Swaggerty attended Denham Springs High School in Denham Springs, Louisiana, and played on their baseball team. As a senior, he batted.451 and was named to the Louisiana Sports Writers Association's Class 5A All State team. He was not drafted in the 2015 Major League Baseball draft and enrolled at the University of South Alabama where he played college baseball. As a freshman in 2016 at South Alabama, Swaggerty appeared in 59 games, compiling a.303 batting average with four home runs, 27 RBIs, 12 doubles and 20 stolen bases. In 2017, as a sophomore, he appeared in and started 58 games, slashing.356/.484/.571 with 11 home runs, 60 RBIs, and 19 stolen bases. After the season, was named to the All-Sun Belt First Team. That summer, Swaggerty played for the USA Baseball Collegiate National Team where he batted.328/.449/.406 in 19 games, and also briefly played collegiate summer baseball with the Brewster Whitecaps of the Cape Cod Baseball League. He was named a first-team preseason All-American by Baseball America, D1Baseball.com, and Perfect Game prior to his junior season along with being named the 2018 Sun Belt Preseason Player of the Year. He finished his junior season batting.296 with 13 home runs, 38 RBIs, and a.455 on-base percentage over 57 games. He was named to the All-Sun Belt First Team for the second year in a row. The Pittsburgh Pirates selected Swaggerty with the tenth overall selection of the 2018 Major League Baseball draft. He signed for $4.4 million and was assigned to the West Virginia Black Bears with whom he was named a New York-Penn League All-Star. After hitting.288 with four home runs and 15 RBIs in 36 games for the Black Bears, he was promoted to the West Virginia Power in August. He finished the season with the Power, batting.129 with one home run and five RBIs in 16 games. Swaggerty spent 2019 with the Bradenton Marauders, earning Florida State League All-Star honors. Over 121 games, he slashed.265/.347/.381 with nine home runs, forty RBIs, and 23 stolen bases.
