About James H. Bennett

James H. Bennett, who goes by Jamie, is senior counsel at Bennett Grant LLP in Kitchener and has been settling claims and disputes for more than 40 years. Jamie's civil litigation practice is wide ranging, but its core is defending liability insurers, who bring Jamie in as preferred counsel when professionals, municipalities or police officers are sued. Peers took note in 2018, when the Waterloo Region Law Association presented Jamie with its Coulter A. Osborne Award, which honours a member's integrity, comity and beneficence in practice and in public life.

Cambridge is home turf: Jamie was born and grew up there, and while Jamie now lives as well as works in Kitchener, family life stayed tied to Cambridge, where the children went to school. Jamie articled at the firm in 1979 and became a partner in 1984. Alongside private practice, Jamie serves as a Deputy Judge of the Small Claims Court, part of the Ontario Superior Court.

Cases have gone as far as the Supreme Court of Canada, with stops at the Superior Court of Justice, the Divisional Court and the Court of Appeal for Ontario along the way. In 2022 Jamie appeared for the Region of Waterloo at the hearing of its Superior Court application to evict residents of an encampment on regionally owned land in downtown Kitchener.

Jamie is a certified mediator and an arbitrator with a long record in family, estate, commercial and insurance matters, and has lectured for audiences as varied as the Waterloo District School Board, Conestoga College, Wilfrid Laurier University and the Advocates' Society.

Practice areas

Insurance defence for professionals, municipalities and police

Liability insurers retain Jamie as preferred counsel to defend claims made against professionals, municipalities and police officers.

Civil litigation

Jamie's litigation is limited to civil matters, mainly personal injury, estate matters, shareholder disputes, and insurance claims and coverage. Jamie has had cases before the Superior Court of Justice, the Divisional Court, the Court of Appeal for Ontario and the Supreme Court of Canada.

Estate litigation

Jamie is one of the contacts for the firm's estate litigation group, and estate matters are a regular part of Jamie's civil caseload.

Mediation and arbitration

As a certified mediator and an experienced arbitrator, Jamie helps parties resolve family, estate, commercial and insurance disputes outside of court.

Debt recovery

Jamie is one of the lawyers in the firm's debt collection and recovery group.

Education & credentials

  • Undergraduate studies, University of Western Ontario
  • Law school, University of Windsor
  • Certified Mediator

Notable cases

  • Rivers v. Waterloo Regional Police Services Board, 2019 ONCA 267

    Jamie acted for the respondent Waterloo Regional Police Services Board. The court dismissed the appeal from an order that had dismissed the proposed class action for want of jurisdiction, and the Supreme Court of Canada later dismissed an application for leave to appeal with costs.

Decisions where James H. Bennett appeared as counsel, from public court records. Past cases don't predict future results.

Awards & recognition

Memberships & affiliations

In the community

  • Jamie spent many years on the board of the local Family and Children's Services and also served on the Board of the Grand River Hospital.
  • Earlier volunteer work included time as a Big Brother and as a Cancer Society volunteer.

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This listing was generated by AI from public sources in October 2026. It may contain errors, and we can’t guarantee it’s accurate or complete. Before you rely on anything here, verify it on their firm’s website. Confirm James H. Bennett’s licence and standing in the Law Society of Ontario directory ↗

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