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Two-time Olympic champion Donovan Bailey involved in tax scandal

One of the greatest sprinters of all time reportedly owed a staggering $2.3 million in unpaid taxes

Donovan Bailey
Donovan Bailey
Donovan Bailey celebrates winning 100m gold at the 1996 Olympics. Photo: Canadian Olympic Committee.

One of the greatest sprinters of all time reportedly owed a staggering $2.3 million in unpaid taxes. 

Donovan Bailey is a two-time Olympic champion, and a two-time world record holder. Beyond those accolades, he is also an eight-time Canadian champion, and three-time world champion. Bailey’s main event was the 100m.

Bailey’s funds were shielded from taxes in an athletic trust during his professional athletic career, but upon his retirement, he was forced to remove the funds from their protected state. Once Bailey’s money was removed from his athletic trust account, he hired a tax lawyer to provide him with a tax strategy.

Bailey worked with tax lawyer Stuart Bollefer of tax firm Aird & Berlis.

He allegedly gave $3.75 million to charity, under the assumption that the money would make its way back into his pocket.

Bollefer reportedly promoted a tax plan that sent Bailey’s money through a complicated series of transactions via an off-shore trust, before coming back to him.

The CRA began investigating Bailey’s tax returns around 2010. His 2006 and 2007 tax returns reportedly claimed millions in charitable donations. 

By October of 2017, following years of investigation, Bailey began to answer questions about his personal finances. At that time, he owed a reported $2.3 million in taxes, but only had roughly $3,000 worth of belongings, along with a share in a property in Jamaica. 

Bailey posted a statement from his lawyer on Tuesday. The Twitter post stated that, “He along with other high net worth individuals invested in good faith in a tax plan with professional advice. This resulted in a significant tax liability to the CRA which was resolved.” 


In late 2017, Bailey and the CRA came to an agreement where the CRA was to be paid $750,000 of the $2.3 million owed, based on the poor professional advice that Bailey received. 

According to Bailey’s Twitter account, he’s writing a book and filming “The Bailey Project,” both due out this fall. He also works currently as a sports analyst and commentator.


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