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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.

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ABOUT US

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

ABOUT US
OUR INVESTMENTS
SKYE MANSTREET

OUR INVESTMENTS

SKYE MAINSTREET

 

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.  

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SKYE CMBS

 

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

SKYE CMBS
MANAGEMENT

MANAGEMENT

Construction Plans
Architectural Modelling

Robert S. Cash, J.D.

Robert is a Co-Founder and Principal of Skye Capital Partners.  Robert has been involved over the past 35 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 was instrumental in founding Skye Mainstreet and shaping its investment strategy, and continues to provide strategic advice and direction across Skye Capital's businesses.

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 Partners. He has spent the last 30 years founding, acquiring, and operating businesses in real estate, finance, and technology.


Jesse co-founded Skye Mainstreet in 2015 and leads the firm's day-to-day operations across its multiple partnerships and investments, with direct responsibility for acquisitions, leasing, financing, and construction. The Skye Mainstreet portfolio has been built one asset at a time, in pursuit of a thesis that combines disciplined value investing with patient long-term growth.


Earlier in his career, Jesse was Co-Founder and Chief Operating Officer of Skye CMBS, which acquired Canadian commercial mortgage-backed securities (CMBS) during the 2008–2010 financial crisis at deep discounts to face value. He participated in the re-underwriting of approximately 60% of the CMBS pools ever created in Canada, on a loan-by-loan basis, and the firm served as Controlling Class Representative on Canadian commercial mortgages with a total value in excess of $2 Billion CAD. The portfolio matured between 2015 and 2018 with effectively no credit losses.


Jesse holds a Bachelor of Arts (Honours) from the University of Toronto. He is a student of the value and growth investing traditions, and has worked to connect Skye's investment approach to their principles — adapting them to the firm's specific strategy and asset class, and helping to develop the firm's investment philosophy along the way.

CONTACT

CONTACT

HEAD OFFICE

121 Richmond Street West 

Suite 1000

Toronto, Ontario

Canada, M5H 2K1

E: info@skyecapital.com

T: 416-214-4943

F: 416-367-9996

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Copyright © 2026 by Skye Capital Partners Ltd. and Eglinton Tarlton Limited Partnership. All rights reserved.
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