Jack Charleston competed at Cooperstown Dreams Park during Week 6 in 2004 with the Diamond Bandits (FL) and Week 5 in 2005 with the Santa Fe Sluggers (FL). He was crowned Week 5 Golden Arm champion during the Skills Competitions events in 2005.

Jack, a right-handed pitcher, went on to graduate from F.W. Buchholz High School (Gainesville, FL) where he played baseball all four years and one year of football. As a senior, Jack went 3-0 with a 3.28 ERA and a .357 batting average. He was a two-time honorable mention All-Area selection. After high school, Jack attended and played baseball at Flagler College (St. Augustine, FL). He transferred to Santa Fe College (Gainesville, FL) before settling and playing at Faulkner University (Montgomery, AL). While at Faulkner University in 2015, Jack posted a 10-1 record with a 1.70 ERA, 83 strikeouts and four saves in 18 games. He was named the SSAC Baseball Pitcher of the Week during the last week of April, 2015.

Jack has made the leap to professional baseball. He was drafted by the Chicago White Sox in the 2015 Major League Amateur Draft.