Alfredo Morelos is already on his way out of Rangers for free- and there's no way for the club to force contracts on stars to avoid future situations.
The Premiership side were in a similar boat last season when Connor Goldson took his contract talks down to the wire before agreeing new terms. But similar has not transpired this season, with Morelos running down his contract after failing to come to terms with Rangers during a disappointing term.
Ryan Kent is in a similar boat and Turkish reports have claimed he is close to agreeing a free transfer to Fenerbahce. Incoming CEO James Bisgrove is putting major faith in a player trading model which has brought in big bucks recently through three big sales in the last 18 months, but contract situations can sometimes fall out of their control. Asked if it was something the club had to learn from, Bisgrove explained: "Potentially. It has been spoke about before by the manager and Ross (Wilson, former sporting director) when he was here.
"We can not force or insist a player to sign a contract. It is there prerogative to take a decision but what is important to us is getting the player trading model right, which means our recruitment decision need to be spot on and backed up by great scouting, analytics and they need to be the player the manager wants.
"We also need to build value in the squad. I think you saw us execute that plan with Calvin Bassey, Joe Aribo and Nathan Patterson. It's never a perfect art but the player trading model is one we believe in and we have shown in can work at Rangers."