David J. Rotfleisch

Tax Law

David Rotfleisch

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

Tax Court orders CRA to release GAAR committee reports about similarly situated taxpayers

Canadian accountant and tax lawyer David J Rotfleisch explains why the Committee's legal analysis fell within within the scope of discovery

The Ontario Ministry Of Finance's Voluntary Disclosures Program – A Canadian tax lawyer's summary

David J. Rotfleisch explores the differences between the federal and Ontario VDPs

Preston Family Trust II v The Queen: Assumptions of facts in replies to a notice of appeal

Just the facts, ma'am: David J. Rotfleisch explains why the Tax Court of Canada would strike out the CRA's legal assumptions in a notice of appeal

New proposed mandatory tax planning reporting obligations under the Canadian Income Tax Act

Amendments to the new rules were made in August 2022 and are likely to become law says Canadian accountant and tax lawyer David J Rotfleisch

Barrs v The Queen: Taxpayer relief under S.220(3.1)

Canadian accountant and tax lawyer David J Rotfleisch on a Federal Court of Appeal case involving a CRA's review officer's failure to engage with a request for equitable treatment

MNR v Zhao: CRA collection action when there are reasonable grounds for delay

Canadian accountant and tax lawyer David J Rotfleisch on the Canada Revenue Agency’s successful jeopardy order in a high-profile BC real estate case

Tax pipeline planning: A Canadian tax lawyer's guide and case study

A pipeline plan is a tool used to avoid paying tax on dividends to pay tax on capital gains explains David J Rotfleisch

FCA overturns Tax Court's decision because the CRA's evidence was about the taxpayer’s spouse

Canadian accountant and tax lawyer David J. Rotfleisch on the Khanna v The Queen decision by the Federal Court of Appeal, which overturned a Tax Court ruling

The Queen v Paletta – The legal test for business income

Tax lawyer and accountant David J. Rotfleisch on the CRA's successful appeal of a Tax Court of Canada ruling regarding foreign currency trading

Zvilna v. The Queen: Director's liability for unpaid taxes, a note of caution to directors

Tax lawyer and accountant David J. Rotfleisch on the successful appeal of a director’s liability assessment before the Tax Court of Canada

Transferring cryptocurrency to a bare trustee or holding cryptocurrency as a bare trustee

Tax lawyer and accountant David Rotfleisch on Canadian cryptocurrency tax planning through the use of bare trusts

A Canadian tax lawyer's guide on net worth assessments – Halls v The Queen, 2022 TCC 14

Canadian accountant and tax lawyer David Rotfleisch on a net worth assessment win for the CRA involving a taxpayer's record keeping

How to use BVI or other offshore non-CCPCs to save tax on investment income

Canadian tax lawyer and accountant David Rotfleisch the risks (and rewards) of the British Virgin Islands tax avoidance strategy

A Canadian tax lawyer's perspective on income tax statute-barred periods

David J Rotfleisch on the timing legalities of reassessments

A Canadian tax lawyer's perspective on Tax Court of Canada minutes of settlement vs. consent to judgment

David J Rotfleisch on settling a dispute prior to a hearing in Tax Court

RRSP double taxation from overcontribution

Tax lawyer and accountant David J Rotfleisch on double taxation and relief

Reeves v the Queen & applicability of the GST/HST new housing rebate

Tax lawyer and accountant David J Rotfleisch on why a homebuyer was denied the new housing rebate by the Tax Court of Canada

Tax Court rules that gift of shares of a private corporation to a foundation was ineligible for a charitable tax credit

Tax lawyer and accountant David J Rotfleisch on gifting non-qualifying securities such as a promissory note to a registered charity

What can a taxpayer do if a CRA decision letter is unclear?

Canadian accountant and tax lawyer David J Rotfleisch on a recent Federal Court decision against Canada Revenue Agency

A Canadian tax lawyer's scary taxes for Halloween

From Halloween candy to the Halloween Massacre, David Rotfleisch on the tricks and treats of recent Canadian tax history

Analysis: Tax litigants may amend their arguments during a trial

Canadian tax lawyer and accountant David J Rotfleisch analyzes Canada v. Pomeroy Acquireco

Canadian income tax - proposed First Home Savings Account

David J Rotfleisch on the Liberals' proposed tax favoured savings account

Dale et al. v the Queen – Timing on issue of shares in Section 85 rollover

Tax lawyer and accountant David J. Rotfleisch on a successful appeal of a Tax Court decision

Contesting a will in Ontario: Canadian tax lawyer guide

Provincial legislations are carefully crafted to include provisions that infringe upon and restrict an individual's testamentary freedom, says tax lawyer and accountant David J Rotfleisch

Electing out of spousal rollover on death

Toronto Tax Lawyer and Accountant David J Rotfleisch explains when, with proper estate planning, it is possible to achieve a substantially better tax outcome