Holly V.A. Cunliffe TEP
Admitted to the Ontario Bar: 2014
-
Toronto
- Bio
- Awards & Recognition
- Professional Involvement
- Representative Matters
- Selected Speaking Engagements
- Selected Publications
- Insights
- Education
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 Estates & Trusts Groups. 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.
Awards & Recognition
- Recognized in The Canadian Legal Lexpert Directory as a leading individual in Estate Litigation
- Recognized in The Best Lawyers in Canada in Trusts and Estates
- Recognized as an Up & Coming Partner in Chambers HNW: The World's Leading High Net Worth Advisers for her expertise in Private Wealth Disputes (Canada)
Professional Involvement
Memberships:
- Mental Capacity Global SIG Steering Committee, The Society of Trust and Estate Practitioners, 2020-present
- Elder Law Section Executive, Ontario Bar Association, 2019-2025
- Executive Committee Member, Trusts & Estates Section, Ontario Bar Association, 2021-2022
- Canadian Bar Association
- Ontario Bar Association
- The Advocates' Society
Representative Matters
Acted for an Estate Trustee where the deceased was accused of corporate oppression, successfully defending an interim motion that sought to restrain the corporation from paying the defendants’ legal fees and awarding the plaintiffs interim legal fees, in Jonshal Enterprises Limited v. J.D.H. Holdings Limited et.al., 2025 ONSC 3216.
Acted for the court-appointed Litigation Guardian and Guardian of Property for an incapable person, and successfully responded to an appeal seeking to set aside the Guardian’s appointment, in Gefen v. Gefen, 2023 ONCA 406.
Acted for disinherited children in a will challenge involving a HNW estate, and successfully argued a critical interim motion for the appointment of an Estate Trustee During Litigation, in Cabrera v. Coughlan, 2022 ONSC 1087.
Acted for the estate trustee in seeking a declaration that a photocopy of a will was valid, and for directions regarding the validity of a pour-over clause to an inter vivos trust, in Vilenski v. Weinrib-Wolfman, 2022 ONSC 2116.
Successfully defended a motion seeking to tender a participant expert witness at trial, in Kuehl v. Ross, 2020 ONSC 838.
Acted for the Estate Trustee During Litigation during a contentious Application to remove estate trustees, in Mayer v. Rubin, 2017 CarswellOnt 21960.
Successfully defended a motion for security for costs, in Typhoon Offshore B.V. et al v. Jacob et al, 2017 ONSC 3715.
Successfully defended an application which sought to set aside an arbitration award on grounds of reasonable apprehension of bias, in Jacob Securities Inc. v. Typhoon Capital B.V., 2016 ONSC 604.
Successfully argued a motion for summary judgment to enforce a contract, in Bayer Inc. v. Belfield Investment Corp., 2015 ONSC 5029.
Selected Speaking Engagements
"Definition of a Dependant," Essential Skills for Estate Litigators: Litigating Threshold Issues, May 13, 2025.
"Recognising and Tackling Vulnerable Client Abuse," STEP Global Congress, Rome, Italy, February 25-26, 2025.
"Pitfalls in Capacity Litigation and Facilitating Solutions," OBA Elder Law Program, December 6, 2023.
"Orders For Directions” in Dependant Support Proceedings, Will Challenges, and Attorney/Guardianship Disputes, OBA Trust & Estate Law, May 16, 2023.
"Decision Making by the Declining Mind: How Friends and Family Can Help, and the Risk for Abuse," Aird & Berlis LLP Estates & Trusts Webinar, March 21, 2022.
"Overview of Common Will Challenges,” OBA's “Estate Litigation: A Primer” Webinar, February 22, 2022.
"Claims for Dependant Support," Junior Trust and Estate Practitioners (JTEP), July 19, 2021.
"Your First Estate Administration – Family Law Issues," OBA Trusts and Estates Law / Young Lawyers Division, June 17, 2021.
Selected Publications
Co-Author, "Estate Administration – Taxes, Clearance Certificates and Holdbacks," Tax Profile, July 2025.
Quoted in, "Red Alert" STEP Journal, May 23, 2025.
Co-Author, "Notable Trends and Challenges in Ontario’s Estates and Trusts Law," Lexpert, March 6, 2025.
Author, "When Money Claims Threaten an Estate, What Can a Trustee Do?" Aird & Berlis LLP, February 20, 2024.
Insights
Education
- TEP, Society of Trust and Estate Practitioners, 2021
- 39th Annual Osgoode Hall Intensive Trial Advocacy Workshop, 2018
- JD, University of Western Ontario, 2013
- BA, McGill University, 2007