After the disaster Roark contract and the bad Grichuk deal. If this FO has a weakness so far, it's clearly in evaluating projections and placing the right value on middle-of-the-roster type guys.
They do great with the bargain bin bums (Ray, Matz, maybe Garcia) and with the elite guys (Springer, Semien, Gausman) but they've made all of their mistakes in the mid-tier.
They also haven't extended any of their young home-grown guys yet. If something doesn't change there, that could also end up looking like a pretty bad fault.