Douglas Montgomery

Douglas Montgomery is a top lawyer recognized by Best Lawyers in the practice area(s) of Administrative and Public Law.

Douglas 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. Douglas, who practices law in Toronto, Ontario, has been recognized since 2026. This recognition is based on an exhaustive peer-review survey, reflecting the high esteem in which Douglas is held by other top lawyers in the same geographic and legal practice area.