Courtenay Dempsey

Recruited from Morningside in Queensland with pick 19 in the 2005 National Draft, Courtenay Dempsey was a naturally gifted player whose career at Essendon was defined by flashes of brilliance interspersed with significant injury setbacks. Operating primarily as a rebounding defender, Dempsey used his pace and agility to break lines off half-back, offering a level of attacking flair and creativity that made him a dangerous weapon in transition. Despite his obvious talent, he struggled to remain on the park consistently, battling recurring soft tissue issues and a serious knee injury in 2011 that required reconstruction.

Dempsey's time at the elite level came to a difficult conclusion due to the fallout of the Essendon supplements saga. He was one of the 34 players suspended for the entirety of the 2016 season, and although he served the ban, he was delisted by the Bombers later that year without adding to his 133 games. Ultimately, he is remembered as a dash-and-dare defender who provided spark for the Dons but was rarely afforded the continuity needed to reach his absolute ceiling.