Gray was born at the University of Kansas Medical Center in Kansas City, Kansas and raised in Kansas City, Kansas. Because of his stature, Gray was affectionately referred to in his hometown as "Hugie".
Gray attended Sumner High School where he played basketball all four years and football through his junior year. During Gray’s junior football season, he broke his leg and chose not to return for his senior football season.
During his senior year at Sumner, Gray led the Spartans to an undefeated season and the 1969 Kansas Class 4 state basketball championship. In the state title game against McPherson High School, Gray totaled 24 points and 22 rebounds. Gray’s high school coach Roy Flook told the Kansas City Star that college coaches told him that “Leonard is the top prospect in the country”.

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