Even then. As I say, it's the opposite of the image he's trying to sell, and I think he sees that image as integral to United's continuing financial success (which it is his job, after all, to safeguard.) He wants us to be the club making the big money buys, not the other way round.
Also there's no way in a million years Madrid would offer that sort of cash for a keeper. Especially since, as Annahnomoss says, opinion in Spain hasn't even really caught up with where De Gea is at the moment. He's still seen as the precocious youngster, the next in line national keeper. Their big money signings are about hype, and that means going for the in-fashion forward, like James last summer.
Technically no. But we have the financial might these days that if Woodward wants to keep him, he can offer him more than enough to do so. Maybe that wouldn't be a cast-iron guarantee if De Gea was a childhood Real fan, or had come from their academy, or was unhappy at United, or if we weren't going to be in the CL next season.
But he's clearly happy here, he's an established star and fan favourite with us - with the security of knowing that we won't drop him at the whim of the fans, or a dressing-room clique, or some new club President - we're headed for Europe, and he's got no particular attachment to Real.