He was recruited by the Greater Western Sydney Giants with pick 11 in the 2018 national draft.

[2] Caldwell was recruited by the Greater Western Sydney Giants with pick 11 in the 2018 national draft.

[3] He made his senior debut in the 56-point loss against Hawthorn, in round 21 of the 2019 AFL season at Manuka Oval.

[8] Caldwell returned for Essendon's elimination final defeat against the Western Bulldogs at York Park in Launceston.

[9] In 2024, Caldwell had a "breakout season", getting more midfield time and thus becoming one of Essendon's best players and most important midfielders,[10] including winning Essendon's player of the month award in June of that season.