If he doesnt sign but stays then its a lose lose for all parties as fans will get on his back, he may struggle and have a poor season with no chance of making the England squad. Then the club loses a homegrown talent for nothing. But we also shouldn't sell him for a low price last minute either.
Rather than say he will be sold and give buying clubs leverage, bidding low as they know we want to sell, or waiting until the end of the window. We should tell him and his agent that if we dont get a reasonable offer (and im not talking £40 -£50mill) soon then we are prepared to let him see out the final year. There is no way imo he will want that.