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Skye Capital Partners Ltd. (“Skye Capital”) is a multi-disciplinary investment group with tremendous strength and experience in a wide variety of real estate based investments with an emphasis on structured finance and real estate ownership and operation.

Through its principals and related or associated entities, Skye Capital has extensive experience in:

  • Commercial Real Estate direct investment and management

  • Real Estate and Mortgage portfolio due diligence

  • Distressed real estate work outs

  • Mortgage underwriting 

  • Real Estate Advisory, and - CMBS (Commercial Mortgage-Backed Securities) investment and management

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Robert S. Cash, J.D.

Robert is a co-founder, President and CEO of Skye Capital and its related companies.  Robert has been involved over the past 30 years in the ownership, management, development, leasing and placement of real estate opportunities in Southern Ontario with an emphasis on commercial properties, commercial debt and structured finance.  In the 1990’s Robert was very active in the acquisition, financing and successful work out of numerous high profile distressed commercial properties in the GTA. 

Robert leads Skye Capital in its initiatives and in the investigation and structuring of new opportunities, managing relationships and due diligence.

Robert has transacted business as principal with numerous high profile Canadian and US companies, has provided advisory services to a variety of companies in the real estate construction, development and brokerage fields and has provided legal services to the Province of Ontario, several municipalities and Boards of Education.  

Formerly, Robert was a partner with Thomson Rogers, Barristers & Solicitors, specializing in Real Estate, Finance and Corporate-Commercial Law.  

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Jesse Davidson

Jesse Davidson is a co-founder and Principal of Skye Capital.  He is a serial entrepreneur who has spent the last 25 years starting, acquiring, building and managing businesses primarily in the Internet, Real Estate and Finance industries.

Jesse has been instrumental in the growth and day-to-day management of Skye Capital and the Skye Mainstreet LPs.  In his capacity as a co-founder and C.O.O of Skye CMBS, Jesse was instrumental in the due diligence, vetting and acquisition of all the assets of Skye CMBS and the structuring of each of the firm’s subsidiaries and lines of business.   Through that process, he attained in-depth knowledge of each of the CMBS pools in which the firm had investments and participated in the due diligence and re underwriting of approximately 60% of the CMBS pools created in Canada on a loan-by-loan basis.  Jesse worked closely with lead mortgage servicers as one of the primary asset management contacts for Skye Capital in the firm’s role as Controlling Class Representative on Canadian Commercial Mortgages having a total value in excess of $2 Billion CAD.  

Since co-founding the Skye Mainstreet business in 2015, Jesse has been actively involved in the due diligence and acquisition of the firm’s properties and is the primary manager of the day-to-day operations of the business, including the leasing, financing, and construction management.

Jesse holds a Bachelor of Arts (Hons) degree from the University of Toronto.

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Skye Capital is about real estate

Skye Capital is a private investment vehicle created to structure, source, acquire, hold and manage structured real estate investments with an emphasis on debt, debt instruments and commercial properties.  

Our principals are each accredited professionals in complimentary fields of endeavor specialized in real estate acquisition, finance and management.  This, combined with our sophistication in securitization and the financial markets, makes us a powerful presence on the Canadian CMBS (Commercial Mortgage-Backed Securities) and commercial real estate scene.

Our Investments


From 2009 to 2018 Skye Capital was instrumental in acquiring and managing in excess of $300 MM of Canadian CMBS securities and was Controlling Class Representative on more than $2.0 B of Canadian Commercial Mortgages. 


Our portfolio of CMBS investments has included tranches throughout the CMBS capital stack with an emphasis on B-Pieces including first loss tranches and B-Notes.   By 2018, all of Skye’s CMBS investments had successfully matured without suffering any material losses throughout the portfolio.

Skye CMBS Successes

  • Skye Capital is one of the first non Qualified Institutional Buyer(s) in Canada to have successfully acquired a portfolio of B-Notes with rating agency confirmations

  • Skye Capital has received rating agency confirmations from each of S&P, Moody’s and DBRS

  • Skye Capital successfully purchased a subsidiary of JPMorgan Chase that is the issuer of the only CMBS CDO created in Canada – Mach One 2005-CDN1, ULC

  • Skye Capital successfully received Canadian Competition Bureau approval to proceed with the acquisition of the Mach One 2005-CDN1, ULC CDO

  • Skye Capital has invested in more than 35% of the CMBS pools created in Canada

  • Skye Capital has conducted extensive due diligence and re underwritten mortgage by mortgage more than 60% of the CMBS pools created in Canada

Skye Mainstreet

From 2015 to the present, Skye's attention has been focused on acquiring and managing main street retail properties in prime Toronto locations and has assembled a portfolio of assets valued at approximately $55MM.   Skye is continually looking to grow its portfolio in this asset class and plans to ramp up its expansion in the coming years.  

The primary objective of the Skye Mainstreet business is to assemble and continually grow a portfolio of high quality, well located neighborhood commercial real estate primarily along main thoroughfares in the City of Toronto focusing on a few prominent retail nodes near significant redevelopment projects (Yonge Street, Riverdale, Leslieville, Bloor Yorkville, St. Clair and Bathurst and others).   We are constantly leveraging our considerable experience and expertise to source, evaluate, finance, lease and manage outstanding main street commercial real estate opportunities and to drive value through greater skill and efficiencies and ultimately seek exits through refinancing and redevelopment opportunities.  We predominantly target properties along key commercial nodes in the Greater Toronto Area and will make every effort to assemble properties to take advantage of efficiencies and with a view to future redevelopment potential. Assemblies are not crucial to our plan. We are content to have a presence on future development blocks to be able to participate in future opportunities as they might arise.






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121 Richmond Street, Suite 1000

Toronto, Ontario, Canada, M5H 2K1

Tel: 416-214-4943

Fax: 416-367-9996


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