David J. Rotfleisch
Tax Law
Recent Blog Posts By David J. Rotfleisch
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
What to do when the CRA refuses taxpayer relief
Tax accountant and lawyer David J Rotfleisch explains how a corporate director won relief from the CRA over payroll remittance in Maverick v HMK, 2023
Case Commentary: Csak v The King 2024 TCC — Transfers of property while owing taxes to the CRA
David J Rotfleisch explains why the Tax Court of Canada found the Canada Revenue Agency's 1988 and 1989 reassessments statue-barred
Taxpayer sidesteps gross-negligence penalties and $90,000 in taxable income because tax year was statute-barred
As David J Rotfleisch explains, the decision by the Tax Court of Canada in Abbass V The King centred on a bookkeeping error by the taxpayer's accountant
Director held personally liable for unremitted and uncollected GST/HST — due diligence defence judged insufficient
Case commentary from Canadian tax accountant and lawyer David J Rotfleisch on the Tax Court of Canada decision in Hall v The King
Case Commentary: CRA violates procedural fairness for CERB/CRB claims
Canadian tax lawyer and accountant David J Rotfleisch examines the Federal Court decision in Cameron v. Canada (Attorney General) in favour of the taxpayer
Made a mistake on your tax return? Here's how to change your Canadian tax return through the tax objections process
Canadian tax lawyer and accountant David J Rotfleisch explains the legal history behind the tax objections process but cautions against aggressive tax strategies
When is it worth challenging the CRA's defective Tax Court pleadings?
Tax accountant and lawyer David J Rotfleisch reconciles the Federal Court Of Appeal's decisions in the similar but different Preston and Adboss cases
A Canadian tax lawyer explains why the ATIP process is critical to preparing for tax disputes with CRA
An Access to Information or Personal Information (ATIP) request can be a double-edged sword despite its importance to resolving tax matters
Tax complexities in dealing with the death of a spouse: ODSP and child benefits
Canadian tax lawyer and accountant David J Rotfleisch looks at the concept of ghost income in a win for the taxpayer in O'Brien v. The King