I always looked at it more as poor asset management more so than trading a bunch of future stars away. There's a saying that Dombrowski always gets his guy, whether that's a trade or signing, but there's a cost to that.
Let's use home buying as an example. Let's say a house is valued at $500k, but you come in and buy it for $600k. That's fine, but there's an opportunity cost of that difference of $100k. Maybe you have to replace the roof or septic system, but now you don't have the money for it because you overpaid for the house.
That's how I look at Dombrowski. As
@GatorMike said, by the time he left, there wasn't much of value in the farm and the payroll was maxed out with unmovable contracts. It's not about those prospects as contributors to the roster, it's about their value as assets and what you can utilize those assets for, whether that's direct contribution or trade.
I look at Sweeney the same way with the draft and draft picks. When you draft players that others don't value as highly as you do, you end up having to use other assets to build the team, which is then exacerbated by overpaying to get deals done, and you slowly dig yourself a bigger hole that's difficult to climb out of because eventually you don't have enough assets to solve your problems, which is the issue they've run into this year where between cap overages and lack of draft picks, it will be difficult to improve the team.