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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:

Concerned Canadian taxpayer reviewing tax documents while speaking with a CRA call centre representative, with Parliament, the Canadian flag, and audit reports in the background, symbolizing concerns about the accuracy of CRA tax advice and government oversight.

CRA Agents Answer Only 17% of Tax Questions Accurately: What Canadian Taxpayers Must Know About the Auditor General and Ombudsperson Reports

An older man and two younger women at a table with coffee cups looking at and pointing to a laptop.

How to Sell Your Family Business to Your Children Using Bill C-59 ‘Intergenerational Business Transfer Tax Rules’ of the Income Tax Act (ITA)

Young woman in a fashionable outfit shows a peace sign to her smartphone.

Canadian Influencer Tax Guide: CRA Audit Risks, GST/HST Rules, Cryptocurrency Income, Foreign Reporting, and Tax Planning Strategies

A burlap sack of money, globe, and calculator on a wood table.

Why Interest on Foreign Tax Arrears is Not Deductible: Canadian Tax Lawyer Explains Tax Court Decision in Bank of Montreal v. The King, Paragraph 18(1)(a)

AI robot controlling holographic data

From 4% Random Selection to 100% Audit Risk: How CRA’S AI-Driven Audits Are Changing Tax Enforcement for Canadians

2026 FIFA World Cup soccer ball with Canada & USA logo on green grass field.

FIFA World Cup 2026 and Canadian Tax: What Short-Term Renters, Businesses, and Bettors Need to Know

Closeup shot of male hands in handcuffs on a wooden table.

The Clear Line Between CRA’s Tax Audit vs. a Criminal Tax Investigation: Why R v Jarvis is the Most Important Tax Case for Canadian Taxpayers

Judge's gavel in front of vertically stacked books on an old wooden desk

When the CRA Recharacterizes Capital Gains as Business Income: Happy Valley Farms, Stewart v. Canada, and the Legal Framework Governing CRA Tax Audits and Reassessments

Judge holding gavel in courtroom with one hand placed in an open book

Stewart v. Canada: Canadian Tax Lawyer Explains Why Supreme Court of Canada (SCC) Changed ‘Source of Income Test’ to Include Legitimate Business Losses, Unsuccessful Ventures

Man checking stock market data on tablet

Betting on Elections or Sports? How the CRA Taxes Prediction Markets (And Are Your Prediction Market Gains Tax-Free?)

Get your CRA tax issue solved


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