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James O'Leary has a wealth of experience in the legal field. James began their career as a Junior Counsel at the Law Library in Dublin in 1991, where they worked until 1999. In 2000, they joined Trinity Mirror Group PLC as a Legal Adviser, and shortly after, they also took on the role of Head of the Legal Department for Ireland at Reach plc. Their tenure in both positions is ongoing.

James O'Leary attended The Honorable Society of King's Inns and University College Dublin, but no specific degree or field of study is mentioned.