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Strategic Tax Planning in Light of Deans Knight: Navigating High-Net-Worth Family Business Taxation with Expertise and Foresight


The Supreme Court of Canada’s ruling in Deans Knight Income Corporation v. Her Majesty the Queen represents a landmark decision in the context of Canadian tax law, particularly relevant to high-net-worth individuals and family-owned enterprises. This decision meticulously analyzes the application of the General Anti-Avoidance Rule (GAAR) and distinguishes between legitimate tax planning and potential abuse of tax law provisions. As tax practitioners, grasping the subtleties of this ruling is crucial to avoid strategies that may be perceived as abusive tax avoidance.

Case Background

Deans Knight Income Corporation, initially involved in mineral exploration and later transitioning to pharmaceuticals, had accrued significant tax attributes due to consistent losses. Faced with potential insolvency, the company, under the advisement of PricewaterhouseCoopers, sought to leverage its non-capital losses, SRED, and ITCs. Matco Capital Ltd., a venture capital firm, devised a series of intricate transactions to realize this goal.

  • Deans Knight’s Initial Business Operations: Initially engaged in mineral exploration.
  • Transition to Pharmaceuticals: Deans Knight later shifted its focus to the pharmaceutical sector.
  • Accumulation of Tax Attributes: Due to consistent losses in its business operations, Deans Knight accumulated significant non-capital losses, Scientific Research and Experimental Development (SRED) credits, and Investment Tax Credits (ITCs).
  • Facing Financial Challenges: The company confronted potential insolvency and the risk of being delisted.
  • Engagement of PricewaterhouseCoopers: Deans Knight sought advice from PricewaterhouseCoopers to explore ways to utilize its tax attributes effectively.
  • Matco Capital Ltd.’s Involvement: Matco Capital Ltd., a venture capital firm, was engaged to facilitate the realization of value from Deans Knight’s tax attributes.
  • Strategic Plan Development: A strategy was developed involving the creation of a new entity (NewCo) and the use of Deans Knight’s remaining corporate structure.
  • Creation of NewCo: NewCo was established to house Deans Knight’s assets and liabilities.
  • Initial Public Offering (IPO): Deans Knight utilized its remaining corporate shell to raise funds through an IPO for a new business venture.
  • Objective of the Transactions: The aim was to leverage the Tax Attributes in the operations of the new business venture.
  • Design of Transactions to Avoid De Jure Control by Matco: The transactions were meticulously structured to prevent Matco from obtaining de jure control over Deans Knight.
  • Recapitalization and Business Restart: The transactions facilitated a recapitalization and restart of Deans Knight’s business operations.
  • Judicial Examination: The Supreme Court was tasked with evaluating whether the transactions led to an acquisition of control by Matco, which would affect Deans Knight’s ability to deduct the Tax Attributes, and whether the transactions were abusive under the GAAR.
  • Supreme Court’s Analysis and Decision: The Court analyzed the commercial reality and legal form of the transactions and their compliance with GAAR.

Transactional Complexity

The strategy entailed creating a new entity (NewCo) to house Deans Knight’s assets and liabilities, while using the remaining corporate shell to raise funds via an IPO for a new business venture, thereby utilizing the Tax Attributes. These transactions were intricately designed to avoid Matco acquiring de jure control, while enabling a recapitalization and business restart for Deans Knight.

Judicial Scrutiny

The Supreme Court focused on whether Matco’s involvement resulted in an acquisition of control, thereby impacting Deans Knight’s ability to deduct the Tax Attributes as per the tax attribute streaming restrictions. Furthermore, the Court scrutinized the applicability of GAAR, analyzing each transaction step to discern the commercial reality from its legal form.

Implications for Tax Planning

The ruling underscores the necessity for transparent and bona fide transactions in tax planning. For high-net-worth families and their businesses, this decision highlights the critical importance of ensuring that tax reorganizations reflect genuine business purposes, not merely avenues for tax avoidance.

Guidance for Future Strategies

Families and enterprises should engage in prudent tax planning, particularly when leveraging Tax Attributes. Collaboration with tax experts, including Chartered Professional Accountants (CPA, CA) and legal professionals with a Master in Tax Law (LL.M (Tax)), is vital to navigate potential risks associated with aggressive tax strategies.

Emphasis on Economic Substance

A key aspect of the Supreme Court’s judgment is the focus on substantive economic activities. The Court emphasized that these activities must reflect genuine business purposes, contributing meaningfully to the corporation’s economic fabric, beyond serving as mere vehicles for tax benefits. The Court examined whether Deans Knight’s transactions, including the creation of NewCo and the IPO, were aligned with bona fide business activities or constituted abusive tax avoidance under GAAR.

Economic Substance in Tax Planning

For high-net-worth families owning enterprises, this decision necessitates a thorough evaluation of tax strategies to ensure that any reorganization, especially those involving tax attributes, is underpinned by real economic substance. This means creating tangible business activities that extend beyond theoretical transactions typically associated with aggressive tax planning.

Closing Advisory

In light of the Deans Knight Income Corporation v. Her Majesty the Queen ruling, it is imperative for high-net-worth families and their advisors to approach tax reorganizations with caution. Tax strategies should be closely aligned with the substantive economic activities of the business, adhering to the spirit of tax law. As tax experts, our commitment is to guide you through these intricacies, ensuring your tax strategies are resilient, defensible, and aligned with your long-term objectives.


This information is for discussion purposes only and should not be considered professional advice. There is no guarantee or warrant of information on this site and it should be noted that rules and laws change regularly. You should consult a professional before considering implementing or taking any action based on information on this site. Call our team for a consultation before taking any action. ©2024 Shajani CPA.

Shajani CPA is a CPA Calgary, Edmonton and Red Deer firm and provides Accountant, Bookkeeping, Tax Advice and Tax Planning service

Nizam Shajani, Partner, LLM, CPA, CA, TEP, MBA

I enjoy formulating plans that help my clients meet their objectives. It's this sense of pride in service that facilitates client success which forms the culture of Shajani CPA.

Shajani Professional Accountants has offices in Calgary, Edmonton and Red Deer, Alberta. We’re here to support you in all of your personal and business tax and other accounting needs.