James Roberts and the Counter Tax Litigators team for their hands-on, strategic approach to tax dispute resolution.

James Roberts

Partner, Tax Litigation

James is a tax litigator powered by his desire to help companies expand and thrive.

James represents private companies and high-net-worth individuals in all aspects of tax litigation. He has appeared at the Tax Court of Canada and the Federal Courts.  

Some recent highlights in James’ tax litigation practice include the following: 

  • Successfully resolved a multi-million-dollar tax dispute for a privately owned and managed international company. James used a litigation strategy that led to a 94 per cent reduction of the disputed amount and yielded a significant litigation ROI.  
  • Met or surpassed the target outcome zone in all matters settled in 2022.  
  • Resolved a tax dispute about non-compliance with foreign reporting requirements, leading to a reduction of over $3M in penalties.  
  • Convinced the CRA to completely abandon its stance on the main intent of a substantial capital investment, saving the taxpayer more than $2M and several years of potential litigation. 
I’m a Senior VP who has previously hired large law firms. I was referred to Counter to fix a tax dispute from the sale of an investment property I co-owned with two non-residents. I wish I hired Counter sooner.

- David Cuddy, Senior Vice-President, Finance & Business Operations, CFL 

Natalie, James and Jennifer have been wonderful to work with for our numerous legal cases. They understand there’s a job to be done and they get it done with minimal fuss and detailed written follow-up.

- Verified Client Feedback for the Legal 500: 2024 Elite Tax Boutique Award

Counter delivered superior communication, high-quality submissions and a great result.

- Laura Couvrette, CPA, CA, Fuller Landau LLP 

James started his career at Counter Tax Litigators as a summer student in 2016. Since starting at Counter, James has earned his tax and litigation expertise. Leading tax publications publish his tax dispute insights, and he has helped some of Canada’s top private companies win their tax disputes.  

Outside of work, James enjoys spending time with his wife and child. He is also an avid sports fan.

Latest Insights

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The Strategic Choice After Reassessment

Comparing the CRA’s self-adjudication stage with independent oversight in appeal
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Insights

Loss Consolidation Under GAAR: When Interpretation and Judgement Decide the Outcome

Loss Consolidation Under GAAR: When Interpretation and Judgement Decide the Outcome

November 25, 2025 - Key Takeaways Loss consolidation transactions attract CRA scrutiny even when they align with Parliament’s design. The mechanical structure rarely drives the dispute – the interpretive record does.

How Courts Decide When a Transaction Can Be Read Two Ways

How Courts Decide When a Transaction Can Be Read Two Ways

November 24, 2025 - Key Takeaways Penn Ventilator v. HMQ shows how disputes evolve when a transaction supports two viable case theories: one tied to the structure, the other to the business’s economic behaviour. ...

Control and Economic Reality in Cross-Border Dividend Disputes

Control and Economic Reality in Cross-Border Dividend Disputes

November 24, 2025 - Key Takeaways Inconsistent cross-border descriptions created tension between the structure’s design and its economic reality. Risk and benefit flowed to different entities across jurisdictions,...

CRA Audits and Disputes: A New Test of Control and Judgement

CRA Audits and Disputes: A New Test of Control and Judgement

November 03, 2025 - Key Points CRA can now compel sworn questioning. The Income Tax Act authorizes auditors to require oral testimony under oath during audits, bringing executives directly into the record. Early...

When CRA Scrutiny Shifts from Mechanics to Interpretive Requirements

When CRA Scrutiny Shifts from Mechanics to Interpretive Requirements

October 29, 2025 - Key Takeaways CRA challenges often evolve from mechanical to interpretive tests. The decisive factor is not a structure’s mechanics but whether its interpretive elements hold up under scrutiny. ...

Foreign Tax Interest Denied, Tax Court Loss Contained — Bank of Montreal v. HMK

Foreign Tax Interest Denied, Tax Court Loss Contained — Bank of Montreal v. HMK

September 22, 2025 - Key Takeaways The Tax Court confirmed that foreign tax interest is not deductible — BMO lost on the law. The result was predictable, but BMO's strategy maximized potential upside while containing...

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