Jonathan David Gaynor

JON GAYNOR represents lenders and borrowers in commercial real estate finance, with a focus on repurchase and warehouse facilities, loan-on-loan and note-on-note financings, and other back-leverage arrangements for commercial mortgage loans and CRE securities. His clients include banks and other financial institutions, mortgage REITs, private credit and real estate debt funds, and insurance companies. Jon's work on both sides of these financings gives him a broad perspective on the market and a clear view of how terms are evolving.

Jon has negotiated hundreds of repurchase, warehouse, and loan-on-loan facilities with aggregate capacity of more than US$50 billion. He advises banks and borrowers on loan-on-loan and note-on-note financing on a programmatic basis, and he develops bespoke financing structures around a client’s capital, credit, and regulatory objectives. He has designed swing-line repurchase facilities and hybrid loan/securitization structures that provided liquidity when the capital markets were closed, and he helps debt funds structure investments that isolate the levered returns generated by back-leverage facilities.

Jon’s matters involve loans secured by multifamily, office, industrial, retail, hospitality, self-storage, and data center properties, as well as construction loans, single-family rental (SFR) assets, and residential transition loans. He helps his clients finance performing, sub-performing, non-performing, and distressed loans and REO assets, including through cross-border facilities with loan assets in Europe and Australia. He has also represented banks and debt funds in restructuring and working out repurchase facilities and the related underlying loans during periods of market disruption.

Jon also represents issuers and underwriters in SFR finance and securitization, in both programmatic and bespoke transactions. He has led more than 50 SFR securitizations totaling more than US$20 billion and developed several market-moving features that improved attachment points and transaction efficiency, including payment-in-kind features, bond exchange mechanics, trigger bond structures, and collateral release improvements.

Jon has represented both lenders and borrowers in each of the following:

• Repurchase and warehouse facilities for commercial mortgage loans across all major property types, for banks, insurance companies, mortgage REITs and real estate debt funds.
• Loan-on-loan, note-on-note and participation financings, including for data center, hospitality, self-storage and construction loans.
• Cross-border repurchase facilities for commercial mortgage loans in the U.K., continental Europe and Australia, including multi-currency facilities.
• Repurchase facilities for non-performing loans and REO assets.
• Seasoning and term repurchase facilities for residential transition loan (RTL), DSCR and SFR lending programs.
• Swing-line repurchase facilities that provide flexible, short-term financing.
• Hybrid loan/securitization structures, term-out facilities and private CRE CLO transactions.
• Restructurings and workouts of repurchase facilities and the underlying loans.

Other representative matters include:

• Real estate debt funds in bespoke upper-tier structures that isolate for specific investors the levered returns generated by financings.
• Issuers and underwriters in programmatic and bespoke SFR securitizations.
• An SFR issuer in a direct issuance of SFR-backed securities structured to achieve rated notes for insurance company investors without regulatory drag.
• A major financial institution in developing, in 2018, a machine learning-based solution to review more than 3,000 contracts for its LIBOR transition.

The above matters were handled prior to joining Sidley.

• Defends low-income tenants in eviction proceedings in Philadelphia Municipal Court.