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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 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?)

Confused man on the phone and holding papers in front of a laptop in a desk

Canada’s Tax Act is Too Complex: Complaints about CRA Rise 27% Despite Recent Automated Tax Filing, Call Centre Failures, Processing Delays, Poor Communication

Silhouette of woman posing at sunrise at the beach.

The OnlyFans Audit: Why a Canadian Tax Lawyer Warns Creators That the CRA Is Watching (for Income Tax Due)

Top view of a judge's gavel, book and an arrangement of different denominations of Euros.

Curran v The King (2026 TCC 79): The Fatal Consequences (and Hefty Penalties) of Pseudo-Legal Tax Arguments

Two men in an office wearing business suits shaking hands.

Restrictive Covenants in Business Sales or Share Sales: How to Navigate the Default Rule, plus Statutory Relief from CRA

Canadian T3 tax form for trust income on a table with Canadian $100 dollar bills, a calculator, pen, and a paper clip.

How CRA Taxes U.S. ‘Profits Interests’ – Canadian Tax Lawyer Explains How to Avoid Double Taxation

A Jar labelled Savings on a table beside four variously-sized stacks of coins.

Why the Federal Court of Appeal Upheld 100% Tax on TFSA Advantages: Canadian Tax Lawyer Analyzes Hunt v. Canada, 2026 FCA 88

Bartender wearing an apron cleaning a shot glass.

Malek v The King (2026 TCC 84): Net Worth Assessments, Gross Negligence Penalties, and the Risks of Poor Tax Compliance in Canadian Owner-Managed Businesses

An interior view of two empty, connected rooms in a home.

Toronto’s Vacant Home Tax: A Complete Guide to Tax Exemptions, Tax Appeals, and Tax Compliance for Toronto Property Owners

Close-up of businesspeople handshake

When the CRA Backs Out of a Deal: Yes, You Can Enforce a Tax Settlement—Lessons from Zhang v. The King (2026 TCC 71)

Get your CRA tax issue solved


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