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Prior to his appointment as a judge, his Honour practised law at Montgomery, Cassels, Somers, Dutton and was a founding partner of Winkler, Filion and Wakely in Toronto. Chief Justice Winkler is the co-founding editor of The Labour Law Journal, consulting editor of Labour Arbitration Cases (Canada Law Book) co-author of Willis & Winkler on Leading Labour Cases 2010 (Canada Law Book) and editor of O'Brien's Encyclopedia of Forms - Labour Relations and Employment, Division VII (Canada Law Book).
The Honourable Warren K. Winkler retired as Chief Justice of Ontario in December 2013.