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.

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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

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 Reassessments Behave Like Capital Events

CRA Reassessments Behave Like Capital Events

November 24, 2025 - Key Takeaways CRA’s incentive design produces earlier, larger, and more persistent reassessments. The Large Corporation Rules convert those assertions into temporary capital constraints. For...

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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