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Angelo Gentile

Angelo Gentile

Partner Admitted to the Ontario Bar: 2007
People > Angelo Gentile

Angelo is Co-Practice Group Leader of the firm’s Tax Group and a member of the Tax Controversy/Tax Litigation Group. His practice focuses on tax litigation and commodity tax, including goods and services tax/harmonized sales tax (GST/HST) and provincial sales taxes. Angelo has extensive experience in resolving tax disputes involving GST/HST, income tax, CPP/EI, excise taxes, Ontario land transfer tax, Ontario employer health tax and Ontario tobacco tax.

Angelo is a natural problem solver. 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 GST/HST, Angelo’s in-depth knowledge of the legislation, 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 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, financial services, retail, natural resources, health care, energy, communications, technology and manufacturing. In addition, Angelo advises clients in the charitable and not-for-profit sector.

Awards & Recognition

  • Recognized in The Canadian Legal Lexpert Directory in the areas of Litigation - Corporate Tax and Commodity Tax/Customs.
  • Consistently 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.
  • Recognized in The Best Lawyers in Canada in the field of Tax Law

Professional Involvement

Memberships

  • 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 Allied Properties Real Estate Investment Trust, a leading operator of distinctive urban workspace in Canada’s major cities and network-dense urban data centres in Toronto, in its acquisition of six urban office properties from Choice Properties Real Estate Investment Trust for $794 million.

Counsel to a confidential financial services client in a GST/HST Tax Court appeal settled in March 2022, in respect of an assessment of tax on services that were subsequently agreed to be GST/HST-exempt financial services.

Counsel to several confidential real estate clients in GST/HST Tax Court appeals and objections to the CRA Appeals Division, in respect of assessments pertaining to the GST/HST self-assessment of newly constructed residential rental buildings and the related new residential rental property rebates.

Counsel to Mr. Jefferson in Jefferson v. The Queen, 2019 TCC 91.

Counsel to Montecristo Jewellers Inc. in Montecristo Jewellers Inc. v. The Queen, 2019 TCC 31.

Counsel to Medallion Corporation in Medallion Corporation v. The Queen, 2018 TCC 157.

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.

Counsel to a confidential client in a GST/HST Tax Court appeal settled prior to the hearing, in respect of an assessment of a financial institution's input tax credit allocation methodology.

Counsel to a confidential client in a director’s liability Tax Court appeal settled prior to the hearing, regarding an assessment for source deductions and GST/HST.

Counsel to numerous confidential clients in respect of assessments of GST/HST and income tax relating to home sales.

Counsel to numerous confidential clients in making voluntary disclosures with the CRA and Ministry of Finance.

Selected Speaking Engagements

Presenter, “Seller Beware! New Canadian Sales Tax Changes for Online Sellers”, AJAG Professional Development, June 11, 2021

Presenter, “Duty of Care Owed to Taxpayers,” Chartered Professional Accountants Commodity Tax Symposium, October 24, 2019

Presenter, “Case Law Update,” Chartered Professional Accountants Commodity Tax Symposium, October 16, 2018

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

Selected Publications

Co-Author, "Canada Country Report," Taxation of Crypto Assets, Wolters Kluwer, November 13, 2020.

Co-Author, “Duty of Care Owed to Taxpayers … And What to Do When Dealings with the CRA Go Sideways,” 2019 CPA Commodity Tax Symposium, October 2019

Co-Author, “Callidus Capital Corporation v. Her Majesty the Queen,” Sales Tax, Customs & Trade, Federated Press, Volume XVI, No. 2, 2019

Co-Author, “Case Law Update: 2018 CPA Commodity Tax Symposium,” 2018 CPA Commodity Tax Symposium, October 2018

Author, “Unsuspecting Applications of Fair Market Value in the Excise Tax Act,” 2015 CPA Commodity Tax Symposium, September 2015 (Awarded the Norman Guérin Award)

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

"Bozzer: An Interesting 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

Insights

Publications Article Dec 01, 2020 Fall Economic Update: Major GST/HST Changes to Non-Resident Businesses Selling to Canadian Consumers
Publications Article Apr 03, 2020 Canada’s Emergency Wage Subsidy Provides Relief to Canadian Corporations
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?

Education

  • 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

Expertise

Industries