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David J. Rotfleisch

David J. Rotfleisch

  • Firm: Taxpage
Email:
  • 2822 Danforth Avenue, Toronto, Ontario M4C 1M1.
Taxpage

David J. Rotfleisch is one of Canada’s most experienced and credentialed tax lawyers, bringing over 35 years of tax litigation, planning, and dispute-resolution expertise to clients across the country. He is a founding Canadian tax lawyer and one of only 16 Ontario Certified Specialists in Taxation as of 2026. A rare dual-qualified professional, he is both a lawyer and a Chartered Professional Accountant and has completed the esteemed CICA In-Depth Tax Course, allowing him to blend legal strategy with accounting precision.

David’s practice spans the full spectrum of Canadian income tax and cryptocurrency taxation. He advises Canadian taxpayers, start-ups, resident and non-resident business owners, corporations, and high-net-worth individuals on matters ranging from routine compliance to highly complex tax and estate planning. Over his extensive career, he has represented several clients in voluntary disclosures (VDP), tax audits, and every stage of tax dispute resolution and litigation.

With additional professional experience in the computer and IT industry, David brings technical insight into blockchain systems, smart contracts, crypto business models, and the legal challenges of emerging technologies. This combination of deep tax proficiency and digital-asset expertise uniquely positions him to advise innovation-driven businesses operating across both traditional and digital economies.

Specializations

  • Tax Law
  • Corporate & Business Law
  • Estate & Succession Planning
  • Real Estate Taxation
  • Crypto Taxation
  • International/Offshore Tax Compliance

Education

  • J.D., Osgoode Hall Law School
  • B.Com., McGill University 

Membership

  • Canadian bar association {CBA}
  • Law Society of Ontario
  • Chartered Professional Accountant {CPA} (Lifetime Member), Canada.

Public Speaking

  • Canadian Bar Association webinar series – Estate Planning in the Modern Era for Crypto Assets – November 2023
  • Certified Professional Bookkeepers of Canada (CPB Canada) – “Autumn Tax Primer” program – November 2024

Publications

“Canadian Tax Facts” is a comprehensive global resource for reporters, editors, TV and radio producers, and anyone interested in business and personal tax rates, tax audits, reassessments, cryptocurrency taxation, and issues related to tax evasion, unreported offshore income, and Black Money.

Published Articles

  • Binance’s Exit From Ontario Amid Regulatory Action By OSC, 12 July, 2021.
  • Canadian Income Tax Implications Of Buying & Selling Blockchain NFTs, 27 April, 2021.
  • TFSA Tax: Canadian Tax Lawyer Guidance, 25 August, 2021.
  • Employee Stock Options Tax Treatment: Canadian Tax Lawyer’s Guide, 2 June,, 2021.
  • Binance’s Exit From Ontario Amid Regulatory Action By OSC, 12 July 2021.
  • The Canadian Income Tax And Cryptocurrency Staking: Knowing The Income-Tax Consequences For Canadians In The Validation Of Cryptocurrency Transactions In Proof-Of-Stake Blockchain, 8 December, 2022.
  • Everything You Need To Know About The Underused Housing Tax (2022), On Vacant Or Underused Housing In Canada, 10 March, 2023.
  • Canadian Tax Treatment Of Roth Individual Retirement Arrangement (Roth IRA), 7 July, 2022.
  • Binance Bids Canada Bye-Bye! Canadian Tax Implications For Cryptocurrency Investors And Traders, 9 June, 2023.
  • How To Legitimately Defer The Worst Of Canada’s ‘Departure Tax’ When Becoming A Non-Resident And Moving To Another Country, 23 June, 2023.
  • How To Claim a Tax Loss & Tax Deductions for Victims Of ‘Pig Butchering’ Fake Crypto Investment Scams Tip: Tips from a Canadian Tax Lawyer, 29 April, 2024.
  • A Comprehensive Guide to Tax for Canadian Property Owners, Investors In Canadian Property Part III: Tax Obligations for Long-Term and Short-Term Rentals, 9 September, 2024.
  • Year-End Tax Planning For Tax-Free Savings Accounts: Top TFSA Moves You Should Make Before The End Of 2024, 22 November, 2024.
  • FINTRAC And CRA Team Up To Combat Money Laundering The Proceeds Of Tax Evasion Using Real Estate, 9 January 2025.
  • Case Commentary: 1351231 Ontario Inc. v The King – Why GST/HST Must Be Paid On The Sale Of A Residential Unit Used For Airbnb, 7 April, 2025.
  • The CRA Issues A New ‘Income Tax Folio’ On How Shareholder Loans And Debts Are Treated, 5 August, 2025.
  • How Are Professional Poker Winnings Taxed In Canada? Taxable Business Income And Non-Taxable Hobbies: Fournier-Giguère V. Canada Et. Al., 2025 FCA 112, 15 July, 2025.
  • Canada Revenue Agency Tightens Oversight On Cryptocurrency Transactions: What You Need To Know Now, 7 May, 2025.
  • Canadian Tax Traps For Professional Athletes Entering, Leaving, Or Playing In Canada: Tax-Planning Considerations For Cross-Border Professional Athletes, 6 November 2024.

Awards / Achievement

  • Mondaq ‘Thought Leadership Awards,’ Autumn 2021 – Fin Tech & Intellectual Property
  • Mondaq ‘Thought Leadership Awards,’ Spring 2022 – Finance and Banking & Employment and HR
  • Mondaq ‘Thought Leadership Awards,’ Autumn 2022 – Fin Tech
  • Mondaq ‘Thought Leadership Awards,’ Spring 2023 – Fin Tech, Employment and HR & Real Estate and Construction
  • Mondaq ‘Thought Leadership Awards,’ Autumn 2023 – Fin Tech & Technology
  • Mondaq ‘Thought Leadership Awards,’ Spring 2024 – Immigration
  • Mondaq ‘Thought Leadership Awards,’ Autumn 2024 – Fin Tech
  • Mondaq ‘Thought Leadership Awards,’ Spring 2025 – Real Estate and Construction, Finance and Banking & Government, Public Sector
  • Mondaq ‘Thought Leadership Awards,’ Autumn 2025 – Real Estate and Construction, Finance and Banking, Media, telecoms, IT, Entertainment, Fin Tech & Employment and   HR
  • FeedSpot Award – “Best 25 Tax Lawyer Blogs” – June 2023
  • FeedSpot Award – “60 Best Canadian Tax Blogs and Websites” – November 2023
  • FeedSpot Award – Best Canadian Tax Blogs & Websites – May 2025
  • FeedSpot Award – Best Tax Blog in Canada – September 2025

Media Appearance

  • BNN Bloomberg, Television Interview – “CERB Repayments,” Television Interview, December 10, 2020.
  • CityNews, Video News Feature – “CERB Repayments,” December 13, 2020.
  • BNN Bloomberg, Online Video Interview – “Tax Tips, April 16, 2021.
  • BNN Bloomberg, Online Video Interview – “Tax-Related Questions,” December 16, 2021.
  • BNN Bloomberg, Online Video Interview – “Cryptocurrency Taxation,” December 16, 2021.
  • Zoomer Radio, Radio Interview – “Calls on the Government to Extend the Tax Deadline,” April 26, 2021.
  • Zoomer Radio – Fight Back with Libby Znaimer, Radio Interview – “Property Taxes Amid the Pandemic,” March 23, 2022.
  • CBC Radio, Radio Interview with Amanda Pfeffer – “Impact of Federal Employee Strike on Tax Season 2023,” April 24, 2023.
  • CBC – About That, YouTube Video Interview with Andrew Chang, – “Who’s Telling the Truth About the Capital Gains Tax?” June 14, 2024.
  • CBC – About That, YouTube Video Interview with Andrew Chang – “How Do Carney and Poilievre’s Income Tax Cuts Compare?”, March 26, 2025.
  • Zoomer Radio – Fight Back with Libby Znaimer, Radio Interview, – “TurboTax Users Hit with Surprise CRA Bills Over Credit Errors,” April 16, 2025.
  • Zoomer Radio – Fight Back with Libby Znaimer, Radio Interview, Toronto, Ontario, – “Why Are Canadian Retirees Hit So Hard by Taxes?” November 5, 2025.

Other Websites

These websites provide additional insight into the breadth of David’s expertise and the specialized services offered by his team, both in Canada and internationally.

Taxlawyer.com – For cross-border and U.S.-Canada tax matters, including IRS audits, IRS voluntary disclosure programs, CRA audits, crypto taxation, payroll and sales taxes, offshore income reporting, and unfiled taxes.

Crypto Taxlawyer – Specialized cryptocurrency taxation guidance, including crypto tax audits, planning, defence, voluntary disclosures, unfiled crypto taxes, and offshore crypto income.

Canadian Tax Amnesty – For more information on voluntary disclosures, unfiled taxes, CRA audits, and tax prosecution. It also covers guidance on unreported offshore income and a comprehensive guide to CRA taxation in Canada.

Goods Service Tax – For Canadians facing GST or HST issues, assessments, or collections. This site provides expert legal support to fight the CRA and protect taxpayer rights.

Tax Law Canada – Covers Canadian tax matters, including income tax planning, tax disputes, corporate and family tax planning, CRA collections, tax evasion and fraud, and foreign income compliance.

David J. Rotfleisch is one of Canada’s most experienced and credentialed tax lawyers, bringing over 35 years of tax litigation, planning, and dispute-resolution expertise to clients across the country. He is a founding Canadian tax lawyer and one of only 16 Ontario Certified Specialists in Taxation as of 2026. A rare dual-qualified professional, he is both a lawyer and a Chartered Professional Accountant and has completed the esteemed CICA In-Depth Tax Course, allowing him to blend legal strategy with accounting precision.

David’s practice spans the full spectrum of Canadian income tax and cryptocurrency taxation. He advises Canadian taxpayers, start-ups, resident and non-resident business owners, corporations, and high-net-worth individuals on matters ranging from routine compliance to highly complex tax and estate planning. Over his extensive career, he has represented several clients in voluntary disclosures (VDP), tax audits, and every stage of tax dispute resolution and litigation.

With additional professional experience in the computer and IT industry, David brings technical insight into blockchain systems, smart contracts, crypto business models, and the legal challenges of emerging technologies. This combination of deep tax proficiency and digital-asset expertise uniquely positions him to advise innovation-driven businesses operating across both traditional and digital economies.

Specializations

  • Tax Law
  • Corporate & Business Law
  • Estate & Succession Planning
  • Real Estate Taxation
  • Crypto Taxation
  • International/Offshore Tax Compliance

Education

  • J.D., Osgoode Hall Law School
  • B.Com., McGill University 

Membership

  • Canadian bar association {CBA}
  • Law Society of Ontario
  • Chartered Professional Accountant {CPA} (Lifetime Member), Canada.

Public Speaking

  • Canadian Bar Association webinar series – Estate Planning in the Modern Era for Crypto Assets – November 2023
  • Certified Professional Bookkeepers of Canada (CPB Canada) – “Autumn Tax Primer” program – November 2024

Publications

“Canadian Tax Facts” is a comprehensive global resource for reporters, editors, TV and radio producers, and anyone interested in business and personal tax rates, tax audits, reassessments, cryptocurrency taxation, and issues related to tax evasion, unreported offshore income, and Black Money.

  • Canadian Tax Facts 2022 – https://taxpage.com/wp-content/uploads/2022/04/Canadian-Tax-Facts-2022-David-Rotfleisch-Taxpage.pdf – 1st edition
  • Canadian Tax Facts 2023- https://taxpage.com/wp-content/uploads/2023/04/TAXPAGE-Tax-Facts-2023.pdf – 2nd edition
  • Canadian Tax Facts 2024 – https://taxpage.com/wp-content/uploads/2024/04/TaxPage-Tax-Facts-2024.pdf – 3rd edition
  • Canadian Tax Facts 2025 – https://taxpage.com/wp-content/uploads/2025/04/TaxPage-Tax-Facts-2025.pdf – 4th edition

Published Articles

  • Binance’s Exit From Ontario Amid Regulatory Action By OSC, 12 July, 2021.
  • Canadian Income Tax Implications Of Buying & Selling Blockchain NFTs, 27 April, 2021.
  • TFSA Tax: Canadian Tax Lawyer Guidance, 25 August, 2021.
  • Employee Stock Options Tax Treatment: Canadian Tax Lawyer’s Guide, 2 June,, 2021.
  • Binance’s Exit From Ontario Amid Regulatory Action By OSC, 12 July 2021.
  • The Canadian Income Tax And Cryptocurrency Staking: Knowing The Income-Tax Consequences For Canadians In The Validation Of Cryptocurrency Transactions In Proof-Of-Stake Blockchain, 8 December, 2022.
  • Everything You Need To Know About The Underused Housing Tax (2022), On Vacant Or Underused Housing In Canada, 10 March, 2023.
  • Canadian Tax Treatment Of Roth Individual Retirement Arrangement (Roth IRA), 7 July, 2022.
    Binance Bids Canada Bye-Bye! Canadian Tax Implications For Cryptocurrency Investors And Traders, 9 June, 2023.
  • How To Legitimately Defer The Worst Of Canada’s ‘Departure Tax’ When Becoming A Non-Resident And Moving To Another Country, 23 June, 2023.
  • How To Claim a Tax Loss & Tax Deductions for Victims Of ‘Pig Butchering’ Fake Crypto Investment Scams Tip: Tips from a Canadian Tax Lawyer, 29 April, 2024.
  • A Comprehensive Guide to Tax for Canadian Property Owners, Investors In Canadian Property Part III: Tax Obligations for Long-Term and Short-Term Rentals, 9 September, 2024.
  • Year-End Tax Planning For Tax-Free Savings Accounts: Top TFSA Moves You Should Make Before The End Of 2024, 22 November, 2024.
  • FINTRAC And CRA Team Up To Combat Money Laundering The Proceeds Of Tax Evasion Using Real Estate, 9 January 2025.
  • Case Commentary: 1351231 Ontario Inc. v The King – Why GST/HST Must Be Paid On The Sale Of A Residential Unit Used For Airbnb, 7 April, 2025.
  • The CRA Issues A New ‘Income Tax Folio’ On How Shareholder Loans And Debts Are Treated, 5 August, 2025.
  • How Are Professional Poker Winnings Taxed In Canada? Taxable Business Income And Non-Taxable Hobbies: Fournier-Giguère V. Canada Et. Al., 2025 FCA 112, 15 July, 2025.
  • Canada Revenue Agency Tightens Oversight On Cryptocurrency Transactions: What You Need To Know Now, 7 May, 2025.
  • Canadian Tax Traps For Professional Athletes Entering, Leaving, Or Playing In Canada: Tax-Planning Considerations For Cross-Border Professional Athletes, 6 November 2024.

Awards / Achievement

  • Mondaq ‘Thought Leadership Awards,’ Autumn 2021 – Fin Tech & Intellectual Property
  • Mondaq ‘Thought Leadership Awards,’ Spring 2022 – Finance and Banking & Employment and HR
  • Mondaq ‘Thought Leadership Awards,’ Autumn 2022 – Fin Tech
  • Mondaq ‘Thought Leadership Awards,’ Spring 2023 – Fin Tech, Employment and HR & Real Estate and Construction
  • Mondaq ‘Thought Leadership Awards,’ Autumn 2023 – Fin Tech & Technology
  • Mondaq ‘Thought Leadership Awards,’ Spring 2024 – Immigration
  • Mondaq ‘Thought Leadership Awards,’ Autumn 2024 – Fin Tech
  • Mondaq ‘Thought Leadership Awards,’ Spring 2025 – Real Estate and Construction, Finance and Banking & Government, Public Sector
  • Mondaq ‘Thought Leadership Awards,’ Autumn 2025 – Real Estate and Construction, Finance and Banking, Media, telecoms, IT, Entertainment, Fin Tech & Employment and   HR
  • FeedSpot Award – “Best 25 Tax Lawyer Blogs” – June 2023
  • FeedSpot Award – “60 Best Canadian Tax Blogs and Websites” – November 2023
  • FeedSpot Award – Best Canadian Tax Blogs & Websites – May 2025
  • FeedSpot Award – Best Tax Blog in Canada – September 2025

Media Appearance

  • BNN Bloomberg, Television Interview – “CERB Repayments,” Television Interview, December 10, 2020.
  • CityNews, Video News Feature – “CERB Repayments,” December 13, 2020.
  • BNN Bloomberg, Online Video Interview – “Tax Tips, April 16, 2021.
  • BNN Bloomberg, Online Video Interview – “Tax-Related Questions,” December 16, 2021.
  • BNN Bloomberg, Online Video Interview – “Cryptocurrency Taxation,” December 16, 2021.
  • Zoomer Radio, Radio Interview – “Calls on the Government to Extend the Tax Deadline,” April 26, 2021.
  • Zoomer Radio – Fight Back with Libby Znaimer, Radio Interview – “Property Taxes Amid the Pandemic,” March 23, 2022.
  • CBC Radio, Radio Interview with Amanda Pfeffer – “Impact of Federal Employee Strike on Tax Season 2023,” April 24, 2023.
  • CBC – About That, YouTube Video Interview with Andrew Chang, – “Who’s Telling the Truth About the Capital Gains Tax?” June 14, 2024.
  • CBC – About That, YouTube Video Interview with Andrew Chang – “How Do Carney and Poilievre’s Income Tax Cuts Compare?”, March 26, 2025.
  • Zoomer Radio – Fight Back with Libby Znaimer, Radio Interview, – “TurboTax Users Hit with Surprise CRA Bills Over Credit Errors,” April 16, 2025.
  • Zoomer Radio – Fight Back with Libby Znaimer, Radio Interview, Toronto, Ontario, – “Why Are Canadian Retirees Hit So Hard by Taxes?” November 5, 2025.

Other Websites

These websites provide additional insight into the breadth of David’s expertise and the specialized services offered by his team, both in Canada and internationally.

Taxlawyer.com – For cross-border and U.S.-Canada tax matters, including IRS audits, IRS voluntary disclosure programs, CRA audits, crypto taxation, payroll and sales taxes, offshore income reporting, and unfiled taxes.

Crypto Taxlawyer – Specialized cryptocurrency taxation guidance, including crypto tax audits, planning, defence, voluntary disclosures, unfiled crypto taxes, and offshore crypto income.

Canadian Tax Amnesty – For more information on voluntary disclosures, unfiled taxes, CRA audits, and tax prosecution. It also covers guidance on unreported offshore income and a comprehensive guide to CRA taxation in Canada.

Goods Service Tax – For Canadians facing GST or HST issues, assessments, or collections. This site provides expert legal support to fight the CRA and protect taxpayer rights.

Tax Law Canada – Covers Canadian tax matters, including income tax planning, tax disputes, corporate and family tax planning, CRA collections, tax evasion and fraud, and foreign income compliance.

FAQ about David J. Rotfleisch

David Rotfleisch has over 35 years of experience providing legal services to individuals, businesses, and international clients, with specialized expertise in Canadian income tax law, cryptocurrency taxation, tax planning, CRA tax audits, voluntary disclosures, tax dispute resolution, expert opinions for litigation, and technology-related tax matters. He is a Canadian tax lawyer, one of only 16 Ontario Certified Specialists in Taxation, a Chartered Professional Accountant, and a graduate of the CICA In-Depth Tax Course.

He primarily works in Canadian income tax law & crypto taxation, including tax planning, tax disputes, tax audits, GST/HST, voluntary disclosures, estate tax matters, and technology-related tax issues.

His key specialties include:

  • Tax Law
  • Corporate & Business Tax
  • GST/HST
  • Estate & Succession Planning
  • Cryptocurrency Taxation
  • International/Offshore Tax Compliance
  • High-tech and IT-related legal/tax matters

He currently practices in Toronto, Ontario, as the founding lawyer of Taxpage.com / Rotfleisch & Samulovitch P.C., a Canadian boutique tax law firm specializing in Canadian income tax, crypto taxation, voluntary disclosures, tax audits, and dispute resolution.

Yes. He provides legal services to non-residents, international businesses, offshore clients, and cross-border taxpayers on crypto taxation, Canadian tax compliance and planning.

You can find more information on Taxpage, legal directories, professional profiles like LinkedIn, or legal publications.

Q&A With David J. Rotfleisch

Global-Law-Experts-Q-And-A-Video-Coming-Soon

Education

Bachelor of Commerce Degree
  • McGill University
  • 1976
Juris Doctor (JD)
  • Osgoode Hall Law School
  • 1983

David J. Rotfleisch Latest Posts

David J. Rotfleisch Latest Videos

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