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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:

People at a shareholder's meeting wearing business attire, sitting around a table with documents.

The CRA issues a new ‘Income Tax Folio’ on How Shareholder Loans and Debts are Treated

Closeup of a woman in a dress shirt at a desk with paperwork using a calculator and a pen

When Can Businesses Deduct Interest Payments? A Primer from a Canadian Tax Lawyer

Couple holding paint brushes in a home under renovation

When full business income tax, other than capital gains tax, is payable if business activities are based on a “secondary intention” tax law doctrine in an “adventure in the nature of trade” – guidance from a Canadian tax lawyer

Canadian flag with stacked coins on a world map.

Cancelling Canada’s Digital Services Tax Creates Immediate Logistical Problems at CRA; Don’t Expect a Refund Soon if You Have Pre-Paid

Closeup of man and woman sitting at a desk across from each other with financial documents between them.

How CRA Conducts Net Worth Audits and Enforces Gross Negligence Penalties Against Canadian Taxpayers: Lessons from Mann v. The King and Other Cases

Woman leaving an office with her belongings in a box with her boss drinking coffee in the background

How the Income Tax Act Treats Settlements and Damage Awards for Wrongful Dismissals

A cinematic still of a high-stakes poker game unfolding in a dimly lit, opulent backroom.

How are Professional Poker Winnings Taxed in Canada? Taxable Business Income and Non-Taxable Hobbies: Fournier-Giguère v. Canada et. al., 2025 FCA 112

A professional infographic illustrating Canadian tax reporting requirements for trusts.

A Canadian Tax Lawyer’s Guide to Changes in Tax Obligations for Trust Executors and Trustees that will Simplify Estate Administration

Infographic depicting Income Tax Act section 51 reorganization.

A Canadian Tax Lawyer’s Guide to s.51 Rollovers: What and How Shareholders Can Convert Equity into New Shares Without Capital Gains

A photograph of a document titled 'Judicial Review Application of CRA Decision' lying open on a mahogany desk.

When the CRA Says, “No”: Exploring Judicial Review for Denied Taxpayer Relief from Penalties, Interest Payments on Tax Debt

Get your CRA tax issue solved


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