From 1976 to 2008 he was a partner with the law firm of Ruby & Edwardh with Marlys Edwardh. Since 2007, he has been a partner with the law firm of Ruby Shiller Chan Hasan in Toronto, Ontario. In 1991, Ruby was part of the legal team used by the Church of Scientology to defend itself and nine of its members who were on trial for stealing documents concerning Scientology from the Ontario Ministry of the Attorney General, the Canadian Mental Health Association, two police forces and other institutions. The case stemmed from a surprise raid of the Church of Scientology's Toronto headquarters in 1983 by more than a hundred policeman who seized an estimated 250,000 documents over the course of two days. Legal maneuvers used by Ruby delayed the case for many years and he later unsuccessfully attempted to get the case dismissed because of "unreasonable delay." On June 25, 1992, seven church members were convicted for operations against the Ontario Provincial Police, the Ontario Ministry of the Attorney General and the Royal Canadian Mounted Police. The Church of Scientology itself was convicted on two counts of breach of the public trust and was ordered to pay a $250,000 fine. In 2006, Ruby was made a Member of the Order of Canada. In late 2005, Ruby became the acting Treasurer, or elected head, of the Law Society of Upper Canada, the body responsible for regulating the Province of Ontario. On February 23, 2006, however, Ruby was defeated in a special election and ceased to be Treasurer. In 2012, Ruby represented a plaintiff who attempted to oust Mayor Rob Ford of Toronto in a high-profile conflict of interest case, which the plaintiff and Ruby won. The mayor subsequently launched an appeal. On January 25, 2012 Mayor Rob Ford won the appeal and remained in office. In 2013, Ruby successfully argued for the former Ontario Deputy Minister of Education Ben Levin's release on $100,000 bail. Ruby told reporters " is a man who has made enormous contributions to the educational system in this province, and indeed with changes that have been copied around the world, And I intend to work very hard to see that he shall be innocent." Ben Levin was charged with one count of making child pornography, one count of counselling to commit an indictable offence, 2 counts of distributing child pornography and agreeing to, or arranging, a sexual offence against a child under 16. Levin was eventually sentenced to three years in prison on the aforementioned charges.
Personal life
He is married to Madam Justice Harriet Sachs of the Superior Court of Justice of Ontario. Clayton Ruby's father, Louis Ruby, was publisher of Flash Weekly a crusading Toronto tabloid and scandal sheet that ran from the late 1930s until the 1970s.
Clients
Some of Ruby's high-profile clients have been the following:
