Holly V.A. Cunliffe TEP


Admitted to the Ontario Bar: 2014

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  • Bio
  • Awards & Recognition
  • Professional Involvement
  • Representative Matters
  • Selected Speaking Engagements
  • Selected Publications
  • Insights
  • Education

Holly focuses on providing her clients with practical solutions to a wide range of estate, trust and capacity issues, helping her clients navigate through emotionally challenging litigation with compassion.

As a member of the firm’s Tax Group and Estates & Trusts Group, Holly represents individuals and trust companies with a range of court proceedings, such as will challenges, applications to pass attorney and trustee accounts, dependent support claims, rectification and interpretation of wills and trusts, variations of trust deeds, power of attorney and capacity disputes, estate and trust administration issues, trustee applications for advice and directions, appointment or removal of trustees/guardians, breaches of trust and guardianships. She is preferred counsel for LawPRO on matters of professional negligence with respect to estate and trust issues.

Holly is active in leadership positions: she has sat on the Executive Committee for the Ontario Bar Association’s Elder Law section since 2019, and has previously sat on the Executive Committee of the Trusts & Estates section. Holly is also an accredited Trust and Estate Practitioner (TEP) and is one of 12 global members of the Society of Trust and Estate Practitioners (STEP) elected to sit on the Mental Capacity Global SIG Steering Committee

Holly routinely appears before the Ontario Superior Court of Justice (including the Estates and Commercial Lists), and has also appeared before the Court of Appeal for Ontario.

Holly has additional experience in real estate disputes, contract disputes, oppression actions, civil fraud, asset and debt recovery, civil enforcement, employment disputes, product liability, judicial reviews and Indigenous law.

Holly is a long-standing volunteer with Pro Bono Ontario, providing free legal advice to low-income parties appearing in Small Claims Court, and taking calls on the Pro Bono Ontario Free Legal Advice Hotline providing advice on estates, powers of attorney, civil litigation and civil appeals.

Awards & Recognition

  • Recognized in The Best Lawyers in Canada in Trusts and Estates
  • Recognized as an Associate to Watch in Chambers HNW: The World's Leading High Net Worth Advisers for her expertise in Private Wealth Disputes (Canada)
  • Recognized in The Best Lawyers: Ones to Watch in Canada in Trusts and Estates

Professional Involvement


  • Mental Capacity Global SIG Steering Committee, The Society of Trust and Estate Practitioners
  • Canadian Bar Association
  • Ontario Bar Association
  • The Advocates' Society

Representative Matters

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

"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

Author, "When Money Claims Threaten an Estate, What Can a Trustee Do?" Aird & Berlis LLP, February 20, 2024.


  • 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