Jye Caldwell was drafted by the GWS Giants with the 11th pick in the 2018 NAB AFL Draft. A combination of soft tissue injuries interrupted his draft year but the Giants recruiters had seen enough of the tough midfielder to see what he had to offer in the long term.
After impressing in his first two JLT games for Giants Caldwell was looking likely to debut in round 1 before sustaining a groin injury which GWS decided to treat with caution. He managed to make his debut in Round 21, playing a total of 11 games across two seasons.
At the end of the 2020 season, Caldwell was traded to Essendon.