Derek M. Olson
Derek M. Olson is a senior civil litigator recognized for his leadership in complex, high-stakes disputes. He joined Olschewski Davie LLP to lead the firm’s advocacy in matters requiring sophisticated procedural strategy and appellate expertise.
Derek’s reputation as a "heavy hitter" in civil litigation is built on a foundation of excellence. After graduating third in his class from Law School—achieved while working full-time as a Teaching Assistant and special researcher—he honed his craft at the city's top firms. He later became a named partner at a firm widely recognized at the time as Western Canada's premier litigation boutique.
His practice is defined by "hard litigation"—matters turning on intricate questions of law and complex evidentiary records. This expertise has taken him beyond Manitoba; he has collaborated with counsel across Canada and litigated matters in Toronto and Ottawa. He has acted for a diverse range of clients, including major Insurers, Land Developers, Banks, Manufacturers, Farm Implement Companies, Family Farms, Livestock Producers, Injured Individuals, Professionals, etc. Despite this high-level focus, Derek remains committed to serving clients from all walks of life, with a dedicated interest in representing marginalized groups and individuals.
The Phoenix Sinclair Inquiry
A defining moment in Derek’s public law career was his invitation to serve as Associate Commission Counsel to the late Honourable Ted Hughes, Q.C., on the Phoenix Sinclair Inquiry. Working alongside Sherri Walsh, Q.C., Derek helped lead the Commission through one of the most significant public inquiries in the province's history, resulting in transformative changes to the Child Welfare System.
Professional Leadership & Education
Derek is a pillar of the legal education community. He served as an Instructor at Robson Hall, teaching Civil Procedure to the next generation of litigators. He has also served as an expert panelist for the Law Society of Manitoba (LSM) and edited materials for the Bar Admission Course (now PREP). His adjudicative experience includes sitting on the Insurance Adjusters Appeal and Review Board and serving on professional regulatory panels.
Appellate & Complex Litigation
Derek has extensive trial and appellate experience, having appeared as counsel in significant trials at all levels of the Manitoba courts, as well as the Federal Court of Appeal and the Supreme Court of Canada.
Primary Areas of Focus:
Public Law & Inquiries: Acting as Commission Counsel in major public inquiries (Phoenix Sinclair) and advising on government liability.
Medical Malpractice & Personal Injury: Representing patients and families in cases of catastrophic injury, surgical negligence, and wrongful death.
Commercial & Shareholder Disputes: Handling oppression remedies, corporate governance disputes, and construction litigation.
Indigenous Law: Advising First Nations on sovereignty, governance, and Treaty rights.
Estate Litigation: Resolving contentious estate matters and fiduciary disputes.
Arbitration & Mediation: Acting as counsel in alternative dispute resolution to achieve efficient settlements.
Public Interest Law: Advocacy in landmark cases, including successfully seeking Intervenor status for a major advocacy organization at the Manitoba Court of Appeal in R. v. Mabior.
