I've spent more time than is healthy analyzing and thinking about what went wrong with Ben.
The thing I keep coming back to is what he did differently than Theo. After all, they had a similar approach to player development, to analytics, to financial flexibility, and so forth. Which makes sense as Ben worked for Theo for a dozen years or so. And yet, Ben made a considerable number of moves that Theo probably NEVER would have in a million years.
And all I can think of is this: Ben sucked at one of most important things about being the GM in Boston: managing up. In particular managing Lucchino but also Werner.
Right from the get go with Sveum, Ben was overruled by management. They simply didn't trust him with the keys to the car. And even as he did probably earn their respect—World Series don't grow on trees—I'm not sure they ever thought of him with the regard they did Theo. And to that point, I'm not sure he ever had the cache to push back against their more harebrained ideas – like trading for "major league ready talent" in '14 or signing guys in '15 like Hanley and Pablo to make the team more marketable. I don't worship at the guy's alter exactly but as Tito's book confirms, these are the kinds of things Theo fought off constantly – mostly with success. Ben just didn't have the juice or respect in their eyes to do it – so as a result we got this weird, underperforming front office that seemed to lurch from one philosophy to another.
Ben's folly is that he could never get out from the shadow of Theo. The hiring of Dombrowski is certainly meant to correct for that.