Cloughy has propably done all he can to keep the lad, apart from the main thing and that is to play him, and by playing him i mean a run in the side like Scouggs or Baxter has had. Now whether or not he has deserved a spot in the side at some point in the season is up for debate, but ultimately it's upto Clough himself. Me personally, thought he did deserve a bit of a run earlier on in the season as we weren't pulling any trees up really was we? Now we could've had more points if he'd have played, or less points, who knows? I personally don't think we could have been on much less if he had played more of a role this season as he does offer you that bit of a difference when required, as proved at Preston when given a decent opportunity against a decent side, not just 10 minutes like he has been given on a couple of occasions, that's what some of our fans like to judge him on, that's stupidity!
Ultimately, what i'm trying to get at with this agenda is that nor Cloughy or Diego are to blame in any of this so there shouldn't be one. Clough has offered him a contract, he's declined, what for we don't really know, but we can all have our guesses or assumptions as you rightly say. FOR NOW, mine is that the lad wants to play football, that could change but this is what i see now.
metalblade makes a good point that he could sign the contract and still play at York, but if Diego doesn't think Cloughy fancies him, and maybe Cloughy has offered him a shite contract in his mind, then he just might see his career elsewhere, which for me would be a shite way for a lad that's been here 13 years, that our coaches have brought through, to end this lads career for us.
Just one other thing, and this isn't directed at you mate, but them people that say if is name was something like Jack Smith or what ever, that he wouldn't even be mentioned, that has to be the biggest load of shite iv'e ever heard.