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Recognized as one of Canada's Top Tax Law Boutiques.

         
  • Free Consultation
  • Tax Services
    • Voluntary Disclosure
    • Audit
    • Objection
    • Tax Court of Canada
    • Cryptocurrency
    • Unfiled Returns
    • Tax Debt
    • Taxpayer Relief
    • Residency
    • More Services
      • Disability Tax Credit
      • Avoiding Bankruptcy
      • Criminal Defence
      • Judicial Review
      • Rectification
      • Remission Orders
      • Tax Planning
      • Business Advisory
  • Corporate Services
    • Acquisitions
    • Business Formation
    • Commercial and Residential Leasing
    • Commercial Contract Drafting and Review
    • Commercial Financing
    • Corporate Law and Record Maintenance
    • Corporate Reorganizations
    • Mergers
  • Our Firm
    • Our Team
    • About Us
    • Results
    • Decisions
    • Testimonials
    • Careers
      • Student Committee
  • Tax Law Blog
  • Contact Us
logologo
  • Free Consultation
  • Tax Services
    • Voluntary Disclosure
    • Audit
    • Objection
    • Tax Court of Canada
    • Cryptocurrency
    • Unfiled Returns
    • Tax Debt
    • Taxpayer Relief
    • Residency
    • More Services
      • Disability Tax Credit
      • Avoiding Bankruptcy
      • Criminal Defence
      • Judicial Review
      • Rectification
      • Remission Orders
      • Tax Planning
      • Business Advisory
  • Corporate Services
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Leading Canadian Tax Lawyers

Legal Team

James Pendergast VCARD

James Pendergast

Position:
Senior Managing Associate
Email:
james@rosentaxlaw.com
Phone:
(416) 593-4357

Personal Experience

James Pendergast is a Senior Managing Associate Lawyer at Rosen and Associates Tax Law.

At R&A Tax Law, James assists clients with the Canada Revenue Agency’s administrative appeals process and through litigation before the Tax Court of Canada and Federal Court. He has worked on matters including complex audits, appeals, real estate dispositions, cryptocurrency, small business tax issues, tax shelter structures, and indigenous taxation issues amongst various others.

James is our trusted Senior Managing Associate and commenced his legal career with R & A Tax Law as a Summer Student (19), returned as an Articling Student (20), and following his callto the Bar in Ontario (21) as an Associate.

James has been the Director of Student Development at R & A Tax Law since 2023 and has been the inaugural Director of the firm’s Health and Wellness Committee since January of 2025. His passions for fitness, mental health and wellness and employee wellbeing have underscored his coordination of firm yoga classes and fitness-oriented team events such as firm rock climbing and spin classes.

James was conferred his Juris Doctor degree University of Toronto Faculty of Law in June of 2020. During his legal education, James was a chair of the Faculty of Law’s Health and Wellness Committee, volunteered with the Law in Action Within Schools (LAWS) program and was an Associate Editor with the University of Toronto Law Review. In 2019, James competed for the University of Toronto at the 2019 Donald G. H. Bowman National Tax Moot and helped the 2020 team. James attended the School of Law at Trinity College Dublin in Dublin, Ireland for the fall semester of his final year of law school.

Prior to attending University of Toronto, James majored in Spanish at Dalhousie University and studied on exchange at Universidad Autónoma de Campeche in Campeche, Mexico. At Dalhousie, James was awarded the President’s Scholarship for outstanding academic achievement and graduated with Distinction.

James was raised on Prince Edward Island before moving to Nova Scotia for university. He grew up playing basketball, volleyball, tennis and running track and field. When not at work, he enjoys anything active, cooking and travelling.

Media

US Tax Rule Offers Template for Canadian Conservatives’ Investment Pitch (Bloomberg)

US Tax Rule Offers Template for Canadian Conservatives’ Investment Pitch (Financial Post)

Can Income from Off-Reserve Employment Be Tax-Exempt?

Recent Decisions

Xu v. HMK, 2021-1015(GST)APP – Tax Court of Canada (incorrect decision regarding GST/HST)

Bukhari v HMK, 2021-1705(IT)I

Bukhari v HMK, 2021-1706(IT)I

Kilpatrick v HMK, 2021-2502(IT)I

Knaff v HMK, 2020-1016(IT)I

Behnke v HMK 2021-1061(IT)G

Broderick v HMK 2021-860(IT)G

Coward v HMK 2021-871(IT)G

Velasquez v HMK 2020-1000(IT)G

Ord v HMK 2020-1604(IT)G

Greenham v HMK 2020-2066(IT)G

Kares v HMK 2020-453(IT)G

O’Hara v HMK 2020-481(IT)G

The Estate of the Late Wilfredo Farias v HMK 2020-540(IT)G

Roth v HMK 2020-963(IT)G

Bradley v HMK 2020-978(IT)G

Rajendram v. HMQ, 2020-267(GST)I – Tax Court of Canada (Settlement completed, Taxpayer entitled to New Home Housing Rebate)

McLean v. HMQ, 2020-630(IT)I – Tax Court of Canada (Settlement to allow all foreign tax credits claimed)

6478620 Canada Inc. v. HMK, 2020-409(IT)G

ASIF v. HMK, 2020-538(IT)G

Verrelli v. HMK, 2019-594(IT)G

Ghosh v HMK, 2019-3260(IT)G

Hsu v HMQ, 2019-1334(IT)G

Don’t Forget Me Doggies Inc. v HMK, 2019-3261(IT)G

Rutledge v. HMQ, 2018-3388(IT)G – Tax Court of Canada (Section 160 assessment vacated following settlement with the Department of Justice)

Mong, Tung Le v HMK, 2017-5072(IT)G

Dhingra v. HMK, 2017-3794(IT)I – Tax Court of Canada (Reducing taxpayer income)

Idone v HMK, 2015-2699(IT)G

Maconachie v A.G.C., T-1430-21 – Federal Court (Through settlement with the Department of Justice, the Applicant’s judicial review request was sent back to the CRA for a fresh review)

Wilfredo v MNR., T-113-21 – Federal Court (RRSP over-contribution penalty removed through a settlement with the Department of Justice)

Blog Posts

Missing Deadlines in Tax Disputes: Why Procedure Still Matters

Missing Deadlines in Tax Disputes: Why Procedure Still Matters

Background and Procedural History A recent decision from the Federal Court of Appeal serves as a strong reminder that, in tax disputes, procedure can be...

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Reopening Statute-Barred Tax Years: Lessons from Marleau v. The King

Reopening Statute-Barred Tax Years: Lessons from Marleau v. The King

Overview of the Decision The recent Tax Court of Canada decision in Marleau v. The King explains when the Canada Revenue Agency (“CRA”) can go back and...

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Bare Trusts in Real Estate: When to Use Them and How They Affect Taxation

Bare Trusts in Real Estate: When to Use Them and How They Affect Taxation

Bare trusts can be a useful tool in real estate transactions for privacy and tax neutrality, yet they are often misunderstood or overlooked. Like all tax...

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Understanding Requirements to Pay

Understanding Requirements to Pay

Being on the receiving end of legal action from the Canada Revenue Agency (“CRA”) can be incredibly stressful. Taxpayers who receive a “Requirement To Pay”...

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Navigating Properties with CRA Liens: What Sellers Need to Know

Navigating Properties with CRA Liens: What Sellers Need to Know

Selling a property already comes with many stresses and complexities, but when the CRA places a lien on the property, those complexities increase. Whether...

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When Is the Sale of Your Home Taxed as Business Income in Canada?

When Is the Sale of Your Home Taxed as Business Income in Canada?

Buying a home is often one of the largest investments a Canadian taxpayer will make. What many homeowners do not realize, however, is that selling a...

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How Tax Lawyers Help Navigate Complex Tax Controversies

How Tax Lawyers Help Navigate Complex Tax Controversies

When the Canada Revenue Agency (“CRA”) challenges a taxpayer filings or issues a reassessment, the resulting dispute can be both stressful and financially...

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The Hidden Evidence that Wins Tax Court Appeals: Third-Party Records

The Hidden Evidence that Wins Tax Court Appeals: Third-Party Records

Many taxpayers believe that once the Canada Revenue Agency “CRA” obtains third-party records, the outcome of an audit is inevitable. In reality, those...

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Tax Controversy in GST/HST Audits and Disputes

Tax Controversy in GST/HST Audits and Disputes

The Goods and Services Tax (“GST”) and Harmonized Sales Tax (“HST”) systems play a central role in Canada indirect tax regime. While designed to be self...

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The Burden of Proof in CRA Disputes: What Taxpayers Must Show

The Burden of Proof in CRA Disputes: What Taxpayers Must Show

One of the most common misconceptions amongst taxpayers involved in disputes with the Canada Revenue Agency (“CRA”) concerns who bears the burden of proof....

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