Practice Areas
Estate Litigation
Trust Litigation
Capacity Litigation
Civil Litigation
Family Law Litigation
Child Protection Matters
Custody and Access Matters
Appeals
Bar Admissions
Ontario
Nova Scotia
Education
Bachelor of Management and Organizational Studies (Consumer Behaviour), Western University
Jessica is an associate lawyer at Tupman & Bloom LLP. Before joining T&B LLP, Jessica practiced at a boutique firm in Toronto where she focused exclusively on estates, trusts and capacity litigation. She articled at the Office of the Children’s Lawyer where she gained experience in the areas of estates, trusts, civil litigation, and family law. In that role, Jessica obtained valuable courtroom experience representing child clients in child protection and high conflict custody/access matters. Jessica then returned as counsel in the personal rights department where she assisted with appeals.
Jessica obtained her Juris Doctor from Osgoode Hall Law School. While at Osgoode, she was a caseworker at Parkdale Community Legal Services in the Social Assistance, Violence and Health Division where she represented clients before the Social Benefits Tribunal. She was a Dean’s Fellow for civil procedure and was elected as president of the Osgoode Women’s Network, the largest student group at Osgoode. Prior to attending Osgoode, she received her Bachelor of Management and Organizational Studies specializing in Consumer Behaviour from Western University.
Jessica also oversees the firm’s student program, supporting the development of the firm’s students through mentorship and training.
- Hurst v MacBeth Estate, 2026 ONSC 321
Successfully compelled production of estate administration records, including lawyers’ files for lawyers retained by the former estate trustees. - MacBeth Estate v Macbeth, 2025 ONCA 360
Successfully defended an appeal of a removal of estate trustee motion with an award of personal costs. - Bayliss v. Burnham, 2025 ONSC 5376
Successfully challenged the will on the basis of suspicious circumstances and insufficient evidence of knowledge and approval by the testator. - Bayliss v Burnham, 2024 ONCA 464
Successfully defended an appeal of a third-party production motion. - Reville v Weeks, 2024 ONSC 656
Successfully defended a will challenge on the basis that the will was not duly executed and the testator was unduly influenced. - Benjamin Cochrane Trust (Re), 2023 ONCA 546
Counsel on an appeal regarding a 14-day passing of accounts trial. - Bayliss v. Burnham, 2023 ONSC 7161
Successfully compelled third-party productions from a major tobacco company and obtained leave to examine two non-parties for discovery. - Trezzi v Trezzi, 2023 ONSC 4696
Successfully obtained an order for a holdback for legal fees for a professional estate trustee during litigation. - Mayer v Rubin et al, 2023 ONSC 4214
Successfully obtained one of the first known orders under s. 49(10) of the Estates Act for the appointment of an expert to assist the court on a passing of accounts. - Jonas v Jonas, 2022 ONCA 845
Successfully defended an appeal of an interpretation of a will. - Sasso v Sasso, 2022 ONCA 339
Successfully defended an appeal of a removal of estate trustee.
Publications
- A Matter of Discretion: Discretionary Trust and Trustee Decision Making, Estates Trusts & Pensions Journal, May 1, 2024
- Insolvent Estates: The Trustee Act and Debts Owing to the Crown, Ontario Bar Association Trusts and Estates Law Section, March 3, 2021
- Discouraging a “Kitchen Sink” Approach to Evidence Around Past Conduct in Child Protection Proceedings, Ontario Bar Association – Child and Youth Law Section, July 1, 2020
- COVID-19 Case Summaries, Ontario Family Law Reporter, May 1, 2020
Speaking Engagements & Panels
- Co-Chair & Speaker, “Essential Evidence Series for Estate Litigators”, Ontario Bar Association, July 15, 2025
- Speaker, “Your First Estate Litigation File”, Ontario Bar Association, May 13, 2025
- Speaker, Powers of Attorney and Guardianship Essentials, Ontario Bar Association, November 4, 2024
- Speaker, “Arguing a Motion in Estate Litigation”, Ontario Bar Association, July 26, 2023
- Co-Chair, “Your Guide to LSO Practice Reviews”, Ontario Bar Association, May 4, 2023
- Speaker, “How to Respond to a Notice of Objection”, Junior Trusts and Estates Practitioners, April 17, 2023
- Co-Chair, “Estate Litigation: A Primer”, Ontario Bar Association, February 22, 2022
Ontario Bar Association
The Advocates’ Society
Junior Trusts and Estates Practitioners Group (JTEP)
Women’s Legal Action & Education Fund (LEAF)