Estate disputes often extend far beyond questions of who inherits what. When a deceased person holds assets through corporate and/or trust structures, estate administration can become intertwined with corporate governance, tax planning, employment issues, business valuation, and litigation strategy.

The recent decision in Staples et al. v. Jean et al., 2024 ONSC 4590, aff’d 2026 ONCA 369 provides an instructive example of the challenges that can arise in administering such estates, and the need for a coordinated legal strategy across practice areas that addresses the full range of issues presented. Miller Thomson acted for the estate trustee in this litigation.

The litigation: How one estate required five areas of legal expertise

The deceased’s assets were held in a sophisticated structure that included interests in a holding company with shares owned by the deceased personally and through a family trust, as well as a profitable operating company.  

While the most valuable assets were held by the family trust, the administration of the estate quickly became the subject of significant litigation among family members. What started as a dispute over an estate trustee’s conduct soon required input across multiple disciplines: tax counsel to address a looming terminal tax liability, accountants to manage a loss carryback strategy and ongoing corporate bookkeeping, corporate counsel to navigate governance of the operating company, and employment counsel to address compensation claims raised by an employee who was also a beneficiary.

The applicants sought the removal of the estate trustee and took the position that her interpretation of the hotchpot clause in the deceased’s wills was incorrect. The court declined to remove the estate trustee, emphasizing the high threshold that must be met before a court will interfere with a testator’s choice of executor, and affirmed her interpretation of the hotchpot clause (rejecting the applicants’ interpretation).

The court found that the estate trustee had taken meaningful steps to administer the estate, address tax liabilities, preserve corporate assets, obtain professional advice, and advance the administration despite significant family conflict. In reaching its decision, the court specifically credited the estate trustee’s reliance on legal counsel and accountants as evidence of diligence rather than as an improper delegation of responsibility, a meaningful signal for trustees managing similarly multi-faceted estates.[1]

The applicants’ appeal of the lower court’s decision was ultimately dismissed with costs.

The broader lesson for estate trustees: Why complex estates cannot be administered in silos

While Staples involved unique facts, the issues encountered in the litigation are increasingly common. Many business owners now structure their affairs through holding companies, trusts, and other sophisticated structures that create legal questions extending well beyond traditional estate administration.

Estate Trustees in these circumstances may find themselves addressing, often simultaneously:

  • estate administration;
  • will interpretation;
  • corporate governance issues;
  • business succession planning;
  • employment matters;
  • tax planning and compliance; and
  • litigation strategy.

Questions that initially appear to be straightforward estate issues may ultimately require solutions that consider multiple areas of law. Decisions regarding whether to continue operating a business, distribute shares, resolve employment claims, or address shareholder concerns may all be raised in the estate administration context.

For estate trustees, the principal takeaway is the importance of obtaining coordinated legal advice that reflects the full scope of the issues at play. Complex estates are rarely administered in silos. Rather, they require strategic guidance that considers the interaction between multiple areas of law and the practical realities of managing both an estate and the business interests connected to it.

A comprehensive and multidisciplinary approach can be critical to advising estate trustees on how to navigate their obligations, manage risk, preserve value, and advance the administration of complex estates in an efficient and effective manner. Estate trustees may wish to consider full-service legal representation to assist them in navigating their various responsibilities where legal assistance is required.

If you are a trustee or estate solicitor managing complex assets in circumstances where litigation is underway or on the horizon, Miller Thomson’s Estates and Trusts Litigation lawyers can help you coordinate the full range of expertise these matters often require.

[1] It is important, however, to carefully consider each case on its own facts before professionals are retained across various disciplines.