These particular examples are not making the point you think they are, If these are the burning items in your craw, you should probably step back for a bigger picture.
I had to look up Nick Anderson. He had a cup of coffee in A ball with the Twins and is a decent major league reliever at best. Half the league has a similar story.
Logan Morrison was a one year $7m flyer that didn't work out but they rode out the year, same as Gallo. Big deal. Morrison, by the way, they stuck with all the way to his last appearance on August 10th. Hip injury, second time on the IL with a hip injury that was likely bothering most of the year. They took a one year flyer on a guy who got injured. Half the league has a similar story.
The Martin Perez/Randy Dobnak/Chris Archer/Dylan Bundy/Micheal Pineda/JA Happ/Rich Hill/Lance Lynn/Addison Reed/Bartolo Colon/who did I miss era doesn't have much to do with benefit of the doubt on hitters but it will help me illustrate my point. These pitchers were stepping stones to where we are now, which is undoubtedly better than where we were.
If you chose to remember a Nick Anderson and it gives you a visceral reaction you are not thinking clearly in evaluating the front office. In one breath, you say all front offices are wrong all to often. In the next you give fringe examples as defining moments. If we step back for a larger view, there is not one area of talent that is not markedly better than it was 5 years ago. If we look at the bigger picture, I have quite a lot of faith in them to get it right in the long term.
I've been reminiscing quite a bit lately and found the below thread from 2019 a few weeks ago. Quite interesting to read back and the discussion is basically the same, just the names are different. Spoiler, Lamonte Wade and Akil Baddoo are featured prominently (insert Spencer Steer and CES to modernize) Does anyone really miss those guys? Compared to the current roster? No, absolutely not.