Fans of Cherington would exonerate him for the last place finishes and the lack of quality pitching throughout the organization. Giving him a pass on big money acquisitions that need owner approval is one thing, but roster management throughout the organization is another. The GM alone is responsible for who gets promoted and for identifying which are trade chips, etc. He is responsible for maximizing the value of the assets in the organization. No one else can be blamed for that.
IMO, the big $ acquisitions get approval at the highest level, but the recommendations for those moves usually do not. Certainly, Ben had input, and he either acquiesced or failed to persuade. Either way, he gets an F.