"Every man is entitled, if he can, to order his affairs so that the tax attaching under the appropriate Acts is less than it otherwise would be".

House of Lords
Inland Revenue Commissioners vs. Duke of Westminister


Our team has substantial investment banking, transaction structuring and negotiating experience with major firms, including in-depth legal tax and accounting structuring expertise.

We act as arrangers by bringing together investors with borrowers/lessees in mutually beneficial financing transactions. We are adept at sourcing tax-motivated investors to provide the equity component of leveraged transactions. In addition, we arrange debt financing often on a limited recourse basis on behalf of borrowers/lessees who benefit from the novel transaction structures that we have developed.

One of the principals of GSS designed and implemented the sale and leaseback transaction structure that was recently the subject of a favourable decision by the Supreme Court of Canada. The case entitled Canada Trustco Mortgage Co. V. Canada is now the leading precedent in Canada on the general anti-avoidance rule and provides support for parties considering tax-based leasing transactions. This case resulted in a change of law in the March 2010 federal budget that adversely affected cross border leasing, subject to grandfathering protection for the taxpayer in question.


Our structured solutions include:

  • Monetization of tax losses for Canadian companies wishing to extract value for an otherwise underperforming asset;
  • Tax efficient options for Canadian companies seeking to access the U.S. private placement market that can result in lower financing costs;
  • Solutions for taxable Canadian companies with significant unencumbered capital assets who wish to maximize their Canadian tax deferral opportunities;
  • Domestic Canadian tax leases for qualifying assets;
  • Customized asset-based financing transactions for aircraft and rail assets, as well as public infrastructure, power and energy facilities

Recent Mandates

Advised a Canadian family office in connection with various private equity investments in the US.

Established an international aircraft leasing platform in Ireland with secured financing provided by Export Development Canada in the amount of US $50 million.

Advised on a US $25 million equity investment in connection with a start-up aircraft leasing company based in Dublin.

$100 million monetization transaction – we structured and arranged a transaction involving a public biotech company that was completed after the March 2010 federal budget

$190 million lossco transaction – we arranged a reverse takeover involving an income fund that was completed prior to the March 2010 federal budget

$150 million helicopter acquisition – we advised a provincially mandated medical transport company on the purchase and related vendor financing of a new fleet of EMS helicopters



Explore the Possibilities

Contact us and let us explore how we may be able to bridge the gap from traditional investment banking to more exotic structures.

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