I suspect at this point he was deliberately trolling and that's why he thought it was a good idea.
I actually think this is a very staged office. The office always looks the same for every photo-op. It is probably set up and used just for that purpose. His media handler sets up what is known as an 'environmental' image that is created to portray the feeling the client wants. Every paper, ever picture, set up for a purpose. Note that the office has changed little, including the specific piles of paper, from a photo shoot months ago.
[img width]http://i.dailymail.co.uk/i/pix/2015/08/21/00/2B88193900000578-0-image-a-1_1440114812533.jpg[/img]
...and from a few years ago...
...and...
...and what looks like a decade ago based on the meta data....
That newspaper might have been sitting there for a couple of decades as part of the staging when a photo is needed.
Remember, everything about him is about his image. He has been wearing the same two suits and 3 tie colors for decades. He is a brand and he has his own branding guidelines, including what looks like the staged messy office.
