Ben was the GM when Pablo was signed. While this signing reeks of Luchino et al, we have no way of knowing who made the call other than to assume that Henry approved.
At the same time, because Cherries was the man in charge of the roster at the time, the signing falls on him. If he wanted Pablo then it's on him. If he did not want Pablo, he should have been far more vociferous in his objection to the idea.
So f*** him and the horse that he rode out on.
In any case, Pablo has f***ed up at every turn while a Red Sox. It was a horrendous signing. It had failure written all over it before it happened. His declining stats the three previous years are evidence enough of that. Even if you ignore his obesity.