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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Framework Graphic 1 – representing Counter Tax Litigators' integrated approach to client service, combining advanced systems and deep legal expertise to resolve high-stakes tax disputes.

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Insights

The Three Critical Inflection Points in CRA Challenges

The Three Critical Inflection Points in CRA Challenges

September 07, 2025 - Peter Aprile, Senior Counsel at Counter LLP, describes three inflection points that define how CRA challenges develop and are resolved. The framework reflects insights drawn from years of...

Mutual Fund Trust Disputes: When Form Without Execution Collapses

Mutual Fund Trust Disputes: When Form Without Execution Collapses

August 21, 2025 - Key Takeaways Benefit without cost invites scrutiny: Courts scrutinize tax structures that offer benefit without tradeoff, and when they find this gap, they side with the CRA and uphold the...

Surplus Cash and the Active Asset Test: Lessons from Ehresman

Surplus Cash and the Active Asset Test: Lessons from Ehresman

August 14, 2025 - Key Takeaways No inference of intent: Courts rejected the claim that surplus cash was earmarked for decommissioning in the absence of contemporaneous reserves, allocations, or disclosures. ...

Strategic Deferral of Departure Tax: Security, Liquidity, and Control

Strategic Deferral of Departure Tax: Security, Liquidity, and Control

August 11, 2025 - Key Insights at a Glance Deferral as strategy: Departure tax can be deferred without interest when acceptable security is posted, preserving liquidity during transition. Forms of security: CRA...

Transfer Pricing Disputes: How Forum Choice Alters Outcomes

Transfer Pricing Disputes: How Forum Choice Alters Outcomes

June 30, 2025 - Key Takeaways Forum defines outcomes: The taxpayer’s appeal was quashed without the merits ever being heard because the chosen forum lacked jurisdiction. Procedure equals substance: Courts...

Framing Gaps in SR&ED Disputes Shift Control to CRA

Framing Gaps in SR&ED Disputes Shift Control to CRA

June 05, 2025 - Key Takeaways Framing gap: The Tax Court accepted CRA’s framing because Vortex’s reply lacked engineering support and legal positioning. In other disputes, when claims were framed with qualified...

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