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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:

Man working at a desktop computer with a digital human and brain appearing on the double monitors.

CRA’s Increasing Use of Digital Tools and AI Analytics to Enforce Penalties: What Canadian Taxpayers Need to Know Now

Rear view of people attending a funeral service.

The 7 Steps of Estate Administration in Canada – Guidance from a Canadian tax lawyer

Business owner hanging a sign advising customers that they are closed due to COVID-19.

Agreements Must be in Writing: Hutchings v. The King (2025 TCC 108), a Case of COVID-19 Rent Subsidies

Black legal briefcase on a bench in a courtroom.

Couture v Canada (Revenue Agency) – How Not To Conduct a Judicial Review

Miniature figurines of businesspeople standing on a map of the United States and Canada.

Cross-Border Tax: How Trump’s ‘One Big Beautiful Bill’ (OBBB) will Affect Canadians with American Income, Investments, Business Operations

Two mannequins side-by-side outfitted in luxury clothing

Does Your Job Require You to Buy Luxury Goods? And, Can You Deduct Those Luxury Goods on Your Taxes? The Case of Samotus v The King

The word “shares” spelled out with block letters on top of a paper containing financial data.

Canadian Tax Trap: Section 160 Leads to Derivative Tax Liability for 50-50 Shareholders Who Receive Dividends from a Tax-Debtor Corporation: McCague v The King, 2025 TCC 59

Young woman working on her laptop while sitting in an outdoor café.

A Canadian Tax Lawyer’s Tax Guide For ‘Digital Nomads’ Moving to Canada: What You Need to Know About Canada’s Tax System

Paper with the words “Tax Scam” written on it lying on top of a calculator

A Canadian Tax Lawyer’s Case Commentary on Magren Holdings Ltd. v Canada, 2024 FCA 202: The Application of General Anti-Avoidance Rule (GAAR) on Capital Dividends

A "For Rent" sign in front of a house

Blecha v the King – What Expenses Can Owners Deduct from Rental Properties That Produce No Income?

Get your CRA tax issue solved


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