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

What are a taxpayer's rights during an access to information and privacy (ATIP) request for their own tax records?

Canadian tax lawyer and accountant David J Rotflesich looks at case law involving requests to the Canada Revenue Agency for disclosure of relevant records

Loupy's: Deemed self-assessment after GST/HST number cancellation

When a taxpayer ceases to be a GST/HST registrant, they can face a significant tax liability, as in the case of Loupy’s Restaurant before the Tax Court of Canada

Case Commentary: Onex Corporation v. Canada, 2024 FC

Section 1247, subsections 220(2.1) and 220(3), of the Income Tax Act can grant relief from tax reassessment and filing requirements, says David J Rotfleisch

How to use "well accepted accounting principles" to your advantage to calculate business or property income for a taxation year

Canadian accountant and tax lawyer David J Rotfleisch explains how accounting standards like GAAP and IFRS pertain to business and personal income taxation

Case Commentary: Glencore v. Canada – How are commitment and break fees in M&A transactions taxed? Windfall or business income?

When the Supreme Court of Canada denied Glencore’s leave to appeal, it ended a 30-year tax dispute, and characterized complex M&A fees as business income

Case Commentary: When can directors, employees, independent contractors claim the small business deduction?

The Supreme Court of Canada recently denied leave to a taxpayer’s unusual appeal of a Tax Court decision, explains Canadian tax lawyer David J Rotfleisch

When can the federal court quash abusive CRA decisions to assess taxes?

In Milgram Foundation, the Federal Court recognized the finality of the CRA's acceptance of a voluntary disclosure application, explains David J Rotfleisch

Employees Beware: Upcoming legislation affecting capital gains will impact employee stock options

David J Rotfleisch explains how Department of Finance changes to legislation, which are expected to be retroactive to June 25, 2024 will affect stock options

Are poker winnings now taxable In Canada? A Canadian tax lawyer's analysis of four Tax Court Of Canada recent poker decisions

When a taxpayer relies on other means to sustain their lifestyle, poker-playing activities fail to comprise a source of income, explains David J Rotfleisch

How lower income individuals can receive valuable tax benefits by using CRA's new free SimpleFile program

The Canada Revenue Agency has invited more than 1.5 million lower- or fixed-income Canadians with simple tax situations to use the SimpleFile pilot program.

Taxpayers Beware: CRA’s new tools for catching tax evasion, avoiding tax debt

As David J Rotfleisch explains, the most recent federal budget included plans to hold tax professionals accountable as well as notices of non-compliance

Guide to Canadian tax rules on benefits arising from use of corporate assets (e.g., money, trips, boats, cars, space trips, etc.

What happens when business owners dip into their corporation's pockets to pay for personal expenses? Potentially dire consequences, says David J Rotfleisch

What does Tax Court decide? What does Federal Court decide? Supreme Court clarifies jurisdictions

Through its decisions on Dow Chemical and Iris Technologies, the Supreme Court of Canada has clarified tax appeal jurisdictions, explains David J Rotfleisch

When can discovery answers of a deceased Canadian be used under subsections 100(6)-(7) of the Tax Court Of Canada rules?

Canadian accountant and tax lawyer David J Rotfleisch on a Tax Court decision involving the testimony of a taxpayer who died soon after discovery

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