OVER lamb shanks and a bottle of red at Benny's Bar in Fremantle, Melbourne officially made its move to lock in their superstar Kysaiah Pickett on an historic deal.

It was the crucial catch-up in one of the biggest contract turnarounds in modern football.

Demons list boss Tim Lamb travelled to Perth a month ago and arranged a dinner with Anthony Van Der Wielen, who had become Pickett's new manager in April. They met at the Fremantle eatery, where Lamb presented the new nine-year deal to keep Kozzy a Demon.

On Thursday, following AFL.com.au revealing the mammoth offer and Pickett's intentions to sign it this week, the Demons confirmed their gun 24-year-old had locked in until the end of 2034, when he will be 33. The deal makes him the longest signed player in the AFL, surpassing Fremantle's Hayden Young (2033).

That Lamb and Van Der Wielen met in Dockers heartland is part of the twist; only months earlier, Pickett had told the Demons and Dockers during last year's trade period that he was keen to head back to Western Australia to join Fremantle. Those feelings had remained even early in this season.

Van Der Wielen, who also manages Shai Bolton and Tim Kelly among other AFL players, was engaged as Pickett's manager in April around Gather Round. It was anticipated that Pickett signing with a West Australian-based manager would only strengthen his desire to join a West Australian club at the end of this season, despite having two more years to run on his existing deal with Melbourne.

When the player and his new agent first discussed his future together, Pickett indicated he was still keen to seek a trade. But the option of staying in Melbourne was kept on the table by Van Der Wielen, who put forward cases where players had left Victoria and moved to WA where it worked, and those where it didn't, including former client Jeff Farmer.

Melbourne wanted to be proactive to keep Pickett, knowing he had been restless and homesick at different stages of his glittering young career. They also knew he was about to enter a new phase of his football career with more midfield time as an up-the-ground weapon.

As the Demons pieced together a long-term option to keep Pickett well into the future, it became clear to the 2021 flag-winner and his agent that arranging a trade whilst in contract was going to be super difficult. The club's public stance, headlined by Simon Goodwin's "he's not going anywhere" comments, was backed up privately as well. They were firm a deal wasn't going to be entertained.

Different versions of long-term offers were discussed. They included a Zak Butters-type of offer, which would have seen Pickett offered two more years - to get him to unrestricted free agency - and then the option of adding another five years beyond that.

An exit clause, allowing Pickett to leave if he wanted after a certain amount of seasons, was also discussed but not included in the final iteration. Unlike Mac Andrew's huge deal at Gold Coast, which can go through to 2034 if he reaches a games mark, there is no trigger.

The morning after the lamb shanks dinner, Van Der Wielen called Pickett to relay the details of the offer. It would be footy's most lucrative deal, worth around $12 million, with his next two seasons' pay restructured as well. It was essentially a new nine-year agreement and it was Melbourne's way of expressing its keenness to get it done.

More conversations in the following weeks developed, including another catch-up in Melbourne with football boss Alan Richardson, with Pickett settling on wanting to stay at the Demons about a fortnight ago. That it has combined with a career-best run of form that has him in All-Australian contention didn't hurt the Dees' chances.

As Inside Trading reported last week, Van Der Wielen travelled to Melbourne last week for a couple of days to sit down with Pickett and his partner Ardu to talk through the extension before absolutely proceeding. The Dockers were kept in the loop that it was heading the way of a major recommitment at Melbourne.

There is a reality that given Pickett's change of mind in recent seasons – he has also flirted with a move to Port Adelaide before – that at different stages in the long-term deal, he will be homesick again. That is a risk Melbourne will be willing to carry to also have control of any trade requests down the track.

But the club is extra supportive of him and his family, he is tight with teammates and his coach, and is looking at also moving down the Mornington Peninsula - where a number of his teammates already reside - to get further out of the hustle and bustle of the city.

Melbourne has Christian Petracca and Clayton Oliver on deals worth $1.2 million plus, but otherwise has a relatively flat group of earners given the prominence of key veterans in their group and the emergence of younger players who are still either on their first or second contracts.

By the time the current Collective Bargaining Agreement ends in 2027, most clubs are expected to have at least three million-dollar players on their list. Pickett belongs firmly in that group.

Longest contracts in the AFL

Signed until 2032
Noah Balta (Rich)
Luke Davies-Uniacke (NM)
Connor Idun (GWS)
Max King (StK)
Aaron Naughton (WB)
Connor Rozee (PA)
Sam Taylor (GWS)

Signed until 2033
Hayden Young (Frem)

Signed until 2034
Kysaiah Pickett (Melb)