battling with what?You're battling here mate
You said there was no opportunity for Essendon to double dip. I don't know if you noticed but last night the bid for Kako came after where Essendon's selection was. So that is exactly what they would have been able to do.
Even if St Kilda had bid, which they wouldn't have, you had 6 weeks to plan for live trades so that you got something for pick 9. North just gave their f1 for 27. You would have had 15 clubs queueing up making you offers for pick 9.
Instead your rookie list manager panicked.