Jewsbury attended Kickapoo High School in Springfield, Missouri, where he scored a state record 59 goals in his senior season and 124 goals in his four-year high school career. He was named First-team All-Midwest Region, All-State, All-District, All-Ozark Conference and conference Player of the Year as a senior, and was a three-time All-District and All-State selection, before having his #21 jersey retired.
Jewsbury played five years of college soccer at, finishing his career tied for tenth on the school"s all-time scoring list with 101 points. Jewsbury was twice named first team All-Conference United States of America, winning the Conference Player of the Year award as a sophomore.
During his college years, he also played with Kansas City Brass in the USL Premier Development League.