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==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 Γ 100 relay team.<ref>{{Cite web|url=https://www.tsn.ca/other_sports/story/?id=237621&lid=headline&lpos=topStory_main |title=Yzerman, Lewis among Canada's Sports Hall of Fame inductees|publisher=[[The Sports Network]]|date=2008-05-13 |access-date=2008-05-13}}</ref> In August 2008 Bailey began work as a track commentator for [[CBC Television]] at the [[2008 Summer Olympics]].<ref>CBC Television, ''Olympic Morning'', 16 August 2008</ref> He estimated that had [[Usain Bolt]] not slowed down near the end of the 100 m dash (which he still won in record time), he could have set a time of 9.55 seconds.<ref>''New York Times'', [https://www.nytimes.com/2008/08/19/sports/olympics/19sprint.html?pagewanted=print Sprinters Marvel at Bolt and Are Sure That His Best Is Yet to Come], CHRISTOPHER CLAREY, August 19, 2008 (accessed 19 August 2008)</ref> He returned as the track analyst for CBC's coverage of the [[2016 Summer Olympics]].<ref>{{cite web|title=CBC Media Centre - Press Releases - CBC ANNOUNCES ALL-STAR ROSTER OF EXPERT COMMENTATORS AND ANALYSTS FOR ITS COVERAGE OF THE RIO 2016 OLYMPIC GAMES|url=http://www.cbc.ca/mediacentre/cbc-announces-all-star-roster-of-expert-commentators-and-analysts-for-its-coverage-of-the-rio-2016-o.html|website=www.cbc.ca|access-date=14 September 2016}}</ref> In 2010, Bailey was one of the recipients of the Top 25 Canadian Immigrant Awards presented by [[Canadian immigrant magazine|Canadian Immigrant Magazine]].<ref>{{Cite web|title=Canada's Top 25 Immigrants 2010|url=https://canadianimmigrant.ca/canadas-top-25-immigrants/canadas-top-25-immigrants-2010|access-date=2021-06-18|website=Canadian Immigrant|language=en-US}}</ref> 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.<ref>{{cite web|url=https://www.thestar.com/news/crime/2014/08/26/donovan_bailey_pleads_guilty_to_drinking_and_driving_charge.html|title=Donovan Bailey pleads guilty to drinking and driving charge|publisher=The Toronto Star|date=2014-08-26|accessdate=2022-06-29}}</ref> In 2016, he was made a member of the [[Order of Ontario]].<ref>{{cite web |url= https://news.ontario.ca/mci/en/2016/12/the-2016-appointees-to-the-order-of-ontario.html |title= The 2016 Appointees to the Order of Ontario |date= December 14, 2016 |agency= Ministry of Citizenship and Immigration}}</ref> In 2017, [[Canada's Walk of Fame]] honoured him with a star.<ref>{{cite web |url=https://www.sportsnet.ca/olympics/canadas-walk-fame-honour-sprinter-donovan-bailey/ |title=Canada's Walk of Fame to honour sprinter Donovan Bailey|publisher=Sports Net|date=2017-11-15|accessdate=2021-08-06}}</ref><ref>{{cite web |url=https://www.kelownanow.com/news/news/National_News/Donovan_Bailey_1_of_6_Canadians_inducted_into_Walk_of_Fame/|title=Donovan Bailey 1 of 6 Canadians inducted into Walk of Fame|first=Liz|last=Brown|publisher=Kelowna Now|date=2017-10-26|accessdate=2021-08-06}}</ref><ref>{{cite web |url=https://www.cbc.ca/sports/olympics/trackandfield/donovan-bailey-walk-fame-1.4404649|title=Donovan Bailey 'humbled' by Walk of Fame star|publisher=CBC News|date=2017-11-15|accessdate=2021-08-06}}</ref> 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.<ref>{{cite web|url=https://www.thestar.com/news/investigations/2018/06/11/inside-the-offshore-tax-scheme-that-left-iconic-olympian-donovan-bailey-owing-nearly-23-million-in-unpaid-taxes.html|title=Inside the offshore tax scheme that left iconic Olympian Donovan Bailey owing nearly $2.3 million in unpaid taxes|first=Jesse|last=McLean|publisher=The Toronto Star|date=2018-06-11|accessdate=2021-08-06}}</ref> In 2022, Bailey was named an officer to the [[Order of Canada]].<ref name="gg.ca" />
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