David J. Rotfleisch
Tax Law
Recent Blog Posts By David J. Rotfleisch
Losses, expenses arising from transactions that are not 'sufficiently commercial' may be ineligible to reduce your income tax
Canadian tax lawyer and accountant David J Rotfleisch explains why the Tax Court dismissed the FX trade case of a successful businessman in Chad v The King
How the CRA uses 'nudge letters' with online sellers to increase uptake of Canada's VDP
Canada Revenue Agency uses nudge letters to prompt taxpayers to review their tax affairs, ensure compliance, and access the Voluntary Disclosures Program
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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