market Value Rule: Defending Challenges on Audit," Chartered Professional Accountants, September 29, 2015

Presenter, "Directors' Liability for Unremitted Corporate Taxes: What Every Director Needs to Know," Continuing Professional Development Bootcamp, Toronto, November 12, 2014

Presenter, "Tax and Privilege: A Primer," Continuing Professional Development Bootcamp, Toronto, November 30, 2011

Presenter, "Case Law Update: While You Were Away This Summer," Ontario Bar Association Tax Law Section, September 21, 2011

Presenter, "Case Law Update: A Fast and Furious Survey of Recent Decisions," Ontario Bar Association Tax Law Section, April 14, 2011

Presenter, Canadian Tax Foundation Young Practitioners (Toronto), "HST: Key Issues of the Day," January 26, 2011

Presenter, FMC Tax Group's Spring Webinar, May 14, 2008

Selected Publications

Co-Author, "Case Law Update," 2012 CPA Commodity Tax Symposium, September 2012

"Bozzer: An Interest-ing Victory for All Canadian Taxpayers," Tax Topics, August 2011

"Husky Oil Limited v. The Queen: Clarifying the Scope of the Amalgamation Anti-Avoidance Rule," Tax Litigation Journal, Federated Press, Volume XVII, No. 3, 2010

Contributor, Canadian Transfer Pricing, CCH Canadian Limited, 2nd Edition

Co-Author, "New Litigation Process Conference Rules in Tax Court Proceedings," Tax Litigation Journal, Federated Press, Volume XVI, No. 4, 2010

Co-Author, "Trends in Sales Tax Litigation," Report on the 2008 Canadian Tax Foundation Conference, 2009

Co-Author, "GST and Commodity Tax Issues in Cross-Border Transactions: Expecting the Unexpected," Report on the 2007 Canadian Tax Foundation Conference, 2008

Contributing Writer, "Federal Tax Practice," CCH Canadian Limited

Co-Author, "Limit the Uncertainty" (regarding the scope of limitation periods in tax assessments), CA Magazine, April 2006

Contributing Writer, "Charities, Non-Profits and Philanthropy Under the Income Tax Act," CCH Canadian Limited, 2006


Publications Article Feb 27, 2018 Highlights of the 2018 Federal Budget
Publications Article Nov 17, 2017 Cannabis Excise Duties
Publications Article Sep 12, 2017 General Partner Distributions: Subject to GST/HST?


  • LLM, University of California, Berkeley, School of Law, 2014
  • JD (Honours), University of Toronto, 2006
  • B.A.Sc. Industrial Engineering (Hons), University of Toronto, 2003