They signed the cheques. That's all we know. Maybe nobody was really sure what they were doing. By August 2015 JH was obviously unimpressed with the results.
Then you took it a step further and said you were certain this plan was approved by ownership. That's getting a little carried away with your own idea.
I don't know where you get the idea that Ben had a "5 year plan". Are there any quotes about this?
The simple explanation for why Ben got canned is the back-to-back last place finishes. But there may have been other stuff going on that we don't know about. There may have been 'philosophical differences' between JH and Ben. There may have been specific moves Ben made that JH disagreed with. For example, maybe it was Ben who sold the front office that Hanley would be just fine in left field. Like I say there's a lot we don't know about.
The only explanation is that they were hoping for the 2013 Masterson and hoping the 2014 version was injured. But if he was injured in 2014 he was still injured in 2015. It was a bad signing to be sure.
I don't think I've ever seen a real doghouse - not for a long time, anyway. But like most married guys I know what it's like to spend some time in the figurative one.
I lived with those 1975-1978 teams too, and they were great teams, the most star-studded of all the Sox teams I've seen for sure. But they were tragic. And the loss in the 1978 playoff game was the end of the dream.