It goes back to when we believed that players contracts would get shorter and that wages would be the paramount factor - to support that theory we started paying higher wages and allowing contracts to run down ... this wasn't an accident it was bad management.
Why five years later is that still a problem? Well there are two main reasons, firstly we have 'older' players who we either allow to leave for free or pay massive salaries for their final contract - Ozil, Auba, Willian, Luiz all on big money all who have left or will leave for almost no transfer value, secondly we have very average players Bellerin, Kola, Xhaka, Soares on 100k a week or more, no other club will take them on and pay a decent transfer fee - those high salaries also mean other players Partey, Pepe, Tierney, Martinelli will only sign for similar huge wages ....
This creates a never ending cycle - older players on big salaries leaving for free at end of contract (256m asset loss in the last five years) - overpaid average players either on gardening leave whilst their contract runs down or we pay other clubs to loan them - new players signed on very high salaries some of whom become overpaid average players either on gardening leave whilst their contract runs down or we pay other clubs to loan them.
It also means youngsters have almost no chance of getting in the squad and look to move away.
It's a cluster-feck that goes back years and sadly is very much still with us - when we have a wages bill similar to Chelsea and Liverpool yet a squad that's not even close (and don't even mention Spurs !!!!!!) something is badly wrong.
Unfortunately the solution is drastic, get rid of Auba, Laca, Willian, Luiz and lose another 250m in asset value, get rid of Bellerin, Kola, Pepe, Xhaka and take whatever we can get for them .... bring in 8 or 9 players under 27 on 50k maximum and make them earn bonuses and pay-rises ... the trouble is that will be a huge risk with an inexperienced manager at the helm, and our recruiting team so far hasn't been up to the task.
But if we don't change we will see not only City, Utd, Liverpool and Chelsea move out of reach but also Spurs, Everton and possible others. You can't operate a club on a failed philosophy even one as big as ours.