David J. Rotfleisch

Tax Law

David Rotfleisch

David J. Rotfleisch, CPA, CA, JD, is the founding Canadian tax lawyer of Rotfleisch & Samulovitch, P.C., a Toronto-based boutique income tax law firm (Taxpage.com). With over 30 years of experience as both a lawyer and chartered professional accountant, he has helped start-up businesses, resident and non-resident business owners and corporations with their tax planning, with will and estate planning, voluntary disclosures and tax dispute resolution including tax litigation. Contact David at david@taxpage.com.

Recent Blog Posts By David J. Rotfleisch

What is the standard of review for discretionary decisions of the CRA appealed to the federal courts?

Canadian accountant and tax litigation lawyer David J Rotfleisch takes a deep dive into the standards for judicial review of taxpayer appeals to the Federal Courts

Federal Court Of Appeal overturns GAAR assessment on the existence of alternative transactions

Canadian tax accountant and lawyer David J Rotfleisch explains why the FCA quashed a Tax Court of Canada decision involving a CRA GAAR abuse analysis

Case Commentary: Persaud v The King – When can you claim tax deductions (Including medical bills) for dependants?

Tax residence is key, says Canadian tax accountant and lawyer David J Rotfleisch, to claiming medical expense deductions for dependents under the Income Tax Act

Tax Court Of Canada rejects CRA's attempt to apply gross-negligence penalties in statute-barred years

Canadian accountant and tax lawyer David J Rotfleisch looks at the case of an Alberta restauranteur and an inheritance in Fuhr v. The King

How international athletes are taxed in Canada: Toronto Maple Leafs' captain John Tavares embroiled in tax litigation with CRA

Tavares is a high-profile opportunity for the CRA to test the limits to the structuring of athlete salaries explains Canadian accountant and tax lawyer David J Rotfleisch

Case Commentary: Cassidy v Canada — using extraordinary circumstances, CRA's delays, inability to pay, or financial hardship

Why the Federal Court, in Cassidy v Canada, ruled that a CRA officer's decision was unreasonable, and the taxpayer received relief over unpaid taxes

What to do when the CRA refuses taxpayer relief

Tax accountant and lawyer David J Rotfleisch explains how a corporate director won relief from the CRA over payroll remittance in Maverick v HMK, 2023

Case Commentary: Csak v The King 2024 TCC – transfers of property while owing taxes to the CRA

David J Rotfleisch explains why the Tax Court of Canada found the Canada Revenue Agency's 1988 and 1989 reassessments statue-barred

Taxpayer sidesteps gross-negligence penalties and $90,000 in taxable income because tax year was statute-barred

As David J Rotfleisch explains, the decision by the Tax Court of Canada in Abbass V The King centred on a bookkeeping error by the taxpayer's accountant

Director held personally liable for unremitted and uncollected GST/HST — due diligence defence judged insufficient

Case commentary from Canadian tax accountant and lawyer David J Rotfleisch on the Tax Court of Canada decision in Hall v The King

Case Commentary: CRA violates procedural fairness for CERB/CRB claims

Canadian tax lawyer and accountant David J Rotfleisch examines the Federal Court decision in Cameron v. Canada (Attorney General) in favour of the taxpayer

Made a mistake on your tax return? Here's how to change your Canadian tax return through the tax objections process

Canadian tax lawyer and accountant David J Rotfleisch explains the legal history behind the tax objections process but cautions against aggressive tax strategies

When is it worth challenging the CRA's defective Tax Court pleadings?

Tax accountant and lawyer David J Rotfleisch reconciles the Federal Court Of Appeal's decisions in the similar but different Preston and Adboss cases

A Canadian tax lawyer explains why the ATIP process is critical to preparing for tax disputes with CRA

An Access to Information or Personal Information (ATIP) request can be a double-edged sword despite its importance to resolving tax matters

Tax complexities in dealing with the death of a spouse: ODSP and child benefits

Canadian tax lawyer and accountant David J Rotfleisch looks at the concept of ghost income in a win for the taxpayer in O'Brien v. The King

Canada Revenue Agency claws back $458 million in CEWs wage subsidies from COVID-19 pandemic following audits

The CRA found cases of aggressive non-compliance among claimants using third parties for application preparation, explains Canadian tax lawyer David J Rotfleisch

Canadian taxpayers must respond to CRA about assessments, reassessments, confirmations by the deadline

In Oliveira v. The King, the Tax Court was primarily concerned with the timeliness of the application, explains Canadian tax accountant and lawyer David J Rotfleisch

Taxpayers must articulate reasons for not responding to questions in motions in Tax Court

Quigley v The King outlines the appropriate questions and responses during the discovery stage, explains tax lawyer and accountant David J Rotfleisch

Tax obligations for foreign home buyers In Canada: Bakhtiari v British Columbia

Can a refugee avoid paying the foreign buyer’s tax on human rights grounds under the Canadian Constitution? David J Rotfleisch comments on the Bakhtiari case

Canadian taxpayers, beware: The CRA gets away with defective pleadings during tax litigation

In Canada v. Preston, the Federal Court of Appeal sided with the Canada Revenue Agency and overturned the Tax Court's decision, over the issue of assumptions

Are hybrid sales of private businesses still a viable tax planning tool for business owners?

David J Rotfleisch explores whether the Foix decision by the FCA radically undermines the tax benefits of a hybrid sale when selling a private business

A Canadian tax lawyer's guide to the In-Trust-For (ITF) Account

Canadian tax accountant and lawyer David J. Rotfleisch discusses ITFs, including tax implications, issues and alternatives to these unregistered investment accounts

Canadian taxpayer involved in a bad will investment scheme granted additional relief on accrued interest

Relief requests beyond the statute of limitation may still be available, depending on the circumstances, explains tax accountant and lawyer David J Rotfleisch

Tax fraud and tax evasion in the same case: Analysis of Regina v Reynolds

A case before the BC Supreme Court included violations of the Income Tax Act and Excise Tax Act explains Canadian accountant and lawyer David J Rotfleisch

SR&ED Tax Credits upheld by Tax Court Of Canada in Canafric Inc. v. The King

Developing new recipes qualifies for Scientific Research and Experimental Development credits, explains David J Rotfleisch, when you make frozen pies