University of Calgary, Juris Doctor


Western University, BACS (Dean's Honour List)
Finance & Administration

Canadian Bar Association

Calgary Bar Association

Ontario Bar Association

Alberta Civil Trial Lawyers Association

Alberta Lawyers' Assistance Society


Pro Bono Alberta Law Review


Pro Bono Law Alberta

Advice Clinic

Pro Bono Ontario

Best Lawyers
Ones to Watch
Corporate & Commercial Litigation


Legal 500
Rising Star
Dispute Resolution: Ontario

Simon McCleary

Simon McCleary is an experienced litigation lawyer, with a focus in employment law and corporate & commercial disputes. He has demonstrated success across all levels of Court in Alberta and Ontario - as well as international arbitrations. Simon is known for his proactive approach to efficiently resolving complex matters and has a proven track record of delivering successful results for individuals and businesses alike.

He regularly acts for both employers and employees in cases involving wrongful dismissal, non-solicitation and non-competition disputes, employee fraud, human rights grievances, workplace investigations and benefits disputes.

Simon also represents businesses in commercial disputes across wide variety of sectors including manufacturing, telecom, retail, hospitality, commercial and residential real estate, insurance, oil & gas, and finance.

Experience as a Civil Litigation Lawyer

Simon has over a decade of civil litigation experience, including as an articling student and associate at JSS Barristers, as well as his work as a commercial litigation lawyer at an international law firm on Bay Street in Toronto.

Simon has been involved in a number of high-profile commercial matters, including:

  • Successfully defended an injunction application brought against an international hotel chain,
  • Co-counsel at a hearing before the Arbitration Institute of the Stockholm Chamber of Commerce for a Canadian auto-parts manufacturer,
  • Oversaw a significant portfolio of litigation for insurance company defending business interruption claims arising from COVID-19, and
  • Co-counsel in a lengthy and complex trial for client in the oil & gas services industry. The trial spanned three and a half months, where he was responsible for leading evidence of and cross-examining several key witnesses, including experts.

In employment matters, Simon has also been the lead trial lawyer in wrongful dismissal lawsuits, including as plaintiff’s counsel in two wrongful dismissal trials resulting in awards in excess of $200,000 and $500,000.


Simon was recently recognized by The Legal 500 Canada as a “Rising Star” in dispute resolution and “One to Watch” by Best Lawyers in Canada (corporate and commercial litigation).


Simon's legal acumen was recognized multiple times through awards and scholarships during his studies at the University of Calgary Faculty of Law, where he obtained a Juris Doctor. Such accolades included the LH Fenerty QC, Law Prize, Sean M. Smith Memorial Bursary in Criminal Law, Jason Lang Scholarship and Borden Ladner Gervais LLP Scholarship.

He also earned a bachelor’s degree from the University of Western Ontario - specializing in Finance & Administration as part of the Administrative & Commercial Studies program, where he was named to the Dean's Honour List.


"Am I Valid? Unpacking Termination Clauses in Employment Contracts"

JSS Barristers.ca, June 12, 2024 
Co-Author (with Filippo Titi)