GWS and Bobby Hill’s management were working towards a contract extension as recently as late August.

Contracted for 2022, Hill told the Giants he wanted to be traded to a Victorian club late last week, as first reported by foxfooty.com.au.

On the weekend it was revealed his preference was Essendon, which has tabled a four-year deal for the small forward.

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Foxfooty.com.au understands Andrew McDougall of Corporate Sports and list manager Jason McCartney were having positive discussions regarding an extension into 2023 and beyond in the last few rounds of the season.

But GWS had one minor concern: Hill’s commitment in the off-season which had seen him return to training not as fit as they would have liked before Christmas last year.

With this in mind, the Giants informed McDougall they would prefer to wait until Hill returns from his summer holiday before committing to an extension.

If Hill was fit and ready to go, the club would have had no hesitation in locking the small forward in for at least another two seasons in addition to 2022 at some stage in the summer.

This was around the same time as Hill told the West Australian: “I am 100 percent keen to stay. This is the club that chose me on draft night so I don’t want to be that type of player. I want to show that love back to them.”

But for the duration of the finals series, communication went quiet. GWS didn‘t think anything of it, but Hill and his management were weighing up several options.

Then, around the same time as the Grand Final, the Bombers became aware of Hill’s desire to play for them. So when a trade request dropped, a deal was ready and waiting for Hill.

On October 7, foxfooty.com.au revealed Hill had emerged as a possible circuit breaker in negotiations around Rory Lobb.

And despite GWS wanting to keep Lobb’s pending arrival and Hill’s exit separate, the reality is the two deals are inextricably linked because both players are looked after by the same management company.

The Giants initially were frustrated to hear of Hill’s desire to leave and slightly confused as to why he had nominated Essendon on compassionate grounds when he’s from Perth and his cousin Bradley plays at St Kilda.

Hill called Leon Cameron to tell him the news and by Sunday Jason McCartney and Adrian Dodoro had touched base for preliminary discussions. The two list bosses clashed 11 months ago over Jye Caldwell’s exit and GWS are certain to want more than a third rounder for Hill this time around.

GWS is now resigned to losing Hill, but hasn’t ruled out trading him to another Melbourne-based club if Essendon doesn‘t pay up.

It is also keen to use Hawthorn as a third party to get a like-for-like player back in a trade, given they see themselves as in the premiership window.

That player is Chad Wingard, though it’s unclear whether the left-footer will entertain leaving the Hawks, where he is contracted until the end of 2023. The possibility of Wingard joining Toby Greene in the front half (from Round 6 onwards) excites GWS.

GWS would also ask Hawthorn to pay a portion of Lobb’s salary and send Pick 13 to Waverley Park.

Of course, there are several problems with these proposed arrangements. What’s in it for Fremantle aside from clearing cap space to lose Lobb? What if Wingard says no? What if GWS decides to send Hill to, say, North Melbourne instead of Essendon? Or St Kilda? Or any other Victorian team.

Driving much of these discussions behind the scenes are influential player managers Colin Young, Tom Petroro (TLA), and McDougall. Very rarely do their clients not get where they want this time of the year.

If Wingard digs his heels in, Petroro will not move him and GWS will need to investigate other options. Would Jack Gunston, who has a year to run on his contract, fit the bill? He‘s also managed by Petroro.

Unlike Jordan Dawson, Sydney and Adelaide, the parties only have three days to reach an agreement.

It took a while, but the trade period finally has some spice.