Stephen Aylward

Practice Areas

Stephen practices white collar defence and fraud recovery, commercial litigation, and administrative/regulatory law. He specializes in complex litigation, investigations, and appeals. He combines insights from administrative, criminal, and civil practice to bring a fresh perspective to legal problems.

Stephen has appeared before all levels of court, including the Ontario Court of Appeal and the Supreme Court of Canada. He regularly publishes and speaks on legal topics and his writing has been cited by the Supreme Court. Stephen has taught as an adjunct professor of contract law at the University of Toronto’s Global Professional LLM program.

Prior to joining Stockwoods in 2014, Stephen served as a law clerk to the Hon. Justice Thomas Cromwell at the Supreme Court of Canada. He holds a J.D. from the University of Toronto Faculty of Law and a law degree from the University of Oxford, where he studied as a Rhodes Scholar. He also holds a B.A. (Hons.) from McGill University. He has completed the Level I examinations of the Chartered Financial Analyst (CFA) Program.

Stephen is a director of Fighting Blindness Canada, Canada’s leading vision research charity. He is a director and past president (2017-2019) of the Canadian Association of Rhodes Scholars. He is a director and past president (2016-2019) of a federal riding association.


Representative Work

Continental Currency Exchange Canada Inc. v. Sprott, 2023 ONCA 61. Successfully acted for the respondents in a major commercial dispute regarding an aborted transaction to form a new bank.

Public Order Emergency Commission. Acted as counsel for the Government of Canada in the public inquiry into the Government’s decision to invoke the Emergencies Act in February, 2022 in response to the “Freedom Convoy” occupation of Ottawa and border blockades.

Re Indexed Finance. Representing individual tokenholders in a $16M crypto-fraud case regarding Indexed Finance (a decentralized finance platform)

Crestwood Preparatory College Inc. v. Smith, 2022 ONCA 743. Acted for the moving party in obtaining a stay of proceedings for abuse of process by non-disclosure of partial settlement agreements.

Karygiannis v. Toronto (City), 2020 ONCA 411

Acted for a fair elections advocate in legal proceedings to remove a Toronto City Councillor from office for campaign finance violations.

Bowman v. Martineau, 2020 ONCA 330

Successfully acted for a real estate agent in the leading case on the measure of damages in cases of professional negligence.


Additional Info

Awards and Recognition

Benchmark Litigation: Emerging Talent Litigator of the Year (2024)

Thomson Reuters: Client-Nominated Stand-Out Lawyer (2024, 2023)

Best Lawyers: Ones to Watch in Canada (Appellate Practice, Corporate and Commercial Litigation, Administrative and Public Law) (2024)

Benchmark Litigation: Future Star (2023)

Toronto Lawyers Association: Emerging Excellence Award (2022)

Precedent Magazine: Precedent Setter (2021)


  • Author, “A Shifting Landscape: Non-Disclosure of Partial Settlements in Multi-Party Litigation” in The Annual Review of Civil Litigation (2023) (Thomson  Reuters, forthcoming)
  • Author, The Law of Unincorporated Associations in Canada (LexisNexis, 2020)
  • Author, “Cross-Border Double Jeopardy in Canada”, For The Defence, May 2019.
  • Author, “Search and Seizure of Third Party Information”, in Nader Hasan & Gerald Chan, eds., Digital Privacy: Criminal, Civil, and Regulatory Litigation (LexisNexis, 2018).
  • Author, “Why Canada Needs Deferred Prosecution Agreements”, The Globe and Mail, 7 June 2018.
  • Author,  “Technological Neutrality or Novelty? Two Models of Privacy in the Digital Era” Supreme Court Law Review (2017).
  • Author, “Does Chief Justice McLachlin’s successor have to be from Quebec?”, The Toronto Star, 18 July 2017.
  • Co-Editor, with Pam Hrick, The Supreme Court Law Review, Vol. 80 (2017), “Essays in Celebration of the Hon. Thomas A. Cromwell” (LexisNexis).
  • Co-Author with Nader Hasan, “Password protection a crucial Charter right,” The Toronto Star, 23 August 2016.
  • Co-Author with Gerald Chan, “FBI v. Apple and Beyond: Encryption in the Canadian Law of Digital Search and Seizure,” Journal of Data Protection & Privacy(London: Henry Stewart Publications, forthcoming).
  • Co-Author with Gerald Chan, “We need stronger limits on Apple-style court orders”, The Globe and Mail, 19 March 2016.
  • Co-Author with Brian Gover, “Informed Consent: From Material Risks to Material Information”, Dispatch Magazine, February/March 2016
  • Co-Author with Luisa Ritacca, “The Public Policy of Insurance against Administrative Monetary Penalties” (2015) 12 Regulatory Boards and Administrative Litigation 734.
  • Co-Author with Samuel Robinson, “Requisitioned Meetings of Shareholders: An Uneasy Balance of Powers”, (2015) 44 The Advocates Quarterly 509.
  • Co-Author with Luisa Ritacca, “In Defence of Administrative Law: Procedural Fairness for Administrative Monetary Penalties,” (2015) 28 Can J Admin Law & Practice 35.
  • Author, “The Idea of Privacy Law: Jones v Tsige and the Limits of the Common Law” (2013) 71 University of Toronto Faculty of Law Review 61.

Teaching & Speaking Engagements

  • “Corruption Without Borders: Information Sharing in International White Collar Investigations” presented to the International Society for the Reform of Criminal Law, July 10, 2017, San Francisco.
  • “Administrative Law: Year in Review”, 16th Annual Advanced Administrative Law & Practice Conference, Ottawa, ON, October 25, 2016.
  • “D&O Liability Insurance Coverage for Administrative Monetary Penalties”, Advocates Society Sixth Annual Securities Symposium, Toronto, ON, September 12, 2016.
  • “Data Encryption and Digital Privacy in Canada, the United States, and the United Kingdom”, the International Society for the Reform of Criminal Law 29thInternational Conference, Halifax, Nova Scotia, July 27, 2016.


  • Member of the Board of Directors of Fighting Blindness Canada, Canada’s largest vision research charity.
  • While at Oxford, Stephen won the Gibbs Prize for the highest average mark in tort, contract, trusts, and land, as well as the Field Fisher Waterhouse Prize for the highest mark in EU law.
  • Stephen’s writing on administrative monetary penalties has been cited by the Supreme Court of Canada (Guindon v. Canada, 2015 SCC 41).
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