2025-03-18 - Bonnie Chiapponi Headshot

Bonnie Chiapponi

Operations Lead

Drives operational excellence to enhance tax litigation performance.

Bonnie leads strategic initiatives that optimize Counter Tax Litigators’ operations, ensuring efficiency, seamless execution, and alignment with the firm’s tax litigation strategy. Her work strengthens firm-wide processes, enabling lawyers to maintain focus on securing high-stakes litigation outcomes.

With a background in executive operations and process improvement, Bonnie ensures that Counter Tax Litigators’ infrastructure supports the demands of complex tax disputes. She specializes in streamlining workflows, integrating cross-functional initiatives, and reinforcing the systems that drive litigation performance.

This structured, execution-driven approach enhances Counter Tax Litigators’ ability to deliver precision, strategy, and successful tax litigation results.

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

Counter worked smart and hard to help us win the appeal. We worked together to reorganize all the evidence, and we presented a clear and coherent case. We won and avoided roughly $600,000 in tax, penalties, and interest.

- Fred Levy, CPA, CA, LPA, MBA

Simply the best is how I would describe Counter Tax. They were on top of everything that CRA and the MOF were throwing at us, and kept us informed and well-advised on next steps. By the way, they won both cases.

- John Locke, President, Campbellford Wholesale Inc.

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

When a Tax Court Appeal Becomes Cost, Not Opportunity

When a Tax Court Appeal Becomes Cost, Not Opportunity

February 06, 2026 - Key Takeaways The appeal failed because the parties continued after the win path had closed. The hearing created no real opportunity or upside. The case continued without a clear stop-point, turning...

Where an Interest Deduction Dispute Is Effectively Shaped

Where an Interest Deduction Dispute Is Effectively Shaped

February 06, 2026 - Keybrand Foods Inc. v. HMQ, shows how interest-deductibility disputes, and others like them, are shaped after reassessment as the objection record crystallizes the explanation of the business...

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.

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,...

Costs Follow Control, Not Optimism

Costs Follow Control, Not Optimism

November 20, 2025 - Key Takeaways Enhanced costs continue to rise. The Tax Court again imposed enhanced costs on the Crown, reinforcing a pattern: disciplined conduct in the right arena creates financial consequences...

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...

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