David J. Rotfleisch
David J. Rotfleisch, CPA, JD is a senior Canadian income tax lawyer with over 38 years of experience representing individuals and businesses in complex income tax matters involving the Canada Revenue Agency (CRA). A Certified Specialist in Taxation (Law Society of Ontario) and a Chartered Professional Accountant (CPA, Lifetime Member), David brings a seldom seen dual perspective to income tax planning, CRA income tax audits, CRA reassessments, CRA tax collections, and tax litigation – combining rigorous legal advocacy with deep accounting and financial analysis.
As the founding lawyer of Rotfleisch & Samulovitch P.C., David has built a national reputation for resolving high-risk income tax disputes, including aggressive CRA tax audits, net-worth and lifestyle assessments, unreported income cases, and multi-year reassessments. His CPA background allows him to dismantle flawed CRA tax audit assumptions, reconstruct income accurately, and challenge CRA methodologies at both the audit and objection stages.
David routinely represents taxpayers in CRA Notices of Objection, negotiating reversals of reassessments, penalty relief, and interest reductions. When disputes escalate, he is an experienced advocate in income tax litigation, with a strong record of successfully defending taxpayers against CRA assessments, collections actions, and allegations of tax fraud or gross negligence.
In addition to dispute resolution, David advises on forward-looking income tax planning for owner-managed businesses, professionals, and high-net-worth individuals, helping clients reduce exposure to future audits and enforcement. His practice also includes defending clients facing wage garnishments, bank account freezes, and director liability claims arising from CRA collection efforts.
A prolific tax commentator, David writes extensively on Canadian income tax law, CRA audit trends, tax litigation strategy, and enforcement developments. He is frequently cited in professional publications and featured in mainstream media, radio, and television, and is widely regarded as one of Canada’s leading authorities on income tax disputes with the CRA.
Education / Qualifications
- Certified Specialist in Taxation, Law Society of Ontario
- Founder, Rotfleisch & Samulovitch P.C. (1987)
- Called to the Ontario Bar (1983)
- JD, Osgoode Hall Law School – completed all available tax courses
- Chartered Accountant (CA), achieved in 1977; now CPA (Lifetime Member)
- Bachelor of Commerce (B.Com.), McGill University (1975)
- CICA In-Depth Tax Course – completed all levels
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Phone: 416-367-4222 Email: david@taxpage.com
Company Profile
Founded in 1987, Rotfleisch & Samulovitch P.C. is a premier Toronto‑based boutique Canadian tax law firm recognized for its expertise in income tax, business law, digital assets/cryptocurrency, dispute resolution, the Canadian Voluntary Disclosure Program (VDP), and other tax-related matters. With deep knowledge of the Canadian tax system, we help taxpayers, businesses, and organizations resolve sophisticated tax issues with clarity and confidence.
Our Comprehensive Tax Services
We provide expert legal support across the full spectrum of Canadian tax matters.
Our services include:
- Strategic tax planning for businesses, self-employed professionals, corporations, organizations, and charities to optimize tax obligations and maximize compliance.
- Proper tax structuring for start-ups, mergers and acquisitions, and corporate reorganizations, including rollovers, estate freezes, and amalgamations.
- Voluntary Disclosure and compliance solutions to correct past filings, report unreported income or offshore assets, and reduce penalties or prosecution risk.
- Cryptocurrency tax guidance on reporting, compliance, and strategic planning for crypto holdings and other digital assets in accordance with CRA regulations.
- Representation in CRA tax audits, investigations, objections, and Tax Court litigation to challenge incorrect or unfair assessments.
- Tax Dispute Resolution & Litigation, challenging incorrect, unfair, or excessive tax assessments, and advocating for clients in the Tax Court of Canada when disputes cannot be resolved with the CRA.
- Estate and succession tax planning, including tax-efficient wills, estate freezes, and advice to taxable estates.
- Negotiating payment plans with the CRA to prevent bank account seizures, wage garnishments, and property liens, and filing taxpayer relief applications to cancel interest and penalties.
- International tax guidance for businesses operating across borders or establishing operations in Canada.
Our services are tailored to the unique circumstances of each taxpayer.
What Sets Us Apart
- Boutique Focus: We specialize exclusively in Canadian tax law, protecting taxpayers’ rights and resolving complex tax matters with precision.
- Strategic Advocates: We are not just advisors; we defend taxpayers in disputes with the tax authorities.
- Clarity & Precision: We simplify complex tax matters and provide clear, actionable solutions.
- Proven Results: Strong record of successful resolutions, strategic planning outcomes, and protected client interests.
Our Team of Trusted Income Tax Lawyers
Experienced Tax Lawyers to solve all of your Tax issues
