Harry Mudd
In Star Trek: The Original Series, Harry Mudd was presented as a straight-up con-man, a dude who seemed to be okay with profiting from prostitution (in “Mudd’s Women”) and was also down with marooning the entire crew of the Enterprise on a random planet (in “I, Mudd”). He’s not a good person. Not even close. But, he does make a pretty could case against Starfleet’s lack of planning. In the Discovery episode “Choose Your Pain,” Mudd accuses Starfleet of starting the war with the Klingons, and, as a result, putting the larger population of the galaxy at risk. “I sure as hell understand why the Klingons pushed back,” Mudd tells Ash Tyler. “Starfleet arrogance. Have you ever bothered to look out of your spaceships down at the little guys below? If you had, you’d realize that there’s a lot more of us down there than there are you up here, and we’re sick and tired of getting caught in your crossfire.”
Seska
At a glance, Seska seems pretty irredeemable. She joins the idealistic Maquis but is secretly a Cardassian spy. Once in the Delta Quadrant, she tries to screw Voyager as much as possible, mostly by hooking up with the Kazon. That said, Seska is also someone caught up in hopelessly sexist, male-dominated power structures and does what she has to do to gain freedom and power. The Cardassian military isn’t exactly enlightened nor kind, so the fact that Seska was recruited into the Obsidian Order in the first place certainly explains her deceptive conditioning. You could argue that Seska could have become a better person once she had Captain Janeway as an ally, but, the truth is, she was still a spy caught behind enemy lines, but suddenly without a government to report back to. So, Seska did what she had to do to survive, even lying to Chakotay about having his child. The thing is, again, outside of Starfleet, Seska is at the mercy of the sexist machinations of the Kazon, so again, she’s kind of using all the tools at her disposal to gain freedom. Had Voyager not gone to the Delta Quadrant, and Seska’s villainy may have been more clear-cut. But, once the reason for her espionage becomes moot, her situation gets more desperate, and, on some level, more understandable.
Charlie Evans
In The Original Series, Kirk loves telling humans with god-like powers where to shove it. In “Where No Man Has Gone Before,” he phasers Gary Mitchell and buries him under a rock. But, in “Charlie X,” when teenager Charlie Evans also gets psionic powers, Kirk does a less-than-a-great job of being a good role model. For most of the episode, Kirk tries to avoid become Charlies’ surrogate parent, and when he does try, it results in an embarrassing overly macho wrestling match featuring those famous pink tights.
Charlie was a deeply troubled human being, and there was no justification for him harassing the crew and Janice Rand in specific. But, angry, kids like Charlie have to be helped before it gets to this point. Kirk mostly tried to dodge the adult responsibility of teaching Charlie the ropes, and only when some friendly aliens arrived, did everyone breathe a sigh of relief. But, don’t get it twisted, those aliens are basically just social workers, doing the hard work Starfleet is incapable of.
The Borg Queen
Because the origin of the Borg Queen has dubious canonical origins, all we were told in Voyager is that she was assimilated as a child, just like Seven of Nine. As Hugh and Jean-Luc discuss in the Picard episode “The Impossible Box,” basically, everyone assimilated by the Borg, is, on some level, a victim. The Queen was never presented this way in either First Contact or Voyager, but, at one point, writers Judith and Garfield Reeves-Stevens had pitched a story for Enterprise which would have featured Alice Krige as a Starfleet medical technician who made contact with the Borg.
Because both Alice Krige and Susanna Thompson played the Borg Queen, it’s possible the backstories of each Queen is different and that maybe they aren’t the same character. Either way, assuming the Borg Queen retains some level of autonomy relative to other drones (likely?) then she’s pretty much making the best of a bad situation. In fact, at the point at which you concede the Borg are unstoppable, the Queen’s desire to let Picard retain some degree of his independence as Locutus could scan as a kind of mercy. The Borg Queen actually thinks she and the Borg are making things simpler for everyone. And with both Data and Picard, she tried to make that transition easier and, in her own perverse way, fun too.
