I've been around enough executives and decision-makers to know that they often have an inflated opinion of their own preparedness for eventualities. Hell, part of my job is foresight-centric - understanding possible futures and then briefing executives on their preparedness (diplomatically, of course).
In Levy's case, no doubt he knows Mourinho, and has wanted him in for a while. I also suspect he's a) bought into Mourinho's charm offensive (which has happened to smart men in football before), and b) believes he can wrangle Mourinho into submission, should he start his typical second season act of demanding signings to make a push for the title.
I happen to think he's wrong about that second point, because Mourinho's media presence is much, much larger than Levy's, and sympathy for Levy's penny-pinching narrative will run out quickly given how Poch was sacked after not being backed. Mourinho has the press eating out of his hand - Levy does not. And Mourinho is unscrupulous enough to use that to full effect, unlike Poch.
Hence, I don't think Levy quite understands who he's dealing with. If he did, he wouldn't come out with this penny-pinching bargain-bin stuff he's been doing for twenty years.
Hopefully Levy spends money, gets players in early and backs his man this time. If not, it won't end as quietly as Poch's time here did - we lost a good man and appointed a global prima-donna in his place, and that will have consequences for how Levy's delay, delay routine will go down.
The issue here is youve assumed a position on Levy, only to then argue against it. All very conveniently wrapped up in the narrative youve constructed.
The problem I have reading it is this.
Has Levy ever struck you (or anyone) as not being prepared? Or as being so egotistical he thinks he can control the like of Mourinho?
I have to say, for me, the answer to both is a flat NO. Which leaves the rest of your post unravelling as I read it.
Levy managed Redknapp just fine, another media savvy (with media clout) manager who loves to buy players time and again.
Levy has shown willingness to be opportunistic, but also planning and execution time and again.
I cant help feeling with the summer that wasnt, it really did come down to exactly what he said - an inability to make room for players, as well as the market not offering much in the first place.
Allied to Poch being keen on a policy of only signing players to really strengthen - it seems to me an unfortunate confluence of circumstance is the most likely "truth" than any sort of conspiracy or caricature of Levy being Scrooge.
Mourinho? Youd have to be deaf, blind and having spent the last 15 years living on the moon to not know what he is and how he is likely to behave.
We've all seen the charm elsewhere, we've all seen how it goes. Personally I credit Levy to know EXACTLY whats going on there and to not be so full of himself to think he can change him.
Again, occams razor - theyve had conversations already about what is/isnt going to be available. Simple as that.
If Mourinho tries to move the goal posts later on, then its something to deal with at the time. But Id be confident right now in Levy holding up his end of whatever bargain they have made.