David J. Rotfleisch
Tax Law
Recent Blog Posts By 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
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