Levy isn't an idiot. He's a very intelligent businessman who has done a lot of fantastic work off the pitch for this club which has changed our future for the better, undeniably. I may criticize him plenty, but I far from want rid of him and absolutely appreciate that he pulled our club away from a very dangerous position. I do however believe that's he's a man who values profit over all, thus we will potentially have issues with taking the next step in order to properly compete for trophies. Is Levy the kind of man who will take risks by investing in the squad in order to take the next step and win a trophy/compete for a title? Or is he perfectly content with Pochettino's management gaining us top four season after season and failing at the semi-final stage? I think it's the latter, and that the situation suits Levy. For him, the financial risk it would take to really push the squad up a level probably isn't worth the risk. Levy isn't a charitable man, he's not bringing in a new stadium out of the goodness of his heart, he's thinking about future revenue.
When it comes to matters on the pitch, Levy can be out of his element. I think his tactics regarding transfers have often been to the detriment of the squad (last minute rushed signings, punts etc) in which he's focused more on trying to be a 'tough negotiator' than what the manager actually requires. He's done this a number of times and each time it gets criticized and usually does backfire, yet he continues to do it. We also went through some pretty poor managers (AVB was a hideous appointment who was bound to fail and made no sense) so in terms of the footballing side of things, he has made plenty of errors. Pochettino came out and said we needed to 'be brave' and focus on being properly prepared for pre-season with some fresh arrivals, and he got the exact opposite, to the point where he now seems unsure of whether he'll get any reinforcements. Maybe this pre-season game will be a message to Levy that it is needed.
There is money to spend, we're not destitute. Of course the new stadium means that the purse strings have to be tightened, but we have very healthy revenue already and have for a long while been in austerity mode with a number of seasons of low spending (net wise lower than the likes of Palace) and also spend far less on wages than other top clubs. We obviously can't afford to splurge hundreds of millions, but it was expected that this window would be a statement that we weren't going to 'do an Arsenal' and allow the squad to rot in favour of stadium repayment, that we did want to compete and back our manager .. but we were wrong. Basically, not an idiot like a Mike Ashley, but not a footballing man and he's expecting Pochettino to work with far too little. We badly need to act quickly with very little time to go, or we're going to be left in horrible shape for the first few games of the season.