Son of M. Grattan O'Leary and Mary McKenna of Ottawa, ON. Pilot Officer O'Leary was considered extremely bright, according to his Air Force Interview Report. His father was the Local Editor of the Ottawa Journal. His hobbies included recreational sports (hockey, golf, softball, football and ping pong) and playing the piano. Attended St. Pat's College's Accounting Program prior to enlisting in 1941.
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