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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:

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

Closeup of opposing lawyers facing each other, holding papers in front of a judge

Landmark Canadian Tax Law Decision that Limits CRA’s Authority Under Section 231.2 of Income Tax Act: Canada (National Revenue) v Shopify Inc., 2025 FC 968

Closeup of a person wearing a suit holding a magnifying glass to a chart with one hand while using a calculator with the other.

Can CRA Require a Taxpayer to Prepare Net Worth Audit Schedules Under the New Section 231.1?

Elderly couple looking at a life insurance policy on a laptop with one pointing at the screen

Canadian tax consequences of a foreign life insurance policy: CRA’s Form T1135 and reporting requirements – Canadian tax lawyer explains what you need to do

Close-up portrait of a man showing an empty wallet

How an Heir was Taxed 75% by the UK, Spain on his Inheritance (Just Crumbs Left) and How Tax Treaties Prevent Double Taxation

Smiling woman wearing an apron holding a clipboard and pen standing in front of shelves full of pottery.

Case Analysis: Why a Business Must Demonstrate Actual Business Activities Before Applying for Business Tax Deductions – Lienaux v. The King

Closeup of a person wearing a suit at a desk holding a tablet looking at a health plan

How are Group Benefit Plans Taxed for Employers? How are Group Benefits Taxed for Employees? What is Taxable? Non-Taxable?

Get your CRA tax issue solved


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