The wider pictures is that we are at war with Real, and I don't think that's putting it too strongly. We continuously destabilise their players by bidding for them - even though we know full well they're only playing along to get better contracts. They routinely grab our world class players, or ones we were after. So if it's a war, we're losing.
The big picture here (I think) is that Woody is trying to change that dynamic by getting in their faces and playing hard ball whenever he can, even if it costs us money. After all, we have more of it than they do, and that's our one advantage.
So I wouldn't be surprised if we were equally at fault in the De Gea contract not happening.