The issue is (as has been recently) the difference in how Hawthorn have weighted trade value (be it draft pick number or player) vs the reputation and credibility gained with players (their own and other teams) that they will put the player first.
GC (and AFL) used and abused that with JOM. Hawthorn met GC initial trade demands, then GC moved the goalposts. HFC went to AFL, and AFL backed the GC - Hawthorn, having made a commitment to JOM went above and beyond to honour the deal. Eventually the AFL forced the GC to take the trade as it was weighted so far in their favour. (Saints just the lucky club to win the bonus picks so GC could save face despite the final offer being substantially less 'value' than the first offer made.
If JOM comes back "as good as he was" pre-knees then it's a fair price, but that would be extremely doubtful IMO. A "Burgoyne/Cyril-esque" player (MVP quality, but only available in bursts due to injury/fitness) a small loss, with a large over-payment the most likely outcome.
Similarly, HFC accepted substantial "unders" in return for Mitchell, Hodge and Lewis - all of whom allowed (encouraged) to negotiate their own best deal as a thank you for years of underpayment. The club then took what it was offered, no fuss.
Since that time, HFC has been far more guarded in it's stated intentions and media release.
This then contributed to losing Burton when Port cynically played the media and Ryan's family with "mis-truths" which HFC did nothing to deny publically, and by the time they contacted Ryan (early morning in US), he'd already seen Australian media, spoken with family and the storyline was set. HFC then followed their "player welfare first" mantra, essentially giving him to Port as per his wishes in the Wingard trade.
There have been quite a few 'unlucky' misses in the last 12 months, which no doubt colours the general public's view.
Lynch - HFC was the only club that could meet all of his stated demands (public and in negotiation) - salary, no senior players cut/traded, easy move without GC matching. HFC was very confident, especially as GC could not match (nor could any other club) the negotiated deal. He then signed for RFC, compromising on his demands to get a longer contract term (but less money in yr.1+2 - allowing GC to match and trade). The AFL had to 'encourage' GC to not match the offer and RFC helped grease the wheels a little. HFC had spent close to 2 years on that bid - according to a few sources Clarko having committed to Lynch ala JOM "at the expense of everything else".
Gaff - HFC was an option before the incident, NM was always the $$ offer, HFC offered the community/support/success but after the incident Gaff's mental state was such that Clarkson (no doubt amongst other confidants) encouraged him to stay at the Eagles.
Shiel - HFC was a frontrunner, along with EFC and Carlton. Shiel and GWS were happy to go whoever offered up most, Shiel not wanting to be the 'main man', wanting a good midfield around him. EFC offered 2x1st, GWS informed other clubs of offer, HFC told GWS they wouldn't offer that. GWS told Shiel's management of HFC withdrawal (Carlton/EFC left), Shiel (classy move) rang each coach individually to advise he was going to EFC and his manager started finalising contract with EFC. EFC then backed out of 2x1st deal, GWS re-opened negotiations with HFC. Scully deal enabled GWS to keep Shiel (who again showing his professionalism was happy to stay), with EFC eventually forced to hand over the 2x1st picks.
It's doubtful Hawthorn could have landed all of Lynch, Gaff, Shiel - and even if they did it would certainly have ruled out Wingard and Scully (probably keeping Burton). It is, however indicative of the value that a sizeable 'warchest', and being an attractive destination (recent success, historical success, financial stability, large membership and of course Clarkson and his coaching legacy) has in catching the eye of prospective players.
Hawthorn rate their recruitment and development - seeing little difference in value of picks 6-20, 21-50, etc. Due to success they haven't had regular access to top-10 picks the regular cellar-dwellars like Carlton, EFC and Melbourne have. They believe they have the best medical/rehab/fitness team, and have used this to their advantage when dealing with less professional teams - getting players for unders. They regularly 'make it simple' by paying overs/accepting unders in trades, working on a community culture amongst the players (which they no doubt utilise when negotiating salaries, hence the continual growth of the warchest in cap space). Finally, they have Clarkson - who has half the league as former proteges, and whose counsel is sought by many players (young and established) for his reputation as being able to provide compassion and understanding, guidance and direction without "wearing a HFC cap".
It remains to be seen if it can be continued into the future and generate anything more than finals and top-4, but when dealt with the cards/picks that Hawthorn have been given over the last decade - IMO they have done remarkably well.