Whilst there maybe financial circumstances to suggest that there could be certain conditions that ashley would sell, the evidence would suggest it’s not likely.
Open to conjecture, but to me:
He has no history of selling much, if anything, that he acquires. Be that his ego, financial counter-arguments, whatever - there is no evidence he is willing to sell. There is evidence to suggest he is not willing, however.
His relationship with NUFC is wholly parasitical. Parasites don’t relinquish their grips on their hosts whilst the host is still breathing. Despite the horrendous running and plight of the club, there’s still breathe in it.
The club has allegedly been for sale for years. ashley is the reason it has not been sold. Because he doesn’t want to sell it. Other clubs have been sold - some twice over - during ashley’s association with NUFC.
Retail, as Rexn identifies, is his domain. I suspect the stumbling block centres round that, with Ashley insisting on ongoing rights regarding club merchandise and advertising. This is why a deal had not been done “overnight without anyone knowing”. The latest group have allegedly been in talks for over 4 months. I suspect they leaked to the WSJ out of desperation trying to hold ashley’s feet to the fire so sick of waiting for that “overnight without anyone knowing”.
Nobody is going to spend over £350M on a football club without getting full autonomy on how they run it thereafter. Ashley’s likely caveats concerning retail and marketing will always prevent a sale unless it’s to someone like kenyon’s consortium (Ashley’s supposed preference) as he’d likely go with that, which would benefit only him and ashley while the club remains crippled.
He’s used NUFC to prop up his other interests and promote his tat. Why kill the cash cow?
The only power is with the fans to boycott. Ashley made a unique move to counter recent efforts with mackem-style freebies that the sheeps’ friends have taken. It’s costing him money, yes, but this is just a dent at the moment whilst the club survives in the prem league as that is dwarfed by tv revenue and free global publicity for his tat. He needs a full stadium for the reasons stated on here countless times.
I said years ago that, failing a sustained, fully supported boycott to make a statement to the world, relegation and a sustained period outside of the top flight was the only chemotherapy to the cancer that is ashley.
Imo Rafa Benitez, either naively (I doubt) or by design kept the club up, which ultimately, by default, served no purpose to anyone but ashley. As Benitez was so revered on the terraces (despite the awful product on the pitch) there is a large slice of irony with that.
Above all else, you’re dealing with a cold fish who just sees the margins. There is no need to add risk in expenditure to improve when you can bump along the bottom with the likes of Bournemouth, Burnley and other also-rans quite nicely thank you very much.