Former Aberdeen boss Derek McInnes has revealed for the first time the moral dilemma he faced over Scott McKenna's proposed switch to Aston Villa in 2018.
The Dons turned down a £5m-plus-offer for their prized asset as they held out for £7m from the Villans, with Celtic also keen at the time.
The Scotland international eventually left the Granite City for Nottingham Forest in 2020, for a fee of £3m with add-ons which could yet see Aberdeen secure £6m for their record sale.
McInnes has recalled the difficulty in balancing the need of the player, alongside doing what is best for the club itself.
His time for self-reflection comes after Hibs landed £3m for star man Martin Boyle from Al-Faisaly and allowing players the opportunity to make life-changing money.
McInnes admits he views transfers in a different light now but believes waiting for Forest rather than joining Villa might turn out to be the best choice for McKenna's career.
Speaking in his Mail on Sunday column, McInnes said: "I've had that experience of bids coming in where the club feels the fee is not enough, yet the player has the chance to go and earn five or six times their wage.
"And sometimes you're just put in an impossible position.
"That's what happened with Scott McKenna at Aberdeen when Aston Villa put a sizeable offer on the table in 2018.
"Clubs want to sell at optimum value, the best price. And in terms of guaranteed money, Villa was the right club and the right offer. The trouble is it came in at the worst possible time, in the last few hours of the transfer window.
"We had specifically asked Villa to do it earlier, that the deal wouldn't be done if they left it to the last day.
"So it was a deal that could have been done. And it would have worked out well.
"Aberdeen never did get the same money in the long run and it was difficult for Scott to overcome - for a while, things weren't perfect between player and club.
"Villa were a Championship club at the time and ended up getting promoted, which Scott had to watch from afar.
"Scott got down there eventually with his move to Nottingham Forest where he now has a great chance of getting to the playoffs.
"He established himself as a Scotland international in an Aberdeen shirt and he continues to be picked whenever Steve Clarke names a squad.
"Who is to say that would have been the case had he gone to Villa?
"But, with hindsight, I can really see it from the player's point of view."