Willis Edward (Bill) O'Leary was born in Vulcan, Alberta and raised outside Edmonton and in Calgary, which he considers home. He grew up playing hockey in Calgary and his talent would determine the early years of his life. He was invited in 1949 to the New York Rangers prospect camp. While never playing for the NY Rangers, O'Leary did receive a scholarship to play hockey at the University of Denver, where he graduated with a degree in Business Administration in 1953. He planned to continue studying at the University of Denver in pursuit of a law degree, but instead played a season of semi-professional hockey in England.
He returned a year of hockey to work for the Canadian Gulf Oil Company in Calgary. He earned money in the employee relations department and having saved enough, applied for law school at the University of British Columbia, attracted by the school's excellent reputation. He graduated from UBC in 1962, and attended Harvard Law School for a year after graduation. He returned to Canada and secured articles at Fenerty, Fenerty, McGillivray, Robertson, Prowse, Brennan & Fraser, which would become Fraser Milner Casgrain LLP. After starting his career under R. L. Fenerty QC, O'Leary decided to hang out his own shingle with two colleagues, and formed the firm of Lutz, Westerberg & O'Leary. He focuses on general law and insurance litigation, and helped to grow the firm to 12 lawyers.
During his professional career, O'Leary was also helped administer the Law Society of Alberta's Bar Admission Course. He helped found the Legal Education Society of Alberta and was it's President for two years.
In 1984, Bill O'Leary was appointed to the Alberta Court of Queen's Bench, and ten years later raised to the Alberta Court of Appeal. He retired from the bench in 2007, and continues to work as a mediator and arbitrator.