Gary Calip graduated from Hobart High school in 1974. He attended Southwestern University where he played football and baseball, majoring in education. He later attended Northeastern University where he received a Master's degree and certification in elementary and secondary administration.

Mr. Calip came to Okmulgee High school from Waurika Public schools in 1981 as a classroom teacher; serving as an assistant football, basketball and baseball coach. While at Okmulgee, he was assistant principal and a successful basketball coach winning the Class 4A State championship in 1987 and State runner up in Class 3A in 1991. He later served as principal and coach at Boley schools and coached the basketball team to the Area finals. 

Mr. Calip presently serves as Assistant Principal at Okmulgee High School. He is a member of Uganda Martyrs Church and serves as Grand Knight for the Knights of Saint Peter Claver.