Law360 Canada (August 12, 2026, 12:34 PM EDT) --

Bradley Phillips

Estate trustees and beneficiaries can often be faced with estate disputes that include complex commercial issues. A litigation lawyer may be needed to assist clients through these thorny and complex issues. For example, what happens when a prudent estate freeze triggers an intense family fallout, resulting in oppression remedies, wrongful dismissal claims, or derivative actions? How should an executor manage the multifaceted responsibilities of serving as an officer or director of the deceased’s business, especially when facing allegations of mismanagement or delaying a sale, while also drawing compensation?

In the evolution of the law dealing with estate freezes, the courts have increasingly prioritized objective corporate propriety over a founding patriarch’s intent to maintain control. In the seminal decision of Naneff v. Con-Crete Holdings Ltd., [1995] O.J. No. 1377, the Court of Appeal for Ontario established that the expulsion of a child (in this case a son) from a family business may be oppressive as it pertains to that child's shareholding interests in the company — which shareholding arose from an estate freeze having been implemented. While the court did not go so far as to say the oppressive conduct should trigger a forced public sale of the ousted son's shares, it still compelled the patriarch to buy out the son's gifted shares at fair market value.

The Divisional Court extended this judicial intervention even further in Strauss v. Wright, 2017 ONSC 5789, upholding the total removal of a founding patriarch as an officer and director after he attempted unauthorized corporate withdrawals. By distinguishing Strauss from Naneff on the basis of fiduciary breaches, the court effectively overlooked the patriarch's foundational right to control the business he built from his own bounty. Ultimately, these contrasting outcomes demonstrate that the court's subjective perception of corporate maneuvering appears to heavily dictate the scope of the broad oppression remedy.

Estate disputes might similarly require a host of sophisticated commercial issues that require intervention — sometimes urgently. Perhaps the estate is bound by complex contractual obligations, forcing the executor to perform or repudiate buy-sell provisions or debt obligations while guarding against personal liability. What about parallel estate disputes that throw an executor’s authority into doubt, jeopardizing time-sensitive mortgage renewals and risking power of sale proceedings? What if there is suspected misconduct by trustees or beneficiaries, necessitating extraordinary, without-notice remedies like Norwich or Anton Piller orders to locate or preserve critical evidence? When does it make sense to pursue a Certificate of Pending Litigation (CPL) in a real property dispute against alternative strategies to deter asset encumbrance?

The statutory context also shifts dramatically when an estate is insolvent. Here, standard collection methods fail, and creditors are forced into the orderly debt-compromise framework of the Bankruptcy and Insolvency Act. Practitioners must nimbly navigate statutory priority schemes, prove claims, or aggressively prosecute civil actions to challenge fraudulent conveyances and transfers at undervalue.

What makes these commercial/estate issues challenging is that they are highly context-specific and demand multi-layered legal strategies. Achieving competency in this complex field is not just about studying the case law; there are practical, strategic steps that experienced professionals can share. It is for this reason that Wagner Sidlofsky LLP is presenting a seven-part Zoom series of complimentary lunch and learn CLE seminars titled, "Profit, Power and Probate: Commercial Litigation in Estate Disputes" to explore the intersection of commercial and estate litigation.

Featuring leading professionals, including, Craig Vander Zee, Greg Sidlofsky, Clare Burns, Brad Phillips, Peter Neufeld and Ian Hull, as well as a host of other lawyers and professionals with extensive experience in these fields, this multi-part series will deliver practical guidance on corporate family disputes, executor liability, mortgage litigation, and insolvency remedies. Each session can be used towards substantive and professional CLE credits. There is no fee for the sessions, but we encourage you to donate generously to our selected charitable organizations in lieu of any fees. For more information and to register, please visit here.

Bradley Phillips is a partner and a member of Wagner Sidlofsky LLP’s estate and commercial litigation groups.

The opinions expressed are those of the author(s) and do not necessarily reflect the views of the author’s firm, its clients, LexisNexis Canada, Law360 Canada or any of its or their respective affiliates. This article is for general information purposes and is not intended to be and should not be taken as legal advice.

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