List manager Danog is on the case. This is a tl;dr that I've done on the train in to work.
I'll piggy back off the trade suggested by
no.11
Richmond Pick 6 & 27 (Points = 2454)
to
Sydney Pick 14 & 17 (Points = 2186) + Nankervis
Leaves us with 14, 17, 46, 64, 82
Gold Coast currently have 4, 8, 22, 24, 26, 30, 44. There's a new rule in place that you can only use draft picks for father/son & academy bidding relative to the amount of vacant spots on your list. For example, if Gold Coast only has 6 vacant spots on their list, they can't just use 4, 8, 22, 24, 26, 30 in the draft and then bank 44 to use as points. Pick 44 is essentially useless. So, if they're going to be getting MORE picks for Prestia / O'Meara, then becomes even more of a problem. I highly doubt that they'll use 44, or any picks after it (62, 80, etc).
So what does this mean for Richmond? It means that we can upgrade our later picks.
I would trade 14 and 82 to Gold Coast for Prestia, 44, and 62. If Gold Coast got snippy about it, then we could throw in a 2017 4th rounder too (in the 60s).
If they still chuck up a fuss, then we go to the AFL for mediation. Prestia is out of contract, does not want to play for Gold Coast, and has specifically nominated Richmond as his club of choice. Because of our (proposed) trade with Sydney, 14 is now our earliest available pick. If they say that's still not enough, state the Hawthorn traded pick 14 for Tom Mitchell, a proven finals performer. Who are Gold Coast to say that Prestia, who hasn't played close to a full season in 2 years, has had injury concerns, and is yet to prove himself in finals, is worth more than Tom Mitchell? In fact, it makes him worth slightly less, hence the pick upgrades that don't impact on Gold Coast at all.
Assuming this goes through, we now have 17, 44, 46, 62, 64.
We can then trade Deledio and 44 to Geelong for Caddy and 56.
End result is that:
Richmond lose 6, 27, 44, 2017 4th rounder, and 82.
Richmond then have 17, 46, 56, 62, 64, Prestia, Caddy, and Nankervis.
If we don't have enough list spots to use all of those later picks, then trade the later ones to get back into the 3rd or 4th rounder in 2017. Hawthorn would probably bite, given that they've traded away a ton of picks.
Simples.