Epstein and Ryan aren't comparable. Ryan is taking back over a mess he has a large hand in creating. Epstein was taking over for a previous regime that made awful decisions. Epstein also had virtually nothing to build around whereas Ryan had Mauer, Sano, Kepler, Rosario, and others already on his team when he started a second time. We'll see if Epstein can build the Cubs back up from the husk that he inherited. But Ryan had a much more favorable position coming in, the comparisons aren't fair you're using. As for Ryan himself, it is a problem that Ryan is afraid to make big trades like the ones you mention. He's resistant to dealing premier talent and resistant to dealing for it. I'd argue that one of the reasons he doesn't make a lot of mistakes is he doesn't take any risks. The question you have to ask is - if other GMs can take risks and avoid major mistakes - does Ryan not do it because he's not as competent as those GMs at avoiding mistakes? Ryan gets a lot of credit for not making back-breaking decisions, but one could argue he only avoids those because he's little more than an average GM whose aware of it and avoids exposing it. In my opinion, it's ok to expect successful risk-taking from a "good" GM. We should demand that of Ryan as well.