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Douglas Montgomery

B.A. (Hons.), M. Phil., J.D.

Douglas Montgomery

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Douglas Montgomery is a thoughtful and strategic litigator at Paliare Roland Rosenberg Rothstein LLP, where his practice encompasses complex contractual and commercial disputes, public and administrative law, and professional discipline and regulation. He has represented individuals, corporations, community organizations and regulators at every level of court in Ontario, as well as the Federal Court, the Federal Court of Appeal, and the Supreme Court of Canada. 

Before joining the firm as an associate, Douglas clerked for the Honourable Michael J. Moldaver at the Supreme Court of Canada. Prior to his legal career, he worked in the public sector on regulatory modernization initiatives at a federal Crown Corporation. As a law student, Douglas received several awards for outstanding academic and moot court performance, including the Canadian Bar Association’s Paul Smith Memorial Essay Award.
 
In addition to his practice, Douglas contributes to legal education as an adjunct professor at Osgoode Hall Law School, where he teaches statutory interpretation. He has also been recognized as a Best Lawyer: “Ones to Watch” in Administrative and Public Law.

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Education

  • Osgoode Hall Law School, J.D., 2018
  • University of Bergen (Norway), M.Phil, 2009
  • University of Alberta, B.A. (Hon.), 2007

Bar Admissions

  • Ontario, 2019

Professional Affiliations

  • The Advocates’ Society
  • The Ontario Bar Association
  • The Osgoode Society for Legal History

Practice Areas

Awards and Honours

  • Best Lawyers: Ones to Watch in Canada 2026 - Administrative and Public Law

Representative Work

Quadrangle v. Attorney General of Canada: represented a major telecommunications investor in a complex trial against the Government of Canada alleging negligence and negligent misrepresentation, ultimately securing a judgment worth approximately $555 million (excluding costs and interest): 2025 ONSC 4526

Power Workers Union v. Canada (Attorney General): represented a trade union in a complex arbitration involving drug and alcohol testing in nuclear facilities, and in a related constitutional challenge in Federal Court to a regulatory instrument imposing drug and alcohol testing in nuclear facilities. Obtained successive interim stays from the arbitrator and the Federal Court of the implementation of drug and alcohol testing in nuclear facilities, pending final disposition: 2022 FC 73, 2023 FCA 215.

Warren v. Canaccord Genuity Corp: brought successful action for wrongful dismissal and breach of contract on behalf of an investment banker. Obtained over $2.5 million in damages following successful trial: 2026 ONSC 547

Re Eastern Meat Solutions Inc. et. al.: represented a commercial real estate developer in successfully resisting an injunction to prevent the developer from drawing on a letter of credit in the context of a CCAA proceeding.

Royal College of Dental Surgeons of Ontario v. Alsoma: brought contempt proceedings on behalf of a regulator against an unlicensed practitioner, ultimately securing a significant penalty: 2024 ONSC 1924. 

College of Nurses of Ontario v. Brodsky: acted on behalf of a professional regulator in obtaining findings of fraud against a member in a contested hearing based on circumstantial evidence. These findings were upheld on appeal: 2025 ONSC 3422 (Div. Ct.).

Acted on behalf of the College of Nurses of Ontario in defending applications for judicial review and statutory appeals: 2023 ONSC 3735, 2024 ONSC 1497, 2025 ONSC 6295.

Acted in receiverships on behalf of receivers, purchasers, creditors and debtors in a large array of matters, including applications for receiverships and motions for approval and vesting orders.

Spina v. Shoppers Drug Mart: represented a class of pharmacist franchisees against their franchisor alleging breach of contract, breach of duties of good faith, and unjust enrichment in connection with payments from pharmaceutical companies and franchisor fees and practices: 2023 ONSC 1086, 2024 ONCA 642.

MacDonald et. al. v. BMO Trust Company et. al.: represented a class of registered accountholders against investment brokerages and a trust company alleging breach of trust and breach of fiduciary duty in connection with foreign exchange fees: 2021 ONSC 3726.

Varley v. Canada (Attorney General): representing a class of Indigenous persons who were apprehended and placed in the care of non-Indigenous foster or adoptive parents alleging the federal government had (and breached) a fiduciary duty and a common law duty of care towards class members.

Saskatchewan (Environment) v. Métis Nation – Saskatchewan: intervened on behalf of a community organization at the Supreme Court in a case about the application of the abuse of process doctrine in the context of ongoing proceedings where Indigenous rights are asserted: 2025 SCC 4.

York Region District School Board v. Elementary Teachers’ Federation of Ontario: intervened on behalf of a union at the Supreme Court in a case involving the search and seizure of employee files in a unionized workplace: 2024 SCC 22.

Burjoski v. Waterloo Region District School Board: intervened on behalf of a leading community organization, EGALE, in an appeal of an anti-SLAPP motion: 2024 ONCA 811.