Jonathan Fleisher
Telephone: 416 860 6596
Fax: 416 644 9330
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Suite 2100, Scotia Plaza
40 King Street West
Toronto, ON
M5H 3C2

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 2013–2019 (Asset-Based Lending, Equipment Finance Law; Banking and Finance Law)
  • Canadian Legal Lexpert Directory 2012–2018 (Asset Equipment Finance/Leasing)


Call to the bar

Ontario, 1989


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