Amanda Heale

Amanda Heale

Partner, Tax

Toronto

(416) 862-6780 

[email protected]

Bar Admission: Ontario, 2005

Home People

Areas of Expertise

Tax Disputes
International Tax
Tax Litigation
Transfer Pricing
Banking and Financial Services
Tax Advisory Services
Tax

Amanda advises multinational clients navigating complex and multi-faceted tax issues and represents them in high-risk audits and disputes. She leads Osler’s Transfer Pricing practice and has been involved in some of Canada’s most significant disputes in this area.

Amanda is a member of the Executive of the CBA Taxation Section and the CPA-CBA Joint Committee on Taxation. In 2004-2005, she was a law clerk to the Honourable Morris J. Fish of the Supreme Court of Canada.

Amanda taught International Tax for several years at the University of Toronto Faculty of Law. Her thought leadership has been featured in leading industry publications, including Bloomberg Law, International Tax Highlights, Tax Notes International and International Tax Review, and she is a frequent speaker at tax conferences and seminars.

Amanda is a member of Osler’s Partnership Board.

Areas of Expertise

Banking and Financial ServicesInternational TaxTaxTax Advisory ServicesTax DisputesTax LitigationTransfer Pricing

Representative Work

  • A multinational group in the resolution at the CRA administrative level of a significant, multi-year dispute about the transfer pricing of intangibles.
  • A multinational group in the negotiation of a complex bilateral advance pricing arrangement.
  • Wheaton Precious Metals in the out-of-court settlement of its significant transfer pricing dispute with the CRA.
  • Cameco Corporation in the Tax Court of Canada and the Federal Court of Appeal in the first case to consider the interpretation and application of the transfer pricing “re-characterization” rules in paragraphs 247(2)(b) & (d), playing a lead role in formulating the taxpayer’s successful legal theory.
  • Hydro One Limited in its $1.97 billion secondary offering of common shares.
  • Hydro One Limited in its $1.83 billion Initial Public Offering
  • TD Bank in connection with Air Canada’s acquisition of Aimia Canada
  • McKesson Canada Corporation in its transfer pricing appeal to the Federal Court of Appeal (settled out of court).
  • GlaxoSmithKline in the first transfer pricing appeal heard by the Supreme Court of Canada, regarding the transfer price of the active ingredient in a branded pharmaceutical product.
  • Valeant Pharmaceuticals Inc. in its $8.7 billion all cash acquisition of Bausch + Lomb.

Awards and Recognition

  • Chambers Canada: Canada’s Leading Lawyers for Business: Recognized in Tax: Litigation
  • Chambers Global: Canada’s Leading Lawyers for Business: Recognized in Tax: Litigation
  • Lexpert Special Edition: Recognized in Litigation; Insolvency and Restructuring
  • International Tax Review World Tax 2022-2026: Recognized as a leader in Tax Controversy, Women in Tax
  • The Canadian Legal Lexpert Directory: Recognized as Consistently Recommended in Corporate Tax and as Repeatedly Recommended in Litigation – Corporate Tax
  • Lexpert Rising Stars: Leading Lawyers Under 40: Recognized as a Rising Star
  • Best Lawyers in Canada: Recognized in the area of Tax Law
  • Euromoney Americas Women in Business Law Awards: Recognized as a Rising Star in the area of Tax
  • IFLR1000 Rising Stars Awards Americas 2022: Recognized as a ‘Rising Star’ in Tax Dispute Resolution
  • Who’s Who Legal: Recognized in Corporate Tax – Controversy; Canada – Corporate Tax
  • Legal 500: Recognized as a Next Generation Partner in Tax

Media Mentions

  • Media Mentions March 27, 2026

    Canada’s new transfer pricing law puts taxpayers ‘on notice’ – Bloomberg Law News

    Canada’s new transfer pricing law is certain to increase the scope and intensity of CRA audits and controversies, says Amanda Heale.

    Read more
  • Osler News November 14, 2025

    Osler recognized as a Tier 1 firm in ITR’s World Tax 2026

    Osler has once again earned coveted Tier 1 rankings across all four categories.

    Read more
  • Osler News October 1, 2025

    Osler lawyers recognized in Lexpert Special Edition: Restructuring and Insolvency 2025

    Osler is proud to announce that 23 of our lawyers are recognized in the Lexpert Special Edition: Restructuring and Insolvency 2025. This prestigious...

    Read more
  • Media Mentions April 9, 2025

    ‘No avenue for effective judicial oversight’ – International Tax Review

    A recent Tax Court of Canada transfer pricing (TP) decision underlines frustrations that taxpayers may face because of the split legal jurisdiction...

    Read more
View all

Credentials

Education

  • University of Toronto, J.D. (Silver Medallist, Dean’s Key Recipient)
  • Queen’s University, B.A.H. (English Literature)

Languages

  • English

Professional Affiliations

  • Law Society of Ontario
  • Canadian Bar Association
  • Ontario Bar Association
  • Canadian Tax Foundation
  • International Fiscal Association, Canadian Branch Council Member 
  • CBA-CPA Joint Committee on Taxation
  • The Advocates’ Society
  • Canadian Petroleum Tax Society

Osler is a leading business law firm practising internationally from offices across Canada and in New York. Our clients include industry and business leaders in all segments of the market and at various stages in the growth of their businesses. We have built our reputation on our commitment to our clients' success and the experience, expertise and collaborative approach for which we are recognized. We believe that our success is a reflection of our clients' success.