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David Rotfleisch and Enchantee

David J. Rotfleisch

CPA, JD


David J. Rotfleisch, a leading Canadian tax lawyer, is not only a certified specialist in taxation but also a chartered professional accountant. Most recently, David is a pioneer in Canadian crypto taxation.

Known for his dual expertise in income tax law and technology, David has a comprehensive background in the computer and IT industry, making him effective and efficient in handling high-tech tax legal issues in software development and intellectual property.

He has served various resident and non-resident businesses and individuals, dealing with matters from simple tax planning to complex estate planning, voluntary disclosure, crypto taxation and tax litigation.

A graduate of McGill University and Osgoode Hall Law School, David became a chartered accountant in 1977 and was admitted to the Ontario bar in 1983. He founded his tax law firm in 1987.

David is the Canadian Tax lawyer that LAW360 (LexisNexis), Canadian Accountant, and international legal publisher MONDAQ turn to for commentary on Canadian taxes.

He is also a prolific blogger and has frequently appeared on radio, TV, and various print and online media who seek his insight and expertise on Canadian tax problems.

As of April 2020, he was one of 12 Ontario Certified Specialists In Taxation™.

Posts by David J. Rotfleisch:

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Tax Lawyer-Client Confidentiality May Fail to Protect End-Product Tax Documents, says Federal Court of Appeal: BMO Nesbitt Burns Inc. v Canada, 2023 FCA 43

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Independent contractors like cab drivers can be deemed employees even if they file taxes as “self-employed”: Beach Place v. Employment Standards Tribunal (2022)

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Everything Canadians Need to Know About Unexercised Employee Stock Options: Income Tax Liabilities, Dispositions, Buyouts and Cancellations

“Tax Facts 2023” Released By Canadian Tax Lawyers Rotfleisch & Samulovitch

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When CRA reassessed a taxpayer’s tax returns beyond the normal reassessment period: Goldhar v The King, 2023 TCC 30

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Canadian taxation of U.S. not tax-deductible: Roth IRAs and 401(k) accounts

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Federal government introduces new trust reporting rules to take effect in 2023 taxation year – Trustees need to be prepared.

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Everything You Need To Know About The Underused Housing Tax (2024) On Vacant Or Underused Housing In Canada

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Guide to the Canadian Tax Treatment of Halal Mortgages: Halal Mortgages are Shari’ah-compliant but Taxable in Canada

Gordon et al v The King: CRA’s investigation on SR&ED tax credits cannot use its civil tax audit power to gather information for a criminal investigation

Get your CRA tax issue solved


Address: Rotfleisch & Samulovitch P.C.
2822 Danforth Avenue Toronto, Ontario M4C 1M1