The Toronto Star recently published an article: "Inside the offshore tax scheme that left iconic Olympian Donovan Bailey owing nearly $2.3 million in unpaid taxes". ; In the article, investigative reporter Jesse McLean covered a complicated scheme to help an athlete avoid Canadian taxes in part through making a donation to a registered charity which had actually lost its registered charity status because of non-filing of the T3010 annual return. The scheme did not work.
The article notes that "According to the tax plan, Bailey's donation would flow through a complicated web of transactions before the bulk of the money would make its way back to the sprinter, tax free, through an offshore trust".
Here is an article from the Law Times on the litigation: "Judge finds lawyer negligent for advice to Olympic skier", and here is a link to the actual case: Lindsay v. Aird & Berlis LLP, 2018 ONSC 7424 (CanLII).
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Mark Blumberg is a partner at the law firm of Blumberg Segal LLP in Toronto and works almost exclusively in the areas of non-profit and charity law.