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Gary was born in 1953 and raised in Great Falls, Montana. He attended the University of Montana and obtained a B.A. in Economics and Political Science in 1975. He then attended the University of Montana School of Law where he obtained his JD degree in 1978. He was a Deputy Cascade County Attorney from 1978-1979. Gary was President of the Cascade County Bar Association in 2005.
Gary has been an associate professor of evidence and criminal procedure at the College of Great Falls (1979-1981). He has also been a frequent lecturer at the University of Montana School of Law and other continuing legal education seminars on the issue of insurance.