David J. Rotfleisch

About the LawyerDavid J. Rotfleisch is one of Canada’s most experienced and credentialed tax lawyers, bringing over 35 years of tax litigation, planning, and dispute-resolution expertise to clients across the country. He is a founding Canadian tax lawyer and one of only 16 Ontario Certified Specialists in Taxation as of 2026. A rare dual-qualified professional, he is both a lawyer and a Chartered Professional Accountant and has completed the esteemed CICA In-Depth Tax Course, allowing him to blend legal strategy with accounting precision.Based in Toronto, David is the founding tax lawyer of Taxpage.com / Rotfleisch & Samulovitch P.C., a boutique Canadian tax law firm established in 1987 that focuses on income tax disputes and related controversy work. His practice encompasses the full spectrum of contentious Canadian tax matters, including CRA tax audits and investigations, tax reassessments, tax litigation, and voluntary disclosures. He regularly represents individuals and businesses before the Canada Revenue Agency and the Tax Court of Canada, handling complex and often high-stakes disputes involving income tax, GST/HST, international tax compliance, and cryptocurrency-related tax controversies.David’s practice spans the full spectrum of Canadian income tax and cryptocurrency taxation. He advises Canadian taxpayers, start-ups, resident and non-resident business owners, corporations, and high-net-worth individuals on matters ranging from routine compliance to highly complex tax and estate planning. Over his extensive career, he has represented several clients in voluntary disclosures, tax audits, and every stage of tax dispute resolution and litigation.With additional professional experience in the computer and IT industry, David brings technical insight into blockchain systems, smart contracts, crypto business models, and the legal challenges of emerging technologies. This combination of deep tax proficiency and digital-asset expertise uniquely positions him to advise innovation-driven businesses operating across both traditional and digital economies, particularly when their activities give rise to contentious or litigated tax positions.ExperienceDavid has practiced tax law continuously for well over three decades, with more than 35 years devoted primarily to Canadian tax controversy and related advisory work. He became a chartered accountant in 1977, was called to the Ontario bar in 1983, and founded his tax law firm in 1987. Since then, he has developed a national practice focused on resolving disputes with the Canada Revenue Agency and litigating tax matters before the Tax Court of Canada and other judicial forums.As a founding partner of Rotfleisch & Samulovitch P.C., David has overseen a wide range of contentious tax files for entrepreneurs, privately held corporations, multinational businesses, resident and non-resident taxpayers, and high-net-worth individuals. His work frequently involves CRA tax audits, objections, appeals, and negotiated settlements, as well as fully contested hearings when litigation is required. He is deeply experienced in disputes involving income tax, GST/HST, director liability, penalties, offshore reporting failures, and the taxation of cryptocurrency and other digital assets.David has extensive experience guiding clients through the Voluntary Disclosures Program in circumstances involving serious tax non-compliance, unreported offshore income, and failures to file required returns or information forms. His background as both a lawyer and CPA allows him to analyze complex financial records, reconstruct disputed transactions, and present technically sound positions in both negotiations with CRA and formal litigation. He has also provided expert tax opinions in the context of broader commercial and estate disputes, where tax treatment and potential CRA challenges are central issues.SpecialtyDavid’s practice is concentrated on Canadian tax litigation and tax controversy, with a strong emphasis on defending taxpayers in disputes with the Canada Revenue Agency and, when necessary, before the courts. Within the broader field of tax law, his key focus areas include:

• Tax Dispute Resolution and Litigation: Representation at all stages of the dispute process, from audit and internal CRA appeals to Tax Court of Canada proceedings and related negotiations, including settlements and consent judgments.
• CRA Tax Audits and Investigations: Advising and representing clients during income tax and GST/HST audits, net-worth and lifestyle audits, and more intensive CRA investigations arising from suspected non-compliance or aggressive tax positions.
• Voluntary Disclosures (Tax Amnesty): Assisting individuals and businesses with voluntary disclosures to correct past non-compliance, reduce penalties and interest exposure, and mitigate the risk of prosecution.
• Corporate & Business Tax Controversy: Handling disputes involving corporate reorganizations, shareholder loans, director liability assessments, cross-border transactions, and the tax treatment of complex business structures.
• Estate and Succession-Related Tax Disputes: Addressing contentious income tax and related issues arising from estate freezes, succession planning structures, and post-mortem tax assessments.
• Real Estate Taxation Disputes: Advising on contested assessments involving the income tax and GST/HST treatment of real estate development, residential and commercial property sales, and short-term rental activities.
• Crypto Taxation and Digital-Asset Controversy: Representing taxpayers in disputes involving cryptocurrency trading, staking, decentralized finance arrangements, and cross-border crypto holdings, including CRA audits and reassessments targeting digital-asset transactions.
• International and Offshore Tax Compliance Disputes: Managing controversies involving foreign income reporting, offshore structures, non-resident taxation, and the tax implications of immigrating to or emigrating from Canada.

Education

• J.D., Osgoode Hall Law School
• B.Com., McGill University

• Chartered Professional Accountant (CPA), Canada
• CICA In-Depth Tax Course

• Member, Canadian Bar Association
• Member, Law Society of Ontario
• Chartered Professional Accountant (Lifetime Member), Canada

• Awards
  • Taxpage announced the 5th edition of “Canadian Tax Facts” in which David J. Rotfleisch is described as the author and a leading Canadian tax lawyer.
  • Global Law Experts notes an “Award – Best Tax Blog in Canada – September 2025” in connection with David J. Rotfleisch / Taxpage.
• Industry rankings
  • Listed by Global Law Experts as one of Canada’s most experienced and credentialed tax lawyers, and identified as one of only 16 Ontario Certified Specialists in Taxation as of 2026.
• Leadership roles
  • Founding Canadian tax lawyer at Taxpage.
  • Founding lawyer of Tax Lawyers Canada / Taxpage core team.
• Major case successes
  • Featured as “Founding tax lawyer David J Rotfleisch, JD, CA, CPA” in Mondaq coverage of settlements and damage awards for wrongful dismissals.
• Contributions to award-winning projects
  • Authored the fifth edition of “Canadian Tax Facts,” a compiled reference resource for reporters, editors, and producers.
  • Named in connection with Taxpage’s “Best Tax Blog in Canada” recognition.