Robbie Gray is Port Adelaide’s second best player in the AFL era behind Warren Tredrea.
Upon retirement, Gray will be an automatic inclusion into the Australian Football Hall of Fame. He is a three-time John Cahill Medal winner, four-time All-Australian and five-time Showdown medallist.
At 32, Gray becomes an unrestricted free agent at the end of this season.
After attracting some interest from rival clubs in the 2019 AFL trade period, Gray chose to remain loyal and to see out his contract at the Power.
Gray’s contract situation poses a massive conundrum for the Port Adelaide list management team. He will start the 2021 season at 33 years of age and has somewhat of a fragile body that constantly needs to be managed throughout the year.
With those factors at hand it seems Port Adelaide would be comfortable offering him a 12-month contract extension with performance clauses included, that if met, would extend the deal to two years.
Would Gray accept such an offer or would he look at a longer-term deal from a Victorian club who is in the premiership window?
Melbourne dished out a three-year deal for Jordan Lewis who was in a similar stage to Gray when he departed Hawthorn. Gray is a much better and accomplished player than Lewis.
Collingwood gave the same tenure for former North Melbourne midfielder Daniel Wells even though Wells' body had continually let him down.
Adding to the temptation for clubs to lure Gray is his free agency status meaning any club can sign him without giving up a thing.
Gray and his wife Annabel hail from Victoria and both have significant family ties back home.
Gray hasn’t played in a winning final since 2014 and the one missing link from his illustrious career is a premiership. It would be tempting to join a contender such as Collingwood or Richmond, the latter now having more salary cap room after the departure of Alex Rance.
Hawthorn coach Alastair Clarkson has been a long-term admirer of Gray’s and a move to the Hawks would also make complete sense.
Complicating the negotiation is Gray’s friendship with Port list boss Jason Cripps.
Can Cripps separate his personal relationship with Gray and put the interests of the club first?
Particularly after Cripps has made significant mistakes by committing long-term to players such as Paddy Ryder, Charlie Dixon, Jack Watts, Steven Motlop and Tom Rockliff, all of whom have underdelivered.
It would be a bitter blow for Port fans to see Robbie Gray finish his career in anything but black, silver and teal.
Negotiations are all about power. Gray and his manager Tom Petroro hold all of it.
Port Adelaide players out of contract at the end of 2020
Unrestricted free agents
Robbie Gray - 32 in March
Travis Boak - 32 in August
Justin Westhoff - 34 in October
Restricted free agent
Brad Ebert - 30 in April
Free agents
Charlie Dixon - 30 in September
Jack Watts - 29 in March
Others including: Sam Powell-Pepper, Cam Sutcliffe, Willem Drew, Trent McKenzie, Wylie Buzza, Jarrod Lienert and Joe Atley