Pykie
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The question is though, besides Gills stick saying that would be a bad look and we would prefer if you didnt... Is there anything in the rules that would prevent it from happening.
Rules, probably not, I'm sure there's a few hundred pages in the AFL's standard playing contract that works against your theory. I can't think of a single instance where a player has opted out of multiple years in their contract for anything other than mental illness or injury. It would of already happened if it was possible I imagine.
He also wouldn't be a free agent, I imagine he would be a delisted free agent.