I've mentioned this before, but my pre-season take was that the youth of the organization would determine how far this team goes. That's still true. I don't think that they intended to be leading the division for most of the year to this point. I think they tried to keep the valley as shallow as possible and worked to set up a good run next year, but I don't think they planned on being as competitive as they have this season. The Correa signing was a win/win in any situation. They needed a SS, potentially for just one season. They signed him to a deal that I don't think anyone seriously sees playing out to completion. The Lewis injury complicates that considerably. But the way the staff was built does not scream WS title contender at all. Injuries have decimated that plan in my view, but it wasn't set up to do a lot of damage in the first place. Partly due to injury, partly due to ineffectiveness, I don't think the pitching evolved they way that had hoped.
With all of that, you have this strange dichotomy of an absolutely brutal division that leads to a pretty average team leading the division for 4 months to this point. So they've put themselves in a situation where they find themselves on the doorstep of a divisional title, an IL full of trade chips and guys that they'd hoped to contribute now, and in serious need of pitching help. I'm not sure that they completely failed, I just don't think the season has played out in a way that they saw it unfolding. The injuries this team has suffered the last couple of seasons is astounding and has impacted organizational depth, but they haven't really had many, if any, minor league players jump up and fill a void when needed either.