Jonathan D. Gaynor
Partner | Philadelphia
Jonathan D. Gaynor

Jonathan Gaynor is a partner in Dechert's global finance practice, focusing on innovative structured finance solutions for clients across a variety of asset classes and collateral types. Mr. Gaynor represents investment banks, commercial banks, financial institutions, private equity funds, hedge funds, life insurance companies, REITs and institutional investors in complex commercial mortgage loan and securitization transactions.

In the commercial real estate finance arena, Mr. Gaynor advises buyers and sellers on repurchase facilities, warehouse loans and other structured finance products. His experience spans traditional repurchase facilities, loan-on-loan financings, cross-border facilities and hybrid loan/securitizations, financing performing assets, non-performing and distressed assets, real estate owned (REO) assets and intracompany loans post-foreclosure.

Mr. Gaynor is a recognized leader in single-family rental (SFR) securitization and finance, representing both issuers and underwriters in programmatic issuances as well as bespoke structures tailored to client-specific capital and regulatory needs.

Mr. Gaynor co-hosts the Dechert 4 Real Podcast, which explores current issues and trends impacting real estate finance transactions. In Dechert’s Philadelphia office, he serves as co-head of the landlord-tenant pro bono program and is a member of the hiring committee. Mr. Gaynor’s commitment to innovation has earned him recognition as a Dechert Star Legal Innovator and he is a graduate of the firm’s Innovation Certificate Program. Mr. Gaynor is recognized by The Legal 500 for his work in real estate finance.

  • Led more than 50 SFR securitization transactions representing both issuers and underwriters, with an aggregate value exceeding $20 billion
  • Developed and implemented multiple market-moving features for SFR securitizations that improved attachment points and transaction efficiency, including payment-in-kind features, bond exchange mechanics, trigger bond structures and collateral release improvements
  • Advised on the structuring of a direct issuance of SFR-backed securities designed to achieve rated notes for insurance company investors without regulatory drag
  • Represented multiple financial institutions in establishing and maintaining their programmatic commercial mortgage loan repurchase facility platforms
  • Led development of hybrid loan/securitization structures to provide liquidity alternatives when traditional capital markets were inaccessible
  • Represented financial institutions in cross-border repurchase facilities involving loan assets in Europe and Australia
  • Structured swing-line repurchase facility arrangements for several financial institutions to provide flexible, short-term financing solutions
  • Represented a residential transition loan lender in connection with seasoning and term repurchase facilities for their RTL, DSCR loan and SFR lending program
  • Advised a commercial real estate debt fund on a bespoke upper-tier hybrid financing structure allowing international sovereign wealth fund investors to participate in levered returns from warehouse facilities
  • Represented commercial real estate lenders on repurchase facilities for non-performing loans and REO assets following foreclosure
  • Advised debt funds on restructuring and workout strategies for distressed assets within multiple warehouse facilities during market disruption
  • Led development of AI-based solution to efficiently review over 3,000 contracts for a major financial institution’s LIBOR transition
Services
    • University of Pennsylvania, B.A., 2005
    • University of Pennsylvania, M.A., 2006
    • University of Notre Dame Law School, J.D., 2013, cum laude, Editor-in-Chief of the Journal of College and University Law, 2012 (Vol. 39); Oralist for the New York Nationals Moot Court Team
    • Pennsylvania

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