From a pure prospect rankings sense, there's been some intentional trade-offs that have been made. In the last 30 months they've traded elite prospects(Jimenez, Torres) and Top 100-caliber depth(Cease, Candelario, Paredes) along with promoting and using Top 100 players(Contreras, Almora, Happ). We're also 1.5 seasons since the 2016 draft where the Cubs didn't have a pick til the 3rd round, which is a sweet spot where most high picks still have the potential to stick on lists before reality smacks them in the face, so this will likely represent a floor in terms of prospect depth on lists. As far as non-first round pick draftees go, I think it's fair that they haven't had as much success as they want or we would hope they'd have. They did go very pitching heavy outside the high first rounders which itself is going to ramp up the variance, and the shuffling they did with Benedict and their quotes about improving their development of young pitchers indicates they think they can do better there. They also have started getting comp picks again, this past draft they had one for the first time since their first draft in 2012 and they'll almost certainly get 2 this year. That's always been a part of the draft success they had in Boston(e.g. the 2005 draft where they had 6 of the Top 60 picks and got Ellsbury, Lowrie, and Buchholz) so hopefully it continues.