Caldwell opened the 2025 season with 36 disposals against Hawthorn and later had 16 touches in a single quarter in Brisbane, the most by an Essendon player in a term. He was limited to 11 games that year. The 183cm midfielder won the Adam Ramanauskas Most Courageous Player award in 2024 and has since joined the Bombers' leadership group. He has played 106 AFL games and kicked 37 goals.