Gary grew up in Eagle River, Alaska, and graduated from the University of Texas at Austin. Gary received his Juris Doctor from the University of San Diego in 1990. Gary began his legal career as a deputy district attorney in the Denver Metro Area, and is a former President of the Adams County Bar Association. During his 25 years of practice, Gary has conducted over 400 jury trials in federal and state courts all across Colorado.

He has argued before the U.S. Court of Appeals for the 10th Circuit, and regularly appears in Federal District Court for the District of Colorado. Gary has fought countless cases before the Colorado Court of Appeals, and was solely instrumental in securing certain basic rights for parolees in the landmark case of Madison v Department of Corrections – which Gary litigated before the Colorado Supreme Court in 2004.