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t: 416 860 6596
f: 416 644 9330
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Suite 2100, Scotia Plaza
40 King Street West
Toronto, ON  M5H 3C2

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Year of Call

Ontario, 1989


J.D., University of Toronto, 1987

MBA, Clarkson University, 1982

B.Comm., University of Toronto, 1980

Jonathan Fleisher

Jonathan Fleisher* is a partner in the Financial Services and Business Law Groups.

His financial services practice focuses on the commercial finance industry with a particular emphasis on innovative cross-border transactions and equipment and asset finance, where he has been recognized as a leading lawyer by the Canadian Legal Lexpert Directory and Best Lawyers. He has particular expertise assisting public and private US commercial finance companies with both establishing operations in Canada and purchasing and selling finance and lease companies, providing both legal and practical business advice. Jonathan's work in the automotive sector is focused on structured finance, securitization and commercial and consumer leasing issues. His experience also extends to all forms of debt finance including sub-debt, venture financings, convertible debt, tranche b debt and asset-based lending.

Jonathan’s exposure to commercial finance provides him with a unique insight in acting for both debtors and creditors in financial restructuring. His solicitor-focused restructuring practice focuses on strategic planning within an insolvency context. When acting for a creditor, Jonathan provides practical advice on how to maximize returns without exposing the creditor to enhanced liability. For debtors, his advice includes structuring debt investments, advising directors on how to minimize personal liability and developing plans to allow entities to utilize insolvency legislation to assist a company’s recovery.

Jonathan is an avid lecturer and writer on both a domestic and international level. Typically he speaks about six times per year at both business and legal conferences. He is also a prolific writer on topics related to equipment finance and cross-border transactions. Jonathan is the legal editor for Fleet Digest magazine and has completed both the Equipment Finance and Subordinated Debt chapters for Canadian Forms & Precedents. He has also drafted specific guides for US lenders expanding operations to Canada.

His work in this area includes:

  • Acting for CIT Financial Ltd. in an equipment based revolving loan to Bauer- Pileco for assets located in Canada and the US
  • Acting for a private equipment finance company in the sale of the business
  • Representing Hitachi Capital America Corp in their expansion into Canada through their subsidiary Hitachi Capital Canada Corp. and the development of a marketing and services agreement between Hitachi Canada and CLE Leasing Enterprise Ltd.
  • Acting for a multi-national equipment finance company, as borrower, in a US$300 million syndicated credit facility
  • Advising lenders, arrangers and borrowers on lease and debt financings of railcars
  • Developing and executing private securitization structures
  • Securitizing auto portfolios of cross-Canada dealers
  • Handling a private securitization of equipment finance portfolios in nine figure transactions
  • Representing international and domestic banks and commercial finance companies as both purchasers and sellers in nine figure portfolio transactions
  • Representing Banks in purchasing all of the assets of a private leasing company
  • Acting for a multinational commercial finance company on a significant insolvency of one of its borrowers
  • Handling a joint venture and program structures between top 10 international banks and the world’s largest software and equipment providers
  • Developing commercial finance precedents and procedures for newly established Canadian entities
  • Acting for both purchasers and sellers of commercial finance companies

Jonathan sits on the board of a number of his clients.

The corporate side of Jonathan’s practice focuses on all aspects of corporate law, including mergers and acquisitions, finance and strategic advice. He has a particular expertise with both finance companies and mid-sized technology companies assisting them from start-up to their eventual take-out strategy. He is able to provide legal and business advice gained from his pre-legal career.

*denotes Professional Corporation

asset based

  • Martindale-Hubbell, AV Preeminent™ rating
  • The Best Lawyers in Canada 2013–2020 (Asset-Based Lending, Equipment Finance; Banking and Finance)
  • Canadian Legal Lexpert Directory 2012–2019 (Asset Equipment Finance/Leasing)


  • American College of Commercial Finance Lawyers, Board of Regents
  • Canadian Finance and Leasing Association, Director
  • Equipment Leasing and Finance Association, Committee Member (Legal)
  • Association for Corporate Growth
  • Canadian Bar Association
  • Ontario Bar Association
Publications, Newsletters and Articles Publications, Newsletters and Articles

Ontario Joins the 21st Century by Introducing Electronic Chattel Paper

Good News for Auto Lessors in Ontario: Motor Vehicles Used for Ride Sharing May be Covered by the Vicarious Liability Cap

Catching Up: Ontario Introduces Rules to Enhance Securitization of Electronic Finance Contracts

Solar Power Update: SCC Leave to Appeal Refused

What's Old is New Again – Interest Rate Decision in Ontario is What Lenders Expect

Personal Property Security Act and Repair Storage Lien Act Priorities

Lessons Learned - Lesson One Supplement: Get the Name Right on the Financing Statement

Security Interests in Railcars: A Canadian Overview

Reliance on Collateral Descriptions Reinstated and New Hope that Section 7 of the Personal Property Security Act (Ontario) (where to register) Will be Proclaimed into Force

Purchasers of Chattel Paper and Instruments

The Business of Asset Finance - A Primer for Lawyers

Personal Property IJARAH Sukuk's Canadian Legal Issues and the Leasing Market

Purchase-Money Security Interests: Cross-collateralizing without waivers

The Transition to New Rules for Pre-Authorized Payment Plans

Purchasers of Chattel Paper & Instruments

Restructuring and Insolvency Group e-COMMUNIQUE - October 2009

Canadian Insolvency Law Amendments: Focus for Equipment Financiers

The Canadian Equipment Finance Environment

Financial Services Group e-lert - May 2009

Changes to Canada’s Income Tax Act and Impact on Equipment Finance

Federal Government Releases Consultation Paper on Leasing Framework

Commercial Lessors and the New Motor Vehicle Sales and Dealership Regime in Ontario

Ontario Motor Vehicle Dealer's Act 2002 Implementation Delayed Until January 1, 2010

Motor Vehicle Dealers Act Coming into Effect April 1, 2009
Equipment Financiers Must Take Action

Conferences, Speaking Engagements, Events Conferences, Speaking Engagements, Events