Grimes is a Wichita native who graduated from North High School in 2008 where he won a city league title his junior and senior year. He additionally made first team all city all four years, first team all state for two years, and first team all metro for two years. He then went on the play baseball at Wichita State University and started for three years at short stop. Grimes was drafted in the 5th round by the Minnesota Twins in 2011, where he played 5 seasons. During his time within the Twins organization, he played for the Cedar Rapids Kernels, Beloit Snappers, & Ft Myers Miracle.