Carlito
Player Valuation: £40m
After the initial splurge didn't work out, there should have been a move towards overhauling the club's off-field performance with a view to becoming self-sufficient (commercial deals, executive appointments, recruitment department, etc).Unfortunately I think the problems are multifaceted. I agree with the general thought that Kenwright would be gone by now but Moshiri has been suckered in with the Bill does everything right - clearly he got lucky with Moyes. Without the money to spend more often than not we ended up with 'Everton' type players who if they wanted to win trophies had to play well enough to get in the shop window. Opposed to everyone starts on big money and will never go on to bigger things or had already stepped down.
Moshiri has interfered thinking it's a pick n mix, although to be fair how many players we don't know...Iwobi for sure.
The hegemony of the big clubs already upset having had City and Spurs break into the CL group's cash has pretty much scuppered us right from the off, 1) there were already 6 big clubs with more money and better players to cockblock us from trophies and finishing in a position that allows us to get Europe and see that progress that makes everyone believe we are heading in the right direction and 2) I wouldn't put it past them that they've already bribed whoever they need to to keep us down.
It was always going to be struggle. Our only foothold was ruined when we decided to buy 4 number 10's than get 1/2 world class players in our weakest positions. And of course Ancelotti doing a bunk...the cockwomble.
Instead, what we have is a situation where we've kicked the can down the road from where we were heading under Kenwright and Martinez in 2016, relying on cash injections that, as you say, the protectionist rules have now outlawed.