Plumlee grew up in Hattiesburg, Mississippi and attended Oak Grove High School, where he played baseball and football. He became the Warriors starting quarterback as a sophomore. As a junior, he passed for 1,759 yards, 14 touchdowns and nine interceptions and rushed for 599 yards and eight touchdowns in nine games and was named to the "Dandy Dozen" by The Clarion-Ledger. In baseball, he batted .442 with 35 RBIs and 38 runs scored in 27 games. Rated a four star recruit, Plumlee initially committed to play college football at Georgia during the summer going into his senior year over offers from Auburn, Alabama, Notre Dame, North Carolina, Nebraska, Southern Miss, Tulane, Troy, South Alabama and Mississippi State. As a senior, Plumlee complete 187-of-291 passes (64.3 percent) for 2,834 yards with 33 touchdown passes and three interceptions while also rushing for 1,444 yards and 19 touchdowns on 162 carries (8.9 yards per carry) and led the team to a Southern State championship before losing to Horn Lake High School. He finished his high school career with 5,430 passing yards, 2,314 rushing yards and 82 total touchdowns in three seasons. After the season, Plumlee de-committed from Georgia shortly before National Signing Day in order to accept as scholarship to play both football and baseball at Ole Miss. Plumlee batted .411 with 39 hits, 45 runs socred, seven doubles, five triples, two home runs and 24 RBI in 29 games and was named 2019 5A/6A All-State in his final baseball season at Oak Grove.

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