Newcastle are prepared to go to the wire in pursuit of their remaining transfer targets, in a bid to knock millions of pounds off transfer fees, but playing a game that could backfire.
It only takes interest from other clubs to create a situation where PSV ... and whoever ... are sick of Ashley trying to get blood out of a stone.
Then we could end up with NOBODY! Just as we did in January when Carroll was shipped out and it was too late to bring in a replacement.
With the summer window entering its last few days, and Newcastle's 'profit and loss' figures looking particularly rosy, Alan Pardew has pleaded with Ashley to open the biscuit tin and release funds.
Since January Newcastle have made a staggering £49m in transfers OUT ... and only spent £7.5m on transfers IN.
In an effort to get the men Pardew wants - at the prices Ashley is prepared to pay - is proving a gamble. But no-one loves a gamble more than casino-adict Fat Mike.
It represents a high-risk strategy, but with other clubs knowing the Toon have £35m in the bank from the sale of Andy Carroll, Alan Pardew feels he is being quoted (what he believes are) inflated prices.
Sadly it could yet amount to a case of who blinks first.
Pardew is desperate to sign a left-back and travelled to Holland on Sunday to watch Erik Pieters in action for PSV Eindhoven.
The Magpies are yet to meet PSV's asking price - the two clubs remain some distance apart in their respective valuations - although the player has indicated his interest in the move.
Pardew could yet make a loan move for Manchester City misfit Wayne Bridge, although Ashley has insisted the player (aged 31) is too old to be considered for a four-year contract (which is what the former Chelsea defender wants).
Ashley will only "buy" players who will have a sell-on value when the contract ends.
Ashley's strict wage structure is another problem Pardew has to overcome ... ruling out genuine WORLD CLASS players.
It's the 'bargain bin' once again, I'm afraid.
Also, Pardew does not have the pulling power of a Kevin Keegan or Graeme Souness - two managers well known worldwide for their abilities as players and managers.
Pardew - in the world of football - is a nobody, managing a club that is notorious for sacking managers.
So he has to battle away trying to prove that all is well in a club that has its fair share of problems ... OFF the pitch.
Saturday's morale-boosting derby victory at Sunderland took the Toon to the heights in the league ... and for the coming week alone ... that could be very important trying to bring in new faces.