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

Case Analysis: Why a business must demonstrate actual business activities before applying for business tax deductions
David J Rotfleisch examines the case of a chartered professional accountant who claimed business expenses for a company he cofounded in Prince Edward Island
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Tax Court Of Canada is not ‘slap-dash,' nor tolerates sloppy examination for discovery
David J Rotfleisch explains why the Tax Court of Canada, in Whistler Blackcomb Holdings Inc. v The King, 2025, dismissed the CRA's motion for a new nominee
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Loss-trading transactions to avoid paying tax disallowed by Tax Court Of Canada (GAAR rule)
In Total Energy Services v. HMK, the FCA upheld a Tax Court ruling that complex transactions satisfied three conditions of the general anti-avoidance rule
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Case Commentary: Ayre v the King – Convoluted charitable gifts made through questionable financing transactions
Canadian tax lawyer and accountant David J Rotfleisch examines donative intent under Section 118.1 of the Income Tax Act in a pharmaceutical donation case
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Case Commentary: Canada v. Csak – Why filing a waiver for a tax reassessment must be done within the normal reassessment period
Closing a dispute that had lasted for more than 10 years, the Federal Court of Appeal overturned a Tax Court waiver decision, explains David J Rotfleisch
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Case Commentary: Onischuk v. The King – Tax Court rules cannot override CRA's statutory requirements
A nil assessment is an objection exception because it is not an assessment and hence cannot be objected to or appealed from, explains David J Rotfleisch
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Case Commentary: Uppal Estate v. the King upholds procedural fairness for Canadian taxpayers in tax litigation
The decision emphasizes the duty of the CRA in Tax Court pleadings and serves as a procedural safeguard for Canadian taxpayers explains David J Rotfleisch
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A widow is not a spouse: Canadian court saves widow from the CRA's $100,000 derivative tax assessment
In Enns V Canada, 2025 FCA 14, the timing of an RRSP transfer was critical to the decision, explains Canadian accountant and tax lawyer David J Rotfleisch
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Case Commentary: Yadgar v. The King — When trusting your accountant 100% is not an acceptable defence in the Tax Court Of Canada
Canadian tax lawyer and accountant David J Rotfleisch explains how an immigrant success story went wrong in the Tax Court of Canada and the court of appeal
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Case Commentary: How the CRA abused the voluntary disclosure process for this Canadian taxpayer
The Canada Revenue Agency proposed to reassess the Milgram Foundation after accepting its voluntary disclosure application thus prompting a judicial review
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When can Canadian taxpayers apply to reopen a trial at the FCA from the Tax Court?
As Canadian accountant and tax lawyer David J Rotflesich explains, reopening a court case depends upon the introduction of fresh evidence and error of law
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How to dispute your tax assessment under Toronto's 2024 Vacant Home Tax
A hundred thousand tax assessments were reversed in 2023, but the City of Toronto has taken concrete steps to revamp the VHT regime for the 2024 tax year
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Six strategies to minimize probate fees in your estate plan
These succession planning strategies can be cost-effective and save large amounts of tax that would otherwise be payable upon admitting the will to probate
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Taxpayer's failure to review tax return contributed to negligence, Tax Court Of Canada finds
The CRA can reassess a taxpayer beyond the normal reassessment period if tax return misrepresentations are due to carelessness, neglect or willful default
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Case Commentary: Watts v the King, 2024 TCC 100 — Enhanced costs of litigation
A recent Tax Court of Canada judgment shows why litigants should be aware of all potential court costs asserts tax lawyer and accountant David J Rotfleisch
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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.
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