Holly Victoria Ashley Cunliffe

Holly focuses her practice on estate, trust and mental capacity litigation. She is known for delivering practical, results-driven solutions in matters that are often highly personal and emotionally challenging.

Holly is a member of the firm’s Tax and Trusts & Estates Groups, and Co-Leader of the Estate Litigation Group. She has extensive experience representing executors, trustees, beneficiaries, attorneys, guardians and concerned family members. Holly provides legal counsel on a wide variety of matters related to inheritance, power of attorney and guardianship. Additionally, she represents clients in complex litigation where an estate or trust is involved, including oppression proceedings in closely held family businesses. Holly frequently advises on legal issues such as will challenges, gift disputes, will and trust interpretation issues, passing of accounts, dependent support proceedings, mental capacity disputes, guardianship appointments, executor or trustee removals, complex estate and trust administration disputes, defending both trustee and executor conduct, will and trust variations and applications for advice and direction of the court.

Holly is a recognized leader in her field. She is a licensed Trust and Estate Practitioner (TEP) with the Society of Trust and Estate Practitioners (STEP). Holly is currently one of only 12 elected STEP worldwide members who form the steering committee for the global Mental Capacity Special Interest Group, staying at the forefront of mental capacity issues that affect succession planning and inheritance matters. Holly was an Executive Committee Member of the Ontario Bar Association’s Elder Law Section from 2019-2025 and an Executive Committee Member of the Trusts & Estates Section from 2021-2022.

"Understanding Capacity and Managing Our Own Emotions," STEP Atlantic Seminar, March 26, 2026.