Kevin Michaels began his wrestling career in the seventh grade when he accompanied his father's high school team to a dual meet and the junior varsity's 98-pounder didn't make weight. His father asked him, "How much do you weigh?" When the response was "95 pounds," his father replied, "Good, get on the scale" and the said, "Here's my 98-pounder.” Kevin lost his first match, 2-0. The rest of the year wasn't much better as he went winless, not an auspicious beginning. Eighth grade was much better as he began to take wrestling more seriously.

His wrestling career at Sparta High School in Sparta, New Jersey, was decent. After going undefeated on the junior varsity team as a freshman, he finished second in the district as a sophomore and junior. In his senior year, he won the district title and lost in the regional finals to a returning state champion. Because only regional champions competed at the New Jersey state tournament, Michaels never had a chance to compete in the state tournament.

Michaels attended the University of Virginia on a football scholarship, lettering three years and leading the team in tackles for two years as a 200-pound linebacker. He also wrestled and won three Atlantic Coast Conference championships after finishing third as a freshman. Michaels was captain of the wrestling team and was voted UVA Outstanding Athlete as a senior. He received his bachelor's degree in speech pathology in 1973 and his master's degree in education the following year.

He began coaching football and boys gymnastics at Kellam High School in Virginia Beach, Virginia in 1976. The following year he became the head wrestling coach and continued in that role for 20 years. During his tenure he had numerous state champions and place-winners. He coached one Junior National champion and had one of his wrestlers earned NCAA Division I All-America honors for UVA.

Since leaving Kellam, Michaels has been a volunteer assistant wrestling coach at Norfolk Academy while also being a referee and member of the Southeast Wrestling Officials Association.