From 2005 until October 2009, he served as the Commissioner & Chairman of Canada's only pro soccer league, the Canadian Soccer League Achievements during his tenure included affiliations with Canada's governing body, the Canadian Soccer Association, as well as with Canada's top two Pro Teams Toronto FC and the Montreal Impact and establishment of a television contract with Rogers TV, and a Reserve Divisions.
Association football | association football | football (soccer) | Forward (association football) | Goalkeeper (association football) | Defender (association football) | Football (soccer) | Canadian Broadcasting Corporation | National Basketball Association | Canadian Pacific Railway | Major League Soccer | American Association for the Advancement of Science | Association of Tennis Professionals | American Library Association | World Boxing Association | National Collegiate Athletic Association | United States men's national soccer team | Royal Canadian Navy | Royal Canadian Air Force | Canadian Football League | American Association | American Heart Association | Canadian Forces | National Association of Intercollegiate Athletics | Canadian National Railway | National Rifle Association | International Development Association | Royal Canadian Mounted Police | National Association for the Advancement of Colored People | Canadian dollar |
On 1 June 2011, it was announced by Umbro that Jackson had signed an endorsement deal following the new partnership between the English sportswear company and the Canadian Soccer Association, making Jackson one of the few Canadian players to have an endorsement deal.