Lawyer Profile
Angelo Gentile
Toronto, Ontario
Overview
Angelo is Co-Leader of the firm's Tax Controversy/Tax Litigation Group and a member of the Tax 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, as well as the 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 instils 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.
Practice Areas
Bar Information
Called to the bar: 2007 (ON)
Professional Details
Education
LLM, University of California, Berkeley, School of Law, 2014 JD (Hons.), University of Toronto, 2006 B.A.Sc. Industrial Engineering (Hons), University of Toronto, 2003
Associations
Memberships Canadian Bar Association (Commodity Tax Customs and Trade Section) GST Leaders Forum, a group established by the CPA of the most prominent GST/HST accountants and lawyers from across Canada 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
Articles & Speeches
Co-Presenter, "GST/HST - An Update and Review for the Non-Specialist," Ontario Tax Conference, October 28-29, 2024. Presenter, "Indirect Tax Update for Non-Indirect Tax Practitioners," Canadian Tax Foundation 74th Annual Tax Conference, November 27-29, 2022. Presenter, "Seller Beware! New Canadian Sales Tax Changes for Online Sellers," AJAG Professional Development, June 11, 2021. Co-Author, "To Claim or Not to Claim - The New Age for Input Tax Credit Controversy," Tax Profile , December 2024. Co-Author, "Canada Revenue Agency Extends Filing Deadline for Underused Housing Tax - Again," Aird & Berlis LLP, October 31, 2023. Co-Author, "Beginning of a New Rental Construction Boom? Temporary GST Exemption for Purpose-Built Residential Rental Properties Sparks Growth Potential," Aird & Berlis LLP, September 28, 2023.
Selected Decisions
Represented the Appellant before the Tax Court of Canada in Amicarelli v. The King, 2025 TCC 185, achieving a precedent-setting decision on the deductibility of Bitcoin losses from theft/fraud. Represented Closing the Gap Healthcare Group Inc. in the sale of all issued and outstanding shares to Extendicare Inc. for $75.5 Million. Represented multiple produce companies in connection with a hybrid sale of shares and assets for more than $100 million. Represented an international media company in its acquisition of Canadian online film and television streaming assets. Represented Powerfleet, Inc. (Nasdaq: AIOT), a global AIoT SaaS provider, in its acquisition and related financing of Fleet Complete, a leader in connected vehicle technology and fleet management. Acted for Knightstone Capital Management in the sale of a 20 per cent equity share in the CampusOne residence in Toronto. Advised Phillips Foods Inc. , a U.S.-based global processor and distributor of branded seafood products, in the acquisition of the assets of South Shore Seafoods Group of Companies, a Canadian seafood processor and distributor.