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Demetriou probably timed his exit to allow the AFL to distance themselves from any fallout from this. (Don't know how this will work as McLaughlin seemed pretty involved with their strategy too).
Essendon seem to be rolling the dice big time by taking the legal path. They are saying the AFL/ASADA joint process was unlawful, apparently with regard to ASADA's charter where it demands privacy during the investigation, among other grounds.
If Essendon succeed the AFL, ASADA, AFP and the last Federal Government will cop flak. But the AFL will point at Demetriou. If they fail, all the individuals will likely get the maximum sanctions rather the 6-12 months being freely hinted at for full cooperation. Long way to go yet I suspect.