Collingwood are in for one of their most challenging AFL off-seasons as the Magpies contend with a bulging salary cap and a number of out-of-contract stars.
Compounding the misery of an embarrassing finals exit to Geelong last Saturday night, Collingwood hierarchy have the giant task of keeping some of their best talent at the club.
Electric forward Jordan De Goey, All-Australian defender Darcy Moore, leading goalkicker Brody Mihocek and emerging star Josh Daicos are all yet to re-sign with with the Pies.
Moore and Daicos, both sons of Collingwood royalty, won't be going anywhere, but De Goey and Mihocek are eyeing upgraded deals.
De Goey is without a professional manager and has instead been assisted in contract negotiations by his father.
Speculation has linked the 24-year-old to two of the club's fiercest rivals, Essendon and Carlton.
Collingwood coach Nathan Buckley has conceded money will be the biggest factor in De Goey's decision.
"Elements of people on his side would like to see him remunerated as well as he possibly could and we want him to be rewarded appropriately as well," he said after the 68-point semi-final thrashing to the Cats.
Late bloomer Mihocek, who only debuted in the AFL aged 25, also wants to capitalise on his career as this may be his one and only opportunity to secure a lucrative, long-term contract.
The 27-year-old has been the Magpies' leading goalkicker during the past two seasons and is certain to attract interest from rivals clubs should he want out.
The club had to pay up to keep dual All-Australian ruckman Brodie Grundy, who was toying with the idea of returning home to South Australia.
After penning a seven-year, multi-million dollar deal in January, Grundy was well below his All-Australian best this season.
Premiership midfielder Dayne Beams was expected to be the missing piece to another Collingwood flag after he returned to the club following the Magpies' 2018 grand final loss.
But Beams, who still has two years to go on his contract, hasn't played since June 2019 after stepping away from football to work on his mental health.
Adding to Collingwood's complications is Adam Treloar's partner Kim Ravaillion is expected to sign with the Queensland Firebirds for next year's Super Netball season.
The star midfielder wants to stay with the Magpies but Treloar and Ravaillion have a young child together and the couple would need to separate their time between Brisbane and Melbourne.