Donovan Bailey award received Canada's Walk of Fame
Post-retirement
After racing, Bailey started his own company called DBX Sport Management which helps amateur athletes find a way to promote themselves.  He also started a sport injury clinic in Oakville, Ontario.
He has been inducted into Canada's Sports Hall of Fame twice: in 2004 as an individual, and in 2008 as part of the 1996 Summer Olympics 4 × 100 relay team.In August 2008 Bailey began work as a track commentator for CBC Television at the 2008 Summer Olympics. He estimated that had Usain Bolt not slowed down near the end of the 100m dash (which he still won in record time), he could have set a time of 9.55 seconds. He returned as the track analyst for CBC's coverage of the 2016 Summer Olympics.In 2010, Bailey was one of the recipients of the Top 25 Canadian Immigrant Awards presented by Canadian Immigrant Magazine.In 2014, Bailey pleaded guilty to a drinking and driving charge from 2012. This was the third driving-related incident for Bailey. In 1998 he crashed his car into a concrete utility pole and was fined $200 for failing to report an accident. In 2001, Bailey was fined $975 for driving 200 km/h on a 100 km/h road in Toronto.In 2016, he was made a member of the Order of Ontario. In 2017, Canada's Walk of Fame honoured him with a star.In 2018, it was reported that Bailey had provided his entire athlete's trust of $3.75 million to Aird & Berlis lawyer Stuart Bollefer, who invested it in what was determined to be a tax evasion scheme by the Canadian government. Bailey lost the full amount due to the scheme, however the courts ordered Aird & Berlis to pay all outstanding taxes due to their negligence.In 2022, Bailey was named an officer to the Order of Canada.
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