Just ahead of round eight, inaugural Sun and two-time Tiger premiership midfielder/forward Josh Caddy, 29, announced his immediate retirement after 12 injury-riddled seasons in which he played 174 games and kicked 164 goals. He was originally drafted by the Suns in 2010 ahead of their entry into the AFL and played 24 games in two seasons. He requested a trade back to Victoria for family reasons and moved to Geelong at the end of 2012. He went on to play 71 games for the Cats before being traded to Richmond at the end of 2016.
He had an excellent first season as a Tiger, playing 22 games, including the premiership. He followed up in 2018 with 46 goals, was nominated for All-Australian, and was in the top 10 for the Coleman Medal (AFL goal kicking) and Richmond's best and fairest. The next season in 2019 saw him start as a forward but he was later moved to a wing position. He was a member of Richmond's 2019 premiership team.