He previously played for the Marshall Thundering Herd Pennington grew up in Versailles, Kentucky and attended Sayre School where he lettered in football and basketball.

During his high school career, he led the Spartans with a 16-4 all-time record and threw for over 4,000 yards and scored 56 total touchdowns with a 70% completion percentage.

[1] He was a three-star rated recruit and committed to play college football at Marshall University over offers from Akron, Ball State, Eastern Kentucky and UT Martin.

[4] He became the starting quarterback during a game against Coastal Carolina after an injury from Cam Fancher, where Pennington completed 12 out of 23 passing attempts for 77 yards and two interceptions.

[5] During the 2023 Frisco Bowl, he completed 15 out 33 passing attempts for 258 yards as the starting quarterback.