(TNG : The Nth Degree)
This one was super annoying to me. The dude had reached a new pinnacle in human existence and only wants to make completely benevolent technological leaps and bounds for organic life in terms of interstellar travel and likely usher humankind into a new plateau of being itself. Picard and the crew of the Enterprise in this episode end up looking like vengeful children trying to claw back power because they refuse to even consider the bigger picture here. At the very least they should have tried to learn from and negotiate with Demi-God Barclay on even the most basic improvements to the ship, to the organization of Starfleet and civilization, and to organic life all together. The episode fizzles out by the end and Barclay willingly just expunges the tech, and the knowledge that came with it, from his being, but I can't help but feel like he did so because of the inane and raving protests from his commanding officers. How short-sighted and selfish Picard and co were to independently declare that the current level of technology being employed by Starfleet and star-faring organic life was just the right amount of tech and that we should just forego any further alleviation of suffering for organic life. I get the criticism that Barclay in his new AI-increased form was moving FAST, as sapient AI would, but there wasn't an ounce of malevolence in his actions or words.. Honestly I think a human-turned-AI is far more trustworthy in terms of human interests than a pure AI like Data who they trust with their lives every single day.
Aaannywaaayyyss, this is just one of countless examples where I think Starfleet or its Captains were straight up stupid. What's your favorite example?