Purely as a footballer I think he had 1 A grade year in 2018. 2017 and 2019 probably B grade. After that he has been quite non-existent despite hot VFL form and a slew of injuries in 2021 which probably tells you he wasn't in a good place mentally or the coaching panel probably thought he wasn't up to it at AFL level.
So in the pure playing sense I probably agree with claw. This is his 6th year on the list and only half of them have been worthwhile as a player.
Aside from that, as a bloke, a team mate, from a VFL development perspective, as a leader etc he has been excellent. One thing I really enjoyed about Caddy was his reputation as a bit of a campaigner. The 50m penalties he conceded were a pain but there's few things I hate more than seeing a Tiger get roughed up and no team mates go in for a scuffle. You could always bank on Caddy getting involved and looking after his mates and that is a big part of the culture that has made this dynasty happen.
Thanks Josh and GL.