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Leonard qualified as a Solicitor in 1980, having studied at Queen's University Belfast and the Institute of Professional legal studies. He was appointed as a partner at John McKee Solicitors in 1983 and Senior Partner in 2008 . Throughout his time with the firm he has been involved in dealing with litigation and employment matters with the major proportion of his work having been in Defence Litigation, dealing with all types of claims. Leonard specialises in high value catastrophic claims arising mainly out of road traffic, farming and construction site accidents. He also advises insurers in relation to indemnity issues and policy disputes and Health and Safety matters.
In May 1998, Leonard was appointed as a Deputy County Court Judge. He is also an occasional Tutor at the Institute of Professional Legal Studies and on the Law Society of Northern Ireland Advanced Advocacy Course.