In an era when the Demons have misfired at the draft table more than any other club, Frawley is one of the biggest post-2006 hits.
'Unrestricted' Frawley free to leave Demons at end of year
The 2010 All Australian is also just 25 and only entering his eighth AFL season, the minimum free agency service period.
Surely, the Demons would have ensured that if they couldn't re-sign Frawley before his name appeared on the AFL's official list of free agents, then he would at least be among the restricted free agents.
That way they could ward off any rival suitors simply by matching whatever offers they threw at their man.
But when the AFL released its free agency list on Tuesday Frawley was among the unrestricted free agents. Put simply, this means if he wants to leave Melbourne at the end of the season, there's nothing the Demons can do to stop him.
How could the Dees let things get to this? The simple answer is by heavily front-ending the four-year contract Frawley signed in May 2010.
If you averaged the money Frawley earned across the term of that contract, he would be among the Demons' top five highest-paid players - well within the top 25 per cent pay bracket required to be a restricted free agent.
But by paying him a large whack of that money in his first and second seasons, the Dees ensured he fell out of that key pay bracket this year.
Which means the Dees could lose Frawley and be left with just another draft pick as compensation.
It seems like a massive blunder, but there are significant mitigating circumstances.
It's easy to forget that when Melbourne negotiated Frawley's contract in 2010, the Dees' list at the time was widely seen to be bursting at the seams with future stars.
So it seemed prudent to create salary cap room in future seasons to look after the raft of kids plucked at the pointy end of the draft. Front-ending Frawley's contract helped them do that.
Free agency was also just an idea back then. Yes, the AFL Players' Association had put it firmly on the agenda, but it would not be rubber-stamped until 2011, with most of the finer details then thrashed out ahead of the 2012 season.
How could the Dees have known that paying Frawley handsomely up front would end up increasing their risk of losing him at the end of his contract?
Obviously, nearly four years later, Melbourne fully appreciated that risk so it tried to take Frawley off the market by signing him to a new contract ahead of the 2014 season.
It is well documented that Frawley resisted the Demons' overtures, putting off contract talks in February.
Understandably, he wants to see some light at the end of the Demons' on-field tunnel after the club's extended run of misery. Understandably, he wants to see if things will change under new coach Paul Roos.
In that sense, it probably does not ultimately matter whether Frawley is a restricted or an unrestricted free agent.
In free agency's previous two years, no club has matched an offer put to one of their unrestricted free agents, not even with stars like Lance Franklin, Dale Thomas and Brendon Goddard.
It seems if you get to the 'rival offer' stage, the player has already made up his mind to leave and his club knows better than to try and stop him.
Melbourne's challenge is to re-sign Frawley well before then.
It's best hope of doing so is to give him hope; hope that the years he has spent in the football wilderness will be rewarded with better times ahead.
If the Demons can give him that, Frawley is unlikely to go anywhere.
Below: Star defender James Frawley and No.1 draft pick Jack Watts back in 2012. Picture: AFL Media
Twitter: @AFL_Nick.