Calkins begins his first year as a graduate assistant at the University of the Cumberlands in 2019. Calkins brings NCAA Division I experience to the Patriots in the wrestling room after his collegiate career at Oregon State. He served as a three-year starter for the Beavers under coach Jim Zaleski. Calkins accumulating 44 wins against Division I opponents during his collegiate career, including a sixth place finish at the Midlands Tournament, third at the Road Runner Open and first at the Mike Clock Open.
Before his stint with Oregon State, Calkins was a two-time state qualifier for Montini High School, taking the Illinois state championship title in the 126 lbs. weight class his senior season. He was also twice a Fargo All-American after placing fifth and second at the national meet.