Not sure any club can afford his price at the moment, plus he has been performing mostly well recently. I don't think him staying will be a surprise.
But he's only one year left on his contract. Staying one more year is not that difficult. In just a few months, he's free to talk to other clubs, even signing pre contract with clubs abroad. So even if he may have desire to stay, it's better for him in negotiation tactic to delay until January and look at options, and use that to counter offer our offer.
Raiola is too much an experienced and cnut negotiator not to see this. How he dragged out Zlatan renewal with Milan to get the best deal possible despite it's clear as day Zlatan is staying, I am positive this renewal wouldn't be agreed anytime soon, even if secretly Pogba wants to stay.
Only interesting thing whether Woodward stepping down before New Year, and uncertainty regarding the new United boss would hit a nerve on Raiola? Woodward may be easier to get schooled into giving in to craziest of demand by Raiola, but greed may mean Raiola want to drag this out, even if it means the new boss may be a tough nut to crack.