He will do everything he can to give his players what they want, much like Riola. The difference is that Riola understands that you can't completely burn all bridges with the clubs.
He will use any means to contradict negative claims about his clients. In the Liverpool case, media/fans painted a picture where he owed Liverpool and Rogers for developing him, and after his extra Christmas break. As a result Ward attacked exactly those topics and instead of keeping discussions behind closed doors, made a spectacle.
The Berahino situation was also dragged out in public.
So far the strategy has served Sterling well, I just think it is a poor strategy in the long run.