Simon Chester Counsel Head – Client and Matter Acceptance Team

Speaks:  English

Year of Call: 1988 - England & Wales

Year of Call: 1982 - Ontario

Primary phone: +1 416-369-7263

Fax: +1 416-862-7661


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Primary office:  Toronto

Practice areas:

Simon Chester

Simon Chester is counsel for conflicts and regulatory matters in Gowling WLG's Toronto office, and the leader of the firm's Client and Matter Acceptance Team.

For 30 years, he has helped law firms navigate the complex and shifting landscape of professional regulation and solve an array of professional crises that threaten regulatory compliance, liability risk and reputational harm. With roots in three continents, Simon is a global lawyer and is qualified in both Europe and North America.

Simon is one of Canada's leading experts on conflicts of interest, and was instrumental in preparing the 2008 Report of the CBA Task Force on Conflicts of Interest. Before joining Gowling WLG, he was general counsel to a major Canadian law firm, including handling the regulatory aspects of its dissolution. His legal career includes a decade of public service, 30 years of experience as a Bay Street partner with large national firms and teaching at Osgoode Hall Law School. He is also the co-founder of, one of the most widely read legal blogs in Canada.

Within large law firms, he has acted as the firm's lawyer, handling conflicts of interest, risk management, regulatory compliance and professional crises. He has also been a pioneer in applying advanced technologies to the practice of law, and in adapting global law firms to emerging conflicts, multiple regulators, security issues and systems aspects of data protection.

Practice areas

Career & Recognition

Filter timeline:
  • 2003

    • Education
      Osgoode Hall Law School, LLM
  • 1988

    • Qualifications (Year of Call/Admission, etc.)
      Year of Call, England & Wales
  • 1982

    • Qualifications (Year of Call/Admission, etc.)
      Year of Call, Ontario
  • 1979

    • Education
      University of Oxford, BA, MA


  • American Bar Association: Former chair - American Bar Association TechShow, Law Practice Magazine Editorial Board, Education Board, New Media and Internet Board
  • Canadian Bar Association: Consultant on conflicts of interest; member task force on conflicts of interest
  • College of Law Practice Management: Former president