David J. Rotfleisch

Tax Law

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

Accepting money from a spouse with tax problems can give you a bigger problem with the CRA

Courts will focus on economic reality, not technical form, when applying anti-avoidance provisions like section 160, explains tax lawyer David J Rotfleisch

When taxpayer relief, CPP limitation periods, and procedural finality abandon fairness without a remedy

Tolley v The King is a reminder that developments after tax reassessments, no matter how convincing, cannot alter relief from reassessments retroactively.

When CRA employees misbehave and make mistakes against Canadian taxpayers

The Canada Revenue Agency distinguishes clearly between employee misconduct and wrongdoing, applying different legal and administrative frameworks to each

CRA introduces software-specific controls for EFILE accounts, a safety feature, starting in 2026

Proactively reviewing EFILE accounts, certified tax software usage, and internal controls will position you far better when the new CRA rules take effect

When judicial review (Federal Court) finds that interest imposed by CBSA must be waived

The decision in Lufthansa Technik Aktiengesellschaft offers guidance on how interest-relief applications must be evaluated under s. 3.3 of the Customs Act

Case Commentary: HMK v. Quebecor Inc – Federal Court Of Appeal rejects GAAR challenge to using strategy of business losses

The FCA decision reaffirmed that tax efficiency alone does not equate to abuse under GAAR, explains Canadian tax lawyer and accountant David J Rotfleisch

How to deduct "loss leaders," other outrageous promotional expenses on your Canadian business taxes

What Canadian tax rules apply to the deductibility of promotional expenses? Lessons from a $3.2 million giant bluefin sale and Japan's ‘Tuna King’ of sushi

Missing a CRA notice is not an excuse: Tax Court reinforces strict deadlines to GST objections

The Tax Court of Canada’s decision in Ng v. The King used a four-step legal test for mailing, explains Canadian tax lawyer and accountant David J Rotfleisch

When CRA reassesses you beyond the normal period for tax shelters for charitable donations

Canadian tax lawyer and accountant David J Rotfleisch explains how a taxpayer involved in a leveraged donation scheme won in Tax Court against the CRA

Case Commentary: Rotfleisch v. Canada – Filing an objection does not stop the alleged tax owing from accumulating interest

Canadian tax lawyer and accountant David J Rotfleisch looks at a Federal Court of Canada decision in a case going back to 2004 in which he was the applicant

Tax evasion, tax compliance, and actual tax collection compared: Italy is worse, while Canada is improving

Italy relies on broad tax amnesty schemes to recover lost revenue; the Canada Revenue Agency prefers the structured, ongoing voluntary disclosure program

When late filing penalties apply under subsection 162(7), one's track record of respecting CRA filing deadlines matters

The recent Tax Court of Canada decision in Laurie v. the King highlights the narrow scope of the due diligence defence in regards to late-filed T1135 forms

Agreements must be in writing: Hutchings v. the King, a case of Covid-19 rent subsidies

Paper, not promises, matter when it comes to government subsidies to businesses during the pandemic, though verbal agreements are customary for some

Couture v Canada (Revenue Agency) — How not to conduct a judicial review

Federal Court applications for judicial review must include essential or minimum elements, facts or legal grounds, indicating unreasonable CRA decisions

When Canadian taxpayers have severe emotional trauma, documentation is key to taxpayer relief requests

The 2025 judicial review of Bifano v Attorney General (2019) demonstrates the need for documentation from psychologists, doctors explains David J Rotfleisch

Case Commentary: Schwarz v. HMK – You must appeal within the deadline for tax reassessments

The Tax Court of Canada cannot forgive tax debt. Its jurisdiction is limited to correctly determining the amount of tax payable explains David J Rotfleisch

Case Commentary: Charlebois v. The King – How NOT to apply for GST/HST rebate for owner-built homes

The CRA can make assumptions that a home is not qualified for a rebate; it is the taxpayer's burden to refute the assumptions, explains David J Rotfleisch

Does your job require you to buy luxury goods? And, can you deduct those luxury goods on your taxes?

Canadian tax lawyer and accountant David J Rotfleisch deconstructs the case of Holt Renfre employee claiming luxury clothing expenses in Samotus v. The King

Section 160 leads to derivative tax liability for 50-50 shareholders who receive dividends from a tax-debtor corporation

Canadian tax lawyer and accountant David J Rotfleisch comments on the section 160 tax trap in the Tax Court of Canada decision in McCague v The King, 2025

Case Commentary: The application of the General Anti-Avoidance Rule on capital dividends

Canadian tax lawyer and accountant David J Rotfleisch looks at the impact the new GAAR may have had on the Magren Holdings case had the rule been in effect

What expenses can owners deduct from rental properties that produce no income?

In Blecha v The King, the Canada Revenue Agency disputed whether a taxpayer was really renting residential property, explains tax lawyer David J Rotfleisch

Bank Of Nova Scotia v The King: How a procedural rule on loss carrybacks triggered $7.9M in interest arrears on tax not owing

It’s a matter of interest as to why Scotiabank is appealing to the Supreme Court of Canada after losing Canada Revenue Agency decisions in the lower courts