Jason Reynar

Practice highlights

Biography

With a career spanning nearly two decades, Jason has held pivotal public sector roles including Chief Administrative Officer, Municipal Solicitor, Municipal Clerk, Utilities Board Chair, and Vice President (Strategy) of a regional health centre. His leadership in advising and managing complex municipal teams, projects and substantial budgets ($1B+) has driven significant advancements in infrastructure, sustainability, and quality of life improvements for communities across Ontario.

Jason’s direct experience with intricate legal and governance issues, including successful advocacy, negotiation, and unique public sector (re)structuring, makes him an invaluable trusted advisor for municipalities and other public entities looking to navigate legal complexities, changing legislative and regulatory environments, and unprecedented growth and development. His visionary approach and proven track record in providing well-researched advice, fostering innovation and supporting fiscal sustainability have earned him recognition and respect across the sector.

Jason has been privileged throughout his career to lead teams that have helped reshape services, programs and/or infrastructure; for example:

• Oversight of the largest in-land marina resort development in North America;
• Establishing the first municipal services corporation in Ontario to own water and wastewater assets;
• Creating the global-first public transit system powered by ride-sharing;
• Collaborating to create unique partnerships, corporate structures, or special purposes entities (e.g., health and wellness partnership);
• Activating public land to create affordable housing initiatives that ensure long-term, below-market ownership costs; and,
• Establishing the first acceptance of cryptocurrency for the payment of real property taxes, as well as knowledge of digital municipal bond offerings.

Jason has appeared before the Ontario Superior Court of Justice (including Divisional Court, Family Court, and Small Claims Court), the Ontario Land Tribunal, and the Ontario Human Rights Tribunal. As a litigator, Jason has represented clients in a diverse range of matters including complex commercial disputes, defamation, medical malpractice, and class action municipal defence. Jason adeptly drafts memoranda, pleadings, facta, and affidavits that support his successful client advocacy in mediations, negotiations, and settlements.

Jason is an Adjunct Professor in the School of Public Policy & Administration at York University, teaching in both the master and undergraduate programs; Co-Director of Osgoode Hall Law School’s Certificate in Municipal Law; Executive Member of the Ontario Bar Association Municipal Law Section. He also volunteers his expertise as a Board Member for Habitat for Humanity Huronia and the Lambton Centre for Kids.

Jason has provided advice on the following municipal and public law matters, including the practices, procedures, methods and mandates pertaining thereto:

• Annexation and boundary issues
• Closed meeting investigations
• Conflict of interest advice, training, and integrity commissioner advice and complaint investigations
• Contract drafting and review (e.g., municipal capital facility agreements)
• Data governance and management
• Deal structuring and advice
• Enabling economic development (e.g., scope of authority, partnership agreements)
• Good governance training and advice
• Incentive structures (e.g., advancing affordable housing)
• Information privacy and appeals to the Information and Privacy Commissioner
• Land use planning & development
• Licensing and approval authority reviews
• Negotiating agreements with agencies, boards and commissions (e.g. conservation authorities and libraries)
• Policy and by-law review
• Public-private partnerships
• Structuring municipal services corporations and other utility matters
• Ward boundary reviews

Jason’s experience also includes being a former member of the following:

• Board of Directors for the Ontario Association of Municipal Administrators (“OMAA”);
• Municipal Law Departments of Ontario Association (“MLDAO”);
• Association of Municipal Clerks & Treasurers (“AMCTO”); and,
• COVID-19 Technical Working Group of the City of Toronto, Association of Municipalities of Ontario (“AMO”), and the Ministry of Municipal Affairs and Housing (“MMAH”).

Selected Publications/Presentations

• Co-Author, “A Sign of the Times: Balancing Freedom of Expression and Community Standards”. Lerners Insights, December 12, 2025.
• Co-Chair, “Professionalism for Municipal and Planning Lawyers”, Ontario Bar Association. Toronto, December 4, 2025.
• Co-Presenter, “The Changing Role of Municipalities in Development – From Regulators to Facilitators and Active Participants”, Annual Local Government Conference, Western University. London, November 14, 2025.
• Keynote, “Resiliency in the Age of Mis/Dis-Information”, Town of Blue Mountains & Public Library Annual Staff Session. Blue Mountains, October 24, 2025.
• Co-Presenter, “FOI Under Pressure: Practical Insights for Election-Year Transparency”, Association of Municipal Clerks, Treasurers & Managers of Ontario (AMCTO) Clerks Forum. Virtual, October 23, 2025.
• Co-Presenter, “AI in Action: Modernizing Municipal Law Departments”, Municipal Law Departments Association of Ontario (MLDAO) Fall Conference. Newmarket, October 10, 2025.
• Co-Presenter, “Bridging Boards and By-laws: Building Better Library-Municipal Partnerships”, Association of Rural and Urban Public Libraries Conference. Alliston, September 25, 2025.
• Instructor, “Authentic and Effective Community Engagement”. AMCTO Course. Virtual, September 2, 2025.
• Author, “Stratford stands strong in Ontario Court of Appeal decision on Side-Yard Squabbles”. Law360 Canada, August 7, 2025.
• Co-Presenter, “Strong Mayor Powers: Navigating the New Era”, Virtual, June 3, 2025.
• Author, “New frontier in Public Financing.” Municipal World. May 2025.
• Co-Presenter, York Region & Area Municipal Solicitors Seminar: “Effective Written Advocacy”. Newmarket, April 30, 2025.
• Moderator & Panelist, Municipal and Public Entity Risk Conference: “Effective Defence Collaboration”. Brampton, April 24, 2025.
• Chair & Presenter, Election Excellence for Municipal Clerks: “Preparing for Worst-Case Scenarios in Ontario Municipal Elections”. Virtual, April 3, 2025.
• Instructor, Association of Municipal Managers, Clerks & Treasurers of Ontario (AMCTO): Authentic and Effective Community Engagement”. Virtual, February 26, 2025.
• Speaker, Ontario Library Association Super Conference, “Power Plays and Public Purpose: Municipal Councils and Library Boards” and “Legally Leveraging AI in Public Libraries”, January 31, 2025
• Speaker, Canadian Urban Institute’s State of Canada’s Cities Summit, “Municipal Innovation: Overcoming Restraints & Seizing Opportunities”, December 6th, 2024
• Guest Lecturer, Master’s of Public Policy, Administration & Law Class, “Municipal Innovation”, York University, October 21, 2024
• Presenter, Canadian Urban Institute: “Is this the mid-size city’s moment?” Virtual, June 17, 2021.
• Presenter, AMCTO Leaders’ Forum: The Future of Tomorrows Communities, “Building the Future Public Experience for Municipal Services,” Virtual, October 9, 2020.
• Presenter, National Public Sector Conference of the Chartered Professional Accountants: “Disruptive Technologies,” Shaw Convention Centre, Ottawa, October 29, 2019.
• Keynote Address, Improved Transportation: Moving Together!, OntarioTech University, Oshawa, October 16, 2019.
• Keynote Address, Ontario Expropriations Association Spring Conference, Toronto, June 6, 2019.
• Presenter, AMCTO 2018 Municipal Finance Forum: “Public Private Partnership- Innovative Case Studies”, Toronto, December 2018.
• Presenter, University of Western Ontario’s Local Government Conference: Interrupted, “Interrupting the Status Quo: what are the roles of politicians, administration, academia, and the private sector in fostering innovation in public service”, London, November 2018.
• Presenter, TedX Collingwood: “Innovation in Local Government,” Collingwood, October 2018: https://tedxcollingwood.ca/speaker/jason-reynar/
• Presenter, Municipal Innovators Conference: “Innovating Infrastructure in Mid-Size Cities”, Calgary, September 2018.
• Presenter, AMCTO Leaders’ Forum: Managing the Municipality of the Future: “Regulating and Leveraging Business Disruptors”, Toronto, March 2018.
• Presenter, Municipal Law Departments’ Fall Workshop: “Innisfil Uber Transit Partnership: Our Insights (So Far)”, Niagara Falls, October 2017.
• Presenter, Ontario Municipal Leadership Institute Workshops: “The Legal Framework of Municipal Councils”, 2014 – 2015.
• Presenter, Canadian Bar Association’s Annual Canadian Legal Conference: “Closed Meetings”, St. John’s, Newfoundland, August 2014.
• Presenter, International Municipal Lawyers Associations Annual Conference: “Clerks Contribute: Council Closed Meetings”, San Francisco, California, September 30, 2013.
• Jason Reynar, “`Tis Right to Record in Detail? Balancing Ethical and Legal Considerations of Municipal Council Closed Sessions Minutes” (2013) 6 Municipal & Planning Law Review (5th) 181.
• Jason Reynar, “Transparent Municipal Governance: When Must a Meeting be Open?” (2011) 88 M.P.L.R. (4th) 68.
• Recipient of the International Municipal Lawyers Association’s Canadian Scholarship to present “Transparent Municipal Governance: When Must a Meeting be Open?” at its annual conference in Chicago, September 14, 2011.
• James Newland, Brian Moher & Jason Reynar, “A Touch of Dutch: Group Actions in the Netherlands”, Class Actions, Federated Press, Spring 2008.

Year of Call

Education

• Master Certificate in Municipal Leadership (2021), Schulich School of Business, York University
• M.B.A. (2017), Schulich School of Business, York University
• Accredited Director (2016), Chartered Governance Institute of Canada
• Master of Laws with Municipal Specialization (2013), Osgoode Hall Law School, York University
• Bachelor of Laws (2007), Osgoode Hall Law School, York University
• Advanced Interpersonal Mediation Certificate (2005), St. Stephen’s Community House, Toronto
• Bachelor of Arts (Honours) (2004), University of Guelph (full scholarship)