Gerald Chan

Practice Areas

Gerald practices criminal, administrative, and select civil litigation, with a special focus on white collar criminal and regulatory defence. He has been named one of the Top 25 Most Influential Lawyers in Canada (Canadian Lawyer, 2019), one of the Top 50 Trial Lawyers in Canada (Benchmark Litigation, 2023), White-Collar Crime/Enforcement Litigator of the Year (Benchmark Litigation, 2023), and Criminal Defence Lawyer of the Year (Best Lawyers, 2024).

Gerald has defended clients at trial and during investigations—including cases investigated by the OSC Joint Serious Offences Team, RCMP Integrated Market Enforcement Teams, OPP, Ministry of Labour, other government agencies, and special committees of boards of directors. Gerald also defends clients in a range of other matters, including sexual offences, cyber-crimes, and professional discipline.

In addition to his trial practice, Gerald often acts for clients on appeals and judicial reviews. He has been counsel in over 20 appeals in the Supreme Court of Canada (including cases on data privacy, foreign corruption, insider trading, and medical marihuana). He has been a longtime member of the Pro Bono Inmate Appeal Program, through which he argues appeals for marginalized inmates in the Court of Appeal for Ontario. He is also an advocacy advisor with the Supreme Court Advocacy Institute.

Gerald also acts for lawyers and law firms. He has defended lawyers in negligence claims, advised them on privacy breaches, represented their interests in ineffective assistance of counsel appeals, and defended them against conflict-of-interest allegations. He has also acted for lawyers facing subpoenas to testify in court.

Apart from his practice, Gerald is a prolific writer and teacher. He is co-author of the 8th and 9th editions of Sentencing (LexisNexis); co-author of the 1st and 2nd editions of Digital Evidence: A Practitioner’s Handbook (Emond Publishing); co-editor of Digital Privacy: Criminal, Civil and Regulatory Litigation (LexisNexis); and co-editor of Litigating Artificial Intelligence (Emond Publishing). He teaches on the faculty of the Federation of Law Societies of Canada’s National Criminal Law Program and the adjunct faculty of the University of Toronto, Faculty of Law (Criminal Procedure and the Criminal Appellate Externship).

Before joining Stockwoods, Gerald was a partner with Clayton Ruby at Ruby Shiller Chan Hasan, Barristers. Before that, Gerald practiced commercial litigation with a large firm and clerked for Justice Abella at the Supreme Court of Canada. He graduated as co-Gold Medallist from Osgoode Hall Law School.

In 2023, Gerald was elected Regional Bencher (for Toronto) of the Law Society of Ontario (LSO). He will serve as co-chair of the Equity and Indigenous Affairs Committee, and a member of the Professional Development and Competence Committee, Strategic Planning and Advisory Committee, and Treasurer’s Appointments Advisory Group. Gerald has also been appointed to the Hearing Division and Appeal Division of the Law Society Tribunal, and the Board of Trustees of the Law Foundation of Ontario.

Gerald previously served for six years as a member of the Judicial Appointments Advisory Committee, which is responsible for making recommendations to the Attorney General of Ontario for appointments to the Ontario Court of Justice.











Representative Work

White Collar | Quasi-Criminal

  • Successfully defended the former Chairman of CannTrust in an Ontario Securities Act prosecution in the Ontario Court of Justice, obtaining acquittals on all charges (including insider trading and securities fraud).
  • Defending a criminal fraud prosecution in relation to the syndicated mortgages offered by Fortress Real Developments Inc.
  • Representing individual tokenholders in a $16M crypto-fraud case regarding Indexed Finance (a decentralized finance platform)
  • Represented a former airline executive in a money laundering investigation by the Ontario Provincial Police, which was terminated without charges
  • Defended a large construction company in a workplace fatality prosecution by the Ministry of Labour and obtained a stay of all charges under s. 11(b) of the Charter
  • Regularly advising telecommunications companies and financial institutions on lawful access requests by law enforcement
  • Represented Uber partners in several jurisdictions (Toronto, Mississauga, etc.) and obtained withdrawals and stays of hundreds of charges of owning and operating a “taxicab” without a licence after lengthy motions on privilege and s. 11(b) of the Charter
  • Defended casino operators on charges under the Smoke-Free Ontario Act and obtained a withdrawal in one case and an acquittal in another
  • Defended a large food company facing mislabeling charges under the Food and Drugs Act and Criminal Code after an investigation by the Canadian Food Inspection Agency

Administrative and Public Law

  • Successfully defended the Toronto District School Board’s French Immersion program on judicial review
  • Represented Ryerson University in a labour grievance regarding the seizure of mail by police
  • Represented a large construction company in a coroner’s inquest related to a workplace fatality
  • Defended a lawyer in one of the first advertising-related prosecutions brought by the Law Society of Ontario
  • Represented a City Councillor and Vice-Chair of the Toronto Police Services Board on a judicial review application regarding the Board’s attempt to sanction him for speaking to the press

Supreme Court Advocacy

  • R v McGregor, 2023 SCC 4 (represented the David Asper Centre for Constitutional Rights in an appeal dealing with the extraterritorial application of the Charter)
  • R v Ramelson, 2022 SCC 44 (represented the B.C. Civil Liberties Association in an appeal dealing with the doctrine of entrapment in the context of cyber crime investigations)
  • R v JJ, 2022 SCC 28 (represented the Criminal Lawyers’ Association in two appeals dealing with the constitutionality of the Bill C-51 amendments to the sexual assault provisions in the Criminal Code)
  • R v Ghotra, 2021 SCC 12 (represented the B.C. Civil Liberties Association in an appeal dealing with entrapment in online police operations)
  • R v Le, 2019 SCC 34 (represented the Federation of Asian Canadian Lawyers and Chinese and Southeast Asian Legal Clinic on a joint intervention dealing with racial profiling and police detentions in racialized communities)
  • R v Mills, 2019 SCC 22 (represented the Criminal Lawyers’ Association in an appeal involving the right to privacy in text messages with an undercover officer)
  • vMarakah, 2017 SCC 59R v Jones, 2017 SCC 60 (represented the B.C. Civil Liberties Association in two companion appeals on text message privacy)
  • R v Peers, 2017 SCC 13 (represented the B.C. Civil Liberties Association in an appeal dealing with the right to a jury trial in Securities Act prosecutions)
  • World Bank Group v. Wallace, 2016 SCC 15 (represented the B.C. Civil Liberties Association in an appeal dealing with a Corruption of Foreign Public Officials Act prosecution)
  • R v Smith, 2015 SCC 34 (represented the Criminal Lawyers’ Association in an appeal dealing with the constitutionality of medical marihuana regulations)

Criminal Defence

  • R v XC, 2020 ONSC 410 (argued one of the first motions to interpret the new sexual assault provisions brought about by Bill C-51, and obtained an acquittal on all charges at trial)
  • R v Adler, 2020 ONCA 246 (obtained substituted acquittals in a sexual offences case after the ONCA concluded that all of the evidence should have been excluded)
  • R v John, 2018 ONCA 702 (conviction and sentence appeal in the ONCA in which the court struck down the mandatory minimum sentence for possession of child pornography)
  • R v Levin, 2015 ONCJ 290 (defended a former Deputy Minister in a prosecution for computer crimes and sexual offences)
  • R v Yowfoo, 2013 ONCA 751 (obtained a substituted acquittal in a case involving serious drug trafficking and firearms charges)
  • United States of America v Chu, [2009] OJ No 3091 (SCJ) (represented the person sought in an extradition case involving Canadian gathered wiretap evidence)




Additional Info

Awards and Recognition

  • Canadian Lawyer, Top 25 Most Influential (2019)
  • Thomson Reuters Stand-out Lawyer (formerly known as Acritas Star) – nominated as stand-out lawyer by senior in-house counsel (2021-2022)
  • Benchmark Litigation, White-Collar Crime/Enforcement Litigator of the Year (2023)
  • Benchmark Litigation, Top 50 Trial Lawyers (2023)
  • Benchmark Litigation, “Litigation Star”, Criminal and White Collar Crime (2019-2023)
  • Benchmark Litigation, “Future Star”, Criminal and White Collar Crime (2017-2018)
  • Benchmark Litigation, “40 & Under Hotlist” (2017-2021)
  • Benchmark Litigation, “Emerging Talent of the Year” (2018)
  • Chambers Canada, White-Collar Crime and Government Investigations, Band 3 (2024); Band 4 (2023); Up and Coming (2021-2022)
  • Chambers Canada, Crime, Band 2 (2024)
  • Lexpert Legal Dictionary, Litigation – Public Law, “Most Frequently Recommended” (2022-2023)
  • Lexpert Legal Dictionary, Litigation – Public Law, “Repeatedly Recommended” (2019-2021)
  • Lexpert Legal Dictionary, Litigation – Public Law, “Leading Lawyers to Watch” (2017-2018)
  • Lexpert, “Rising Star” (2017)
  • Lexpert Guide to the Leading US/Canada Cross-Border Litigators (2014, 2017-2018)
  • Best Lawyers in Canada, Criminal Defence; Appellate Litigation (2019-2024)
  • Best Lawyers in Canada, Administrative & Public Law (2017-2024)
  • Best Lawyers in Canada, Privacy & Data Security (2020-2024)
  • Crescent School Alumni Excellence Award (2020)
  • Precedent Setter Award, Precedent Magazine (2012)
  • Osgoode Alumni Gold Key, One-to-Watch, Osgoode Hall Law School (2012)
  • Gold Medal, Osgoode Hall Law School (2006)


Associate editor, Canadian Rights Reporter (2009-present)

Co-editor, For the Defence (2015-2019)

Co-editor, Litigating Artificial Intelligence (Emond Publishing, 2021)

Co-Author, Digital Evidence: A Practitioner’s Handbook, 2nd ed. (Emond Publishing, 2021)

Co-Editor, Digital Privacy: Criminal, Civil and Regulatory Litigation (LexisNexis, 2018)

Co-Author, Digital Evidence: A Practitioner’s Handbook (Emond Publishing, 2017)

Co-Author, Sentencing, 9th ed. (LexisNexis, 2017)

Co-Author, “Clay Ruby: Activist, Mentor and Friend”, The Advocates’ Journal (December 2022)

Author, “The virus of anti-Asian prejudice”, Toronto Star (April 14, 2020)

Author, “R v Le: Race, Reality and the Rule of Law”, LSO Six-Minute Criminal Lawyer 2020

Author, “Litigating Algorithms: A Defence Perspective”, LSO Special Lectures 2019: Innovation, Technology, and the Practice of Law (November 21, 2019)

Co-Author, “Challenges to Privilege in the Internal Investigation Context”, CCCA Magazine (Spring 2019)

Co-Author, “A Purposive Approach to Privilege in the Context of Internal Investigations”, The Advocates’ Quarterly (February 2019)

Author, “Text Message Privacy: Who Else Is Reading This?”, Supreme Court Law Review (2018)

Co-Author, “Privilege and Corporate Responsibility: Are courts impeding public policy?”, Global Investigations Review (10 May 2018)

Author, “Text messaging: The most private (and recorded) form of communication”, The Advocates’ Journal (March 2018)

Teaching & Speaking Engagements

Panelist, “Strategies for Success from the Bar”, The Advocates Society: Joining the Party: The Ins and Outs of Interventions (February 8, 2024)

Panelist, “Defending White Collar Crime and Regulatory Cases”, Criminal Lawyers’ Association in Cancun (January 21, 2024)

Panelist, “Concurrent Prosecutions”, Osgoode PD: Sexual Assault Cases in the Criminal Court (November 24, 2023)

Panelist, “Technology and Its Use in International Law”, Canadian Institute for the Administration of Justice: The Law of Borders (October 26, 2023)

Co-Chair, “Anti-Money Laundering: Protecting Your Litigation Practice”, Law Society of Ontario (October 17, 2023)

Panelist, “AI: Promises and Pitfalls”, National Judicial Institute & Canadian Superior Court Judges Association: Judging Better, Judging Smarter (July 6, 2023)

Panelist, “OHSA Prosecutions and the Charter”, OBA: Litigating Compliance Issues Under Ontario’s Occupational Health and Safety Act (May 29, 2023)

Panelist, Financial Services Regulatory Authority: Asian Heritage Month Event (May 29, 2023)

Panelist, “New Client Law Society Rules and Ethical Challenges for Lawyers”, Osgoode PD: 14th National Symposium on Money Laundering and Financial Crimes (May 26, 2023)

Panelist, “Search Warrant Execution: Are You and Your Clients Ready?”, LSO: White Collar Crime Update for Litigators (May 9, 2023)

Panelist, “Law and Artificial Intelligence”, Federal Court Retreat (May 4, 2023)

Co-Chair, “Digital Evidence for Litigators”, The Advocates’ Society (March 28, 2023)

Speaker, “Digital Privacy and Criminal Law”, Manitoba Bar Association (February 23, 2023)

Panelist, “Practical Insights for Young Litigators: Forging a Path in Appellate Advocacy”, Ontario Bar Association (February 23, 2023)

Panelist, “Reconsidering the Extra-Territorial Application of the Charter”, Osgoode PD: 20th National Symposium on Search and Seizure Law in Canada (February 3, 2023)

Co-Chair, “Conference to Celebrate the Retirement of the Honourable Justice Rosalie Silberman Abella from the Supreme Court of Canada”, uOttawa Public Law Centre / CIAJ (May 12-13, 2022)

Presenter, “Charter Issues: s. 11(b) Update”, Law Society of Ontario Six Minute Criminal Lawyer (April 30, 2022)

Co-Chair, “Digital Evidence for Litigators”, The Advocates’ Society (March 30, 2022)

Panelist, “Key Principles for Drafting Proper Affidavits”, The Advocates’ Society: Legal Drafting for Litigators (February 14, 2022)

Panelist, “Text Messages Here, There and Everywhere; Marakah five years on”, Osgoode PD 19th National Symposium on Search and Seizure Law in Canada (February 4, 2022)

Panelist, “Advocacy Primer: Drafting Persuasive Facta”, Ontario Bar Association (January 18, 2022)

Panelist, “AI Decision-Making: Protecting Rights Through Litigation and Regulation in Canada and the United States”, Law Commission of Ontario (December 9, 2021)

Panelist, “Cybersecurity: Assessing Liability arising from Information Security Breaches in Data Privacy”, CAN-TECH Law Annual Conference (October 21, 2021)

Panelist, “Sexual Assault Lawyer’s Toolkit”, DCAO/CCLA Criminal Law Conference (October 16, 2021)

Co-Chair, “Digital Evidence Workshop”, The Advocates’ Society (August 10, 2021)

Panelist, “Client Management Mistakes”, The Advocates’ Society, Trial and Error: Lessons Learned From Career Mistakes (July 6, 2021)

Panelist, “Your First Time at the Supreme Court of Canada? It’s Not So Scary”, The Advocates’ Society: Supreme Court of Canada Advocacy (May 27, 2021)

Panelist, “Machine Learning, Automated Decision and Facial Recognition”, OBA Privacy Law Summit (May 4, 2021)

Panelist, “Dealing with Concurrent Proceedings Affecting the Corporation”, Law Society of Ontario: Emerging Issues in Directors and Officers Liability (April 26, 2021)

Panelist, “The Impact of AI on Issues of Access to Justice, Equity, Diversity & Inclusion”, Law Society of Ontario: AI for Litigators (April 16, 2021)

Panelist, “Adapting Your Oral Advocacy Skills to Succeed in this New Era of Remote Proceedings”, CBA Webinar (April 6, 2021)

Co-Chair, “Digital Evidence for Litigators”, The Advocates’ Society (March 10, 2021)

Panelist, “Demonstration and Discussion: Effective Advocacy in the (Virtual?) Courtroom”, The Advocates’ Society: Motions Advocacy (March 4, 2021)

Panelist, “Sealing Orders”, Osgoode PD: 14th Annual Intensive Course on Drafting and Reviewing Search Warrants (March 1, 2021)

Panelist, “OMG: Tech Horror Stories and the Lessons Learned”, The Advocates’ Society: Technology Gone Wrong: Cautionary Tales From the Remote Courtroom (February 26, 2021)

Co-Chair, 14th Annual FACL Ontario Conference & Mixer, Federation of Asian Canadian Lawyers, Ontario (February 18-20, 2021)

Panelist, “Disruption Triggering Setbacks: Privilege Fights Back”, RODA’s 6th Annual Diversity Conference (December 7, 2020)

Instructor, “24th Annual Course on Written Advocacy”, Osgoode PD / The Advocates’ Society (November 9, 11, 17, 19, 2020)

Panelist, “Difficult Conversations: How to Build Cultural Inclusion”, The Advocates’ Society: Equality, Diversity and Inclusion for Litigators (October 8, 2020)

Panelist, “Issues in criminal, civil, and regulatory litigation – when can you access evidence from one proceeding and use it in another?”, Criminal Lawyers’ Association (July 22, 2020)

Speaker, “R v Le: A Defence Perspective”, Law Society of Ontario: Six Minute Criminal Lawyer 2020 (April 2020)

Co-Chair, “Digital Evidence for Litigators”, The Advocates’ Society (February 26, 2020)

Conference Co-Chair, 13th Annual FACL Conference (February 8, 2020)

Panelist, “Finding Your Voice: How to Know what Business Development Strategy to Implement”, The Advocates’ Society (January 24, 2020)


  • Law Society of Ontario, Regional Bencher (Toronto)
  • Law Foundation of Ontario, Board of Trustees
  • Member, Criminal Lawyers’ Association (Ontario)
  • Member, The Advocates’ Society
  • Member, Federation of Asian Canadian Lawyers (Ontario)
- Find a Lawyer -