I do think this is an interesting little conundrum. And I can see all the angles suggested so far. My view is:
I am about 150% certain that Kimmage is not doing this to toe the News Intl line, as other posters have pointed out in other threads, if Murdoch sacked him, he is such a respected journalist he would find another job in about a minute.
(That said, it does no harm to focus on the team your boss is sponsoring, even if you arent going to compromise your integrity)
I wonder if Kimmage thinks Wiggins actually has a chance? Even if its just the podium, because with Sky money behind it, if he does do really well, then it would quickly become a huge story.
Whatever Kimmage says from time to time, cycling is in his blood. He cant leave it alone.
EDIT: I just realised I didnt answer the OP.
I think to go further with the Clinic type questions with Brad would be unproductive. Wiggins is too savvy, and I dont want to know tbh. I think there are some interesting questions to be asked of DB vis a vis Barry and Sean Y (not that is any real proof, but...) and then compare with Garmin's philosophy.
i would also ask DB if he would sign Cav.
And I would ask some of the more seasoned pros eg Flecha and Arvesen what they think of the young Brits and how far they can go.
I would also kimmage to do the full broadsheet heavy interview with EBH, I know very little about the guy outside of his results and would love to know more about him. He seems talented and instinctive but still naive - in a nice way.
FURTHER EDIT: I would like to think that Kimmage has moved past his own problems with the sport and the JB/LA stuff and can look forwards. What i love about Kimmage's cycling journalism is that his own narrative is so caught up in it, it makes for such great stories and subtext. IF the Sunday Times want a journo on the LA/JB takedown side of things then they can put David Walsh on it.