Cameron Mooney believes Essendon made a blunder by not trading wantaway forward Joe Daniher at the end of last season.
Daniher requested a trade to Sydney at the 2019, with the Swans reportedly offering the Bombers two first-round draft picks in return.
Essendon eventually opted to hold the 26-year-old to the final year of his contract.
Mooney said it was highly unlikely the club would be able to convince Daniher to re-sign just 12 months after handing in a trade request.
“I think Essendon made a big mistake not getting two first-round draft picks for him last year,” Mooney told Fox Footy.
“The hard thing is when a player is asked if he’d like to be traded if there’s ‘something there’, he’ll say ‘I’d prefer to stay but if there’s something there I’ll go’.
“But nothing happens and then he stays and he’s happy to stay. But when a player wants out, you can’t convince them in 12 months that they need to stay.
The premiership forward said he would be “staggered” if Daniher, who continues to work his way back from a long-term groin injury, played any footy in 2020.
“(Daniher) wanted out and I reckon he wants out again,” Mooney said.
“They made a mistake there I think.
“I’d be staggered if he plays (this year). I just don’t think he wants to play for them anymore.
“In my time in footy, I’ve never seen a player that wants out then turn around in 12 months’ time and say ‘actually I do love the place’. He wanted out, they should’ve let him go, they should’ve got what they wanted for him.
“Now I think it’ll be a lose-lose and Sydney should get him.”