top of page

SKYE CAPITAL PARTNERS is in the business of carefully identifying exceptional real estate opportunities in all market conditions.  We employ our considerable expertise and resources to source opportunities, undertake due diligence, execute deals and manage assets to drive outperform returns on capital.



Skye Capital is about real estate.

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

A common thread throughout each of our many ventures is a focus on achieving outperform returns through innovative deals in all stages of the economic cycle. 

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

  • Commercial Real Estate direct investment, development and management

  • Real Estate and Mortgage portfolio due diligence and management

  • Distressed real estate work-outs

  • Mortgage underwriting 

  • Structured Finance

  • Real Estate Advisory, and

  • CMBS (Commercial Mortgage-Backed Securities) investment and management





From 2015 to the present, Skye's attention has been focused on acquiring, redeveloping and managing high profile and iconic main street retail properties in prime Toronto locations.   Our goal is to leverage our expertise in real estate acquisition, land assembly, finance and redevelopment to create great retail and office experiences and drive outperform returns on capital.  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 continue to assemble and grow our portfolio of high quality, neighborhood commercial real estate located primarily along main thoroughfares in the City of Toronto.  We focus our investment efforts on a few prominent retail nodes near modes of transportation and significant redevelopment projects. We source, evaluate, finance, lease and manage outstanding main street commercial real estate opportunities and drive value through greater skill and efficiencies and we ultimately seek exits through refinancing and redevelopment opportunities.  

Screen Shot 2021-02-06 at 16.01.49.png



From 2008 to 2010 Skye CMBS became one of the largest non-Bank owned CMBS (Commercial Mortgage-Backed Securities) B-Piece buyers and managers in Canada managing in excess of $300 MM of Canadian CMBS securities.  Skye CMBS invested in more than 35% of all Canadian CMBS deals, acquired rating agency approvals as a Non-Qualified Institutional Buyer to acquire B-Notes and acquired the issuer of the only CMBS CDO created in Canada. 

In 2008, Skye CMBS identified the opportunity to take advantage of the US credit crunch to acquire performing Canadian CMBS B-Pieces from US vendors at significant discounts to face value. Skye assembled a skilled team of real estate, legal, accounting and appraisal specialists to evaluate buying opportunities and to execute on deals. By 2011, Skye had acquired a significant private portfolio and had become Control Class Representative on more than $2 Billion 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 CMBS 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 CMBS has received rating agency confirmations from each of S&P, Moody’s and DBRS

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

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

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

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



Construction Plans
Architectural Modelling

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 governments and related agencies. 


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

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.  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.

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.

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





121 Richmond Street West 

Suite 1000

Toronto, Ontario

Canada, M5H 2K1


T: 416-214-4943

F: 416-367-9996

Thanks for your message. We'll be in touch shortly.

bottom of page